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Just as vinyl has experienced a renaissance over the years, so has the humble cassette tape, beloved by Gen-Xers and the vehicle for crafting one of the most intimate forms of expression… the mixtape.

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Played endlessly until you know every skip, crackle, and pause, a mixtape may get lost, but the songs on it are never really forgotten and instantly transport you to the time, place, and person who made it.

There is an acknowledged art to making the perfect mixtape, one that’s been immortalized in the film adaption of Nick Hornby’s novel High Fidelity, with John Cusack pontificating on the subtle intricacies of making a mix: “Making a tape is like writing a letter – there’s a lot of erasing and rethinking and starting again. A good compilation tape, like breaking up, is hard to do.”

Making a mix can communicate any feeling you want, without having to put anything into words – other than a catchy title. Speaking of which, a theme is essential. Mixtapes are not playlists, they need to be cohesive rather than just a jumbling of songs. So what are the rules – or, rather, guidelines? When it comes to affairs of the heart, there are no rules.

So, with Valentine’s Day right around the corner, scroll down to read our guide to making the perfect mixtape for each stage of courtship.

Three important things to remember

First, make it personal. Mixtapes represent not only songs you like, but selections you think the recipient will love. Even for the romantic sadomasochists, there’s Danzig’s “Devil’s Plaything.” Consider the genre, but don’t be afraid to mix things up. There is a certain amount of peacocking that goes into tape curation, but don’t go too obscure just for the sake of it.

Secondly, there are general organizational rules of thumb: avoid including more than one track by the same artist, or two versions of the same song back to back (though covers are welcome). And avoiding excessively long tracks, there’s a beauty to sticking to analogue tape limits.

Thirdly, try to avoid the big hits. Not that Top 40 music is inferior, but more because he or she can just turn on the radio if they want to hear what’s charting on Billboard. Moreover, never underestimate the importance of flow. You can’t follow Mazzy Star’s “Bells Ring” with “Love Song” by The Damned. And when all else fails, go for a song with a girl or boy’s name in it.

While this labor of love no longer involves supreme patience and a tape machine, you can still make a “mixtape” no matter the format.

First Crush

This is perhaps the trickiest tape mix of all. How do you make your intentions clear without overwhelming the target of your affection? You can’t kick off a tape with The Smashing Pumpkins’ “Ava Adore,” you have to work your way up to it. For the non-committal types, there’s Rufus Wainwright’s “Vibrate,” which promises undisrupted attention; or for the heart-on-your-sleeve types there’s “No.1 Fan” by The Beautiful South. If you’re one of the many who couch their feelings in satire, you can use Bill Baxter’s “Embrasse-moi, Idiot!” and let him or her figure out the lyrics.

While you can’t go full torch song yet, it doesn’t mean you can’t get a little soulful, maybe Raphael Saadiq and D’Angelo’s “Be Here”? What about those looking to turn a friendship into something more? Jurassic 5’s “Thin Line” covered this dilemma and then some. And if you want to be really obvious, there’s always Lil’ Kim’s “Crush On You” or Sophie B. Hawkins’ “Damn I Wish I Was Your Lover.”

Early Dating

So your tape has succeeded and you’re dating. Congratulations! You’ve already set the bar high and now you’ve trod into equally slippery territory, where you’re a couple but still figuring out how serious you want to be. Pre-declaration of the “L-word,” opt for something beautiful and evocative: “I have searched for all your fragrance in the silent dark/Is that OK?” The Clientele’s “We Could Walk Together” conveys poetic longing while avoiding cliché, while Stephen Merritt of The Magnetic Fields can always be counted on for a sardonic love tune – after all, he did write a triple-album called 69 Love Songs.

When you’re are at the stage of professing love, there are decades of love songs at your disposal. But a mixtape is all about avoiding the obvious (sorry, “Sunshine, Lollipops, And Rainbows”). Love can be a strange and disorienting thing, and nothing captures that more than Pulp’s “F.E.E.L.I.N.G.C.A.L.L.E.D.L.O.V.E.” “Oh yeah, all the stuff they tell you about in the movies/But this isn’t chocolate boxes and roses – it’s dirtier than that.” Jarvis gets it. Not all love songs require lyrical gymnastics, case in point: Alex Chilton’s pie-eyed vocals on Big Star’s “I’m In Love With A Girl.”

Traditionally, the mixtape is often flush with 80s and 90s music due to the advent of tape decks and the almighty Walkman, but that’s not to say you can’t get some 70s funk on there and dip into other decades. Syreeta’s bass-fuelled cover of Stevie Wonder’s “I Love Every Little Thing About You” is one of the most delightful love songs on record; it’s a true mystery why her solo career never fully took off.

Serious Relationship

This is where you can really flex your mixtape muscles, crafting an impeccable mix for your significant other. You know their likes, their dislikes and can include songs that hold special meaning in your relationship. But if you’re ever in doubt, a soul song can always move the heart. Irma Thomas has been getting a lot of action lately due to her 1964 song “Anyone Who Knows What Love Is (Will Understand)” cropping up in TV and film – notably the fourth season of Charlie Brooker’s Black Mirror – but her earlier release, “Ruler Of My Heart,” is equally stirring.

Cover versions are great for mixes because they allow you to experience a song you’re familiar with in a new way. While Brenda Holloway sings the hell out of “You’ve Made Me So Happy,” Lou Rawls’ silky vocals take it over the top. Side-stepping the saccharine love songs of the adult contemporary dial, Glen Campbell manages to make grown men weep with his emotionally raw interpretation of Jimmy Webb’s “Wichita Lineman,” a blue-collar ballad that lays it all on the line.

Let’s Get Back Together

So you flew too close to the sun and now your relationship is a pile of ashes. Depending on how things ended, there might be a chance you can rekindle the flame the same way you started it – with a mixtape! The key to putting together a “take me back” mix is to lay all your cards on the table, even if it means the inclusion of James Brown’s “Begging Begging.” Sure, it’d be easy to just fill both “sides” with Hank Williams and call it a day, but you can catch more flies with honey.

Let the smooth vocal harmonies of the Gibb brothers wash over him or her on Bee Gees’ “You Know It’s For You,” which seeks to win over the heart through perseverance alone. Or you could leave it up to Roxy Music’s “All I Want Is You” to win them over. After all, Bryan Ferry has always had luck with the ladies. And if your break-up was more misunderstanding than a result of egregious errors, Angel Olsen’s “Shut Up Kiss Me” cuts right to the heart of the matter.

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Motown wasted no time getting Teena Marie back in the studio on the heels of her 1979 Rick James-produced debut, Wild & Peaceful. Her sophomore project had to dispel the notion that she was a singer in need of a svengali – she was, in fact, a prolific writer with her own ideas about how she wanted to sound. While Berry Gordy was afraid R&B listeners would assume she was a pop singer and thus keenly withheld her image from American pressings of her debut, it was time to show the world who she was; literally.

James encouraged Marie to take the reins of her own production, but she asked Richard Rudolph, producer and husband of Minnie Riperton, to co-produce the next album with her. Together, Rudolph and Marie combined seasoned studio musicians, like Paulinho Da Costa and Randy Waldman, with a new group of players from Nashville named Ozone, who arrived at Motown by way of Billy Preston and Syreeta, creating a sophisticated and buoyant profusion of soul, funk, jazz and pop sounds. On background vocals, Teena was joined by her sister-friend/collaborator, Jill Jones (later a protégé of Prince), Andraé Crouch & the Disciples’ Bili Thedford, Brenda Lee Eager, and others. Teena wrote all but one of the album’s nine tunes, the outlier being “Now That I Have You,” an octave-stretching ballad intended for Minnie Riperton, who died just before production on Lady T began in the late summer of 1979.

Listen to Teena Marie’s Lady T now.

“Aladdin’s Lamp” and the album’s first single, “Can It Be Love” were ballads that exhibited the unabashed emotional transparency that Teena would become synonymous with, singing of both the joys of newfound love and fresh heartache without inhibition. Uptempo cuts like “You’re All The Boogie I Need” and “Young Girl In Love,” meanwhile, were youthful and sassy, expressing the playful side of the poet.

From the swaggerific, bass-heavy opener “Behind the Groove,” which hit #4 on Billboard’s Dance/Disco chart, to the closer, the Marvin Gaye-esque “Too Many Colors,” Lady T introduced concepts that would develop in her work over the next 32 years: intergalactic travel, the vitality of a groove, emerald city love songs, and the quandaries of race and racism.

Lady T was a statement of self-possession. With its shoulders up, head-held-high cover portrait, soul-exposing back cover poem, and nine versatile compositions, the album solidified Teena’s relationship with a growing listener base, assuring them that she had only scratched the surface of her own creativity.

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Can it really be that long ago? In many ways, it feels like we’ve benefitted from Erykah Badu’s idiosyncratic style and lyrical insights since time immemorial; yet it also feels like only yesterday that Baduizm, originally released on February 11, 1997, made its creator a household name, taking her to No.2 in the US while cruising to the top of the R&B chart.

A confident mix of jazz, soul, R&B, and hip-hop, Baduizm was uniquely Erykah: the first offerings from a woman who’d been singing on local radio stations since the age of 14, and who, aged 25, contained a lifetime’s worth of experience in her vocal delivery, drawing comparisons to Billie Holiday while also being praised by the Chicago Tribune for having “an artistic vision as unique and independent” as Prince’s during his mercurial 80s heyday. Receiving the Best R&B Album award at the Grammys (as well as scooping Best Female R&B Vocal Performance for Badu’s R&B chart-topping debut single, “On & On”), the album also swept up accolades at the American Music Awards and Soul Train Music Awards.

Three years later, Badu followed her debut with an even more expansive album. Furthering her artistic exploration even while looking inward to develop deeply personal lyrics that resonated with her ever-growing fanbase, Badu loaded Mama’s Gun with neo-soul classics such as “Bag Lady” and “Didn’t Cha Know?” – cuts that more than earned their place among the era’s finest, and which still sound fresh as ever. Recently hailed by Pitchfork as “a Black feminist album that went well beyond documenting tales of heartbreak to address issues greater than the sum of any one relationship,” Mama’s Gun remains a landmark release. But Baduizm is where it all started – and Erykah herself remains the High Priestess Of Neo-Soul.

Erykah Badu’s Baduizm can be bought here.

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The Guild of Music Supervisors has announced their 16th annual Icon Awards honoree, legendary singer, songwriter, multi-instrumentalist, and producer, Raphael Saadiq. The Icon Award was created to celebrate those who have made legendary contributions to the music and film industry. Previous recipients of the Icon Award include Quincy Jones, Burt Bacharach, Kenny Loggins, Marc Shaiman, and Stephen Schwartz.

The 16th Annual Guild of Music Supervisor Awards ceremony takes place February 28th at the Wiltern Theatre in Los Angeles. Tickets are available to purchase now.

Raphael Saadiq offered the following: “I am honored to be the recipient of this year’s Icon Award. Music plays such an important role in how stories are told on screen and I have always believed in the power of music to deepen emotion and connect people to the story. To be recognized by a community that celebrates the important relationship between music and cinematic story telling means a lot to me.”

Lindsay Wolfington, President of the Guild of Music Supervisors, had this to say about Raphael Saadiq, “We are very excited to honor someone whose reach has touched so many parts of the music and media industries; Raphael Saadiq’s contributions as an artist, songwriter, producer and composer for visual media truly define what we celebrate with the GMS Icon Award.”

The recipient of this year’s Legacy Award, meanwhile, is Robin Kaye, former Vice President of the Guild of Music Supervisors. The Legacy Award is presented to a music supervisor who has made a lasting impact on the industry over the course of their career.

A founding member of the iconic R&B group Tony! Toni! Toné!, Saadiq went on to forge a trailblazing solo career with acclaimed albums including Instant Vintage, The Way I See It, Stone Rollin’, and Jimmy Lee. Saadiq has written and produced for D’Angelo, Solange, Beyoncé, Stevie Wonder, Mary J. Blige, and John Legend, among many others. Most recently, Saadiq co-wrote the original song “I Lied to You” (with Ludwig Göransson) for Ryan Coogler’s 2025 film Sinners, performed by breakout star Miles Caton. Saadiq received Golden Globe, Grammy, and Oscar nominations for “I Lied to You.”

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Each year, the annual Super Bowl attracts a massive audience at home and abroad, ranking second only to the UEFA Champions League final as the most-watched annual sporting event worldwide. Yet it’s not all about the sport. The best Super Bowl halftime shows have played host to spellbinding performances from the best rock and pop superstars over the past three decades.

With Rihanna set to add their name to the list, with a much-anticipated halftime show, we take a look at the best Super Bowl halftime shows of all time.

The Rolling Stones (2006)

Satisfaction guaranteed with the legendary group, tearing through classics like “Start Me Up” and “Rough Justice.”

Lady Gaga (2017)

Also featuring groups of hundreds of lighted drones in the sky over Houston’s NRG Stadium, Lady Gaga’s set included tracks from her album Joanne and an impassioned cover of Woody Guthrie’s “This Land Is Your Land.” The NFL claimed it was the “most watched musical event of all-time,” citing global viewing figures of 150 million.

Tom Petty & The Heartbreakers (2008)

The incomparable Tom Petty was at full tilt during this performance, slashing and burning through a four-song set including a yearning “Free Fallin’” and a supercharged “Runnin’ Down A Dream.”

Katy Perry feat. Lenny Kravitz & Missy Elliott (2015)

When you’re the halftime performer at the Super Bowl, all eyes are on you. Unless, apparently, you bring dancing sharks on stage like Katy Perry did during “Teenage Dream” and “California Gurls” at the 2015 Super Bowl. Left shark’s moves were…unpredictable, which caused an internet uproar, though one that also highlighted Perry’s electric performance and her brilliant decision to share the stage with Missy Elliott.

Michael Jackson (1993)

A barnstormer that set the bar for anyone else looking to compete with the best Super Bowl halftime shows: the self-styled King Of Pop performed an awesome mini-set including “Billie Jean,” “Black Or White,” and “We Are The World.” After this performance, the NFL actively pursued pop’s top names for their halftime shows.

Diana Ross (1996)

Diana Ross’ Super Bowl halftime performance featured an electrifying medley of Ms. Ross’ greatest moments from The Supremes (“Baby Love,” “You Keep Me Hangin’ On”), her solo career (“Chain Reaction”), and more.

Boyz II Men, The Temptations, Smokey Robinson, Martha & The Vandellas, Queen Latifah (1998)

An all-star Motown extravaganza, this Super Bowl halftime show culminated with the artists performing a show-stopping finale of “Dancing In The Street” with the GSU Marching Band.

U2 (2002)

In tribute to those killed in the 9/11 terrorist attacks, U2 performed an emotional mini-set featuring “Beautiful Day,” hymn of peace “MLK,” and “Where The Streets Have No Name.”

Paul McCartney (2005)

Paul McCartney was on suitably fab form for his Super Bowl halftime performance with a hits-stuffed mini-set of Beatles classics and his own James Bond theme, “Live And Let Die.”

Bruce Springsteen & The E Street Band (2009)

Tailor-made to slay stadiums, The Boss and his loyal cohorts rampaged through a quartet of all-American classics including “Glory Days” and “Born To Run.”

Madonna With MIA, Nicki Minaj, Cee Lo Green, LMFAO (Indianapolis, 2012)

This Madonna spectacular visualized by theatrical company Cirque Du Soleil and choreographer Jamie King set a new record for Super Bowl viewing figures, attracting 114 million viewers – reputedly more people than those watching the game itself.

The Weeknd (2021)

The Weeknd and musical director Oneohtrix Point Never brought the After Hours era to the biggest stage imaginable at the 2021 Super Bowl. Performing a medley of hits across his discography, Abel Tesfaye moved from the stage to a claustrophobic room filled with look-alikes ready to brawl, before emerging once again to serenade his global audience with “Blinding Lights.”

Beyoncé, Destiny’s Child (2013)

This highly acclaimed Super Bowl halftime performance generated more than 299,000 tweets per minute. At the time, it was reportedly the second most tweeted moment in the history of Twitter.

Coldplay feat. Bruno Mars and Beyoncé (2016)

Coldplay came with a number of tricks up their sleeves for the Super Bowl 50 halftime show. After running through seminal hits like, “Yellow,” “Viva la Vida,” “Paradise,” “Adventure of a Lifetime,” the group brought Bruno Mars and Beyoncé onstage to perform “Uptown Funk” and “Formation,” respectively, before everyone joined together for a rousing finale. Chris Martin was wise enough to know that inviting Beyoncé onstage is an automatic W. If only she could have helped the Carolina Panthers offense.

Prince (2007)

Torrential – rather than purple – rain threatened to make Prince’s Super Bowl XLI halftime performance a washout. No problem for one of the world’s greatest live performers, who shrugged off organizers’ concerns with one question: “Can you make it rain harder?”

Whipping up his own storm on a lit-up, symbol-shaped stage, Prince defied the elements to unleash “Let’s Go Crazy,” “Baby I’m A Star,” and “Purple Rain,” chucking Bob Dylan’s “All Along The Watchtower” and Foo Fighters’ “Best Of You” in for good measure. Come the finale, a full marching band had taken to the field, Prince had cycled through four guitars – one of which suffered water damage thanks to the strength of the rain – and 93 million people had witnessed a performance that is still hailed as one of the all-time best Super Bowl halftime shows.

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To say that 1999 was a year of excitement and uncertainty would be an understatement. The world waited expectantly on the cusp of the new millennium and, in the months leading up to Y2K, music fans had plenty of albums to enjoy.

While the pop landscape was flush with a broad array of boy bands, girl groups, and pop divas (including Destiny’s Child, Britney Spears, Backstreet Boys, and Christina Aguilera), the airwaves were also brimming with Latin rhythms. Buena Vista Social Club, a documentary about the Cuban music scene, gave legendary artists like Ibrahim Ferrer a new platform. Latin rockers Santana found a new generation of fans with their massively popular comeback album, Supernatural. Rising acts like Zurdok and Control Machete found new opportunities for crossover success, while Ricky Martin had everyone “Livin’ La Vida Loca.”

The air was ripe with possibilities for electronic acts as well, with Moby, Fatboy Slim, and Underworld finding mainstream success, while hip-hop fans had plenty of incredible music to choose from, thanks to great albums by Dr. Dre, The Roots, and Eminem.

From the Red Hot Chili Peppers’ Californication to TLC’s Fanmail, here are the best albums of 1999.

Can’t get enough 90s music? Listen to our 90s Music playlist here.

55: Julie Miller – Broken Things

The country-folk singer’s 1999 album is an emotional and intimate record that puts her stirring vocals and precise songwriting front and center.

54: Pépé Bradock – Burning

Taking inspiration from dance music of the 70s, the French producer’s influential work spins disco, breakbeats, and soul into an irresistibly danceable record.

53: Beck – Midnite Vultures

Taking inspiration from soul and funk music, the genre-blending artist’s 1999 album injects the styles with a humor and quirkiness distinctly his own.

52: Ibrahim Ferrer – Buena Vista Social Club Presents Ibrahim Ferrer

A follow-up album to the music documentary of the same name, the Cuban music legend’s comeback album revives the spirit of the golden age of Cuban music in the 50s and 60s.

51: Zurdok – Hombre Sintetizador

The Mexican alt rock band’s 1999 album is home to the hit single “Abre Los Ojos,” and established the band as one of the most popular regional bands of the decade.

50: Botch – We Are the Romans

The metalcore band’s final album incorporates experimental rhythms and esoteric lyrics to create a standout album of the niche genre.

49: Puya – Fundamental

The Puerto Rican metal band’s major label debut put rock en espanol on the map and proved that good music is a universal language.

48: The Chemical Brothers ‎– Surrender

The electronic duo turned to house music for their third studio album, threading the needle between the storied genre and the big beat sound they helped pioneer in their earlier releases.

47: Dillinger Escape Plan – Calculating Infinity

The metalcore band’s debut album is full of loud rage and technical detail, becoming one of the most inventive and influential releases of the genre.

46: Reba McEntire – So Good Together

Home to the crossover single “What Do You Say,” the prolific country star’s 25th studio album introduced her to a broader audience and cemented her status as a living legend.

45: Paul Bley, Gary Peacock, Paul Motian – Not Two, Not One

The jazz masters reunited after over two decades on this record which feels like a well-deserving victory lap and beautifully plays to their respective talents.

44: Opeth – Still Life

The Swedish metal band’s concept album has some of their best lyricism and memorable arrangements, establishing them as leading lights of the scene.

43: The Olivia Tremor Control – Black Foliage: Animation Music Volume One

Taking inspiration from musique concrète, noise, and pop, the band’s 1999 album eschews any easy categorization and will keep your head spinning from start to finish.

42: Dream Theater – Metropolis Pt. 2: Scenes from a Memory

The prog rock band’s 1999 concept album centers around a time-traveling murder mystery with music just as dense as the narrative. For patient listeners, the reward is great.

41: Underworld – Beaucoup Fish

After getting a big boost from a placement in the film Trainspotting, the group’s highly anticipated album exceeded expectations and became an instant electronica classic.

40: Moby – Play

Moby’s commercial smash streaks techno with hints of blues and pop, creating a sound that is both critically remarkable and widely accessible.

39: Dave Holland Quintet – Prime Directive

The famed double-bassist delivers pure, unadulterated jazz on this album – improvisational, meditative, and undeniably rhythmic.

30: Blur – 13

On this album Damon Albarn’s songwriting centers on the dissolution of relationships, producing one of the group’s most vulnerable records.

38: Prince Paul – A Prince Among Thieves

Featuring the likes of Big Daddy Kane, Biz Markie, Chris Rock, and De La Soul, the hip-hop producer’s concept album is a detailed and extremely rich model of musical storytelling.

37: The Beta Band – The Beta Band

The rock band’s 1999 album brings together pop, rock, hip-hop, folk, and much more for a chaotically beautiful debut.

36: Control Machete – Artilleria Pesada Presenta

The Mexican hip-hop group’s second album established them as a mainstay in Latin pop and opened the door for a number of cross-genre collaborations.

35: Macy Gray – On How Life Is

Home to favorites, “I Try” and “Still,” the distinctly bluesy rasp of Macy Gray was introduced to the world on this debut album.

34: TLC – Fanmail

The influential girl group’s third studio album includes the smash hit, “No Scrubs,” and would be the last album released during Lisa “Left Eye” Lopes’ lifetime.

33: Ginuwine – 100% Ginuwine

The singer’s Timbaland-produced album reshaped the sound of R&B by blending traditional soul with futuristic production.

32: Blackalicious – Nia

The Sacramento hip-hop duo’s debut album is at turns whimsical and abstract but always feels rooted in the tenets of underground hip-hop – booming beats and great rhymes.

31: Mary J. Blige – Mary

The R&B singer broke from her hip-hop roots on this album, showing that she has the vocal chops to tackle soul, traditional R&B, and pop.

30: Susumu Yokota – Sakura

The Japanese producer’s excellent ambient album doesn’t hide in electronic instrumentation, using it instead to highlight the beauty of simple guitars and piano.

29: Dr. Dre – 2001

Home to hip-hop classics like “Still D.R.E” and “Forgot About Dre,” the legendary producer and rapper’s comeback album took him from behind the boards and re-established him as a frontman of the genre.

28: Basement Jaxx – Remedy

Taking cues from New York’s house music scene, the British electronic duo’s debut album is a groovy, stylistically diverse take on dance music that will keep you moving from top to bottom.

27: Christina Aguilera – Christina Aguilera

Home to timeless hits like “Genie In A Bottle” and “What A Girl Wants,” the singer’s debut album established her as a vocal powerhouse with a knack for catchy songwriting.

26: Esbjörn Svensson Trio – From Gagarin’s Point Of View

Featuring the memorable title track, the jazz trio’s international breakthrough brought their distinct brand of jazz pop to a global audience.

25: Alison Krauss – Forget About It

Featuring fan favorites like “Ghost In This House” and “Stay,” the bluegrass singer’s stripped down 1999 album serves as a showcase for her masterful storytelling.

24: Neurosis – Times of Grace

One of their most fully realized projects, the Oakland death metal band’s uncompromising and challenging 1999 album is not for the faint of heart, but if you can get into it, you’ll never look back.

23: Backstreet Boys – Millennium

Home to the pop classic, “I Want It That Way,” the boy band’s third studio album catapulted them to global stardom.

22: Built to Spill: Keep It Like A Secret

Lead singer and songwriter ​​Doug Martsch turned to pop for the band’s second big label album, nevertheless he managed to pull off a more mainstream sound without having to hand over the group’s indie rock cred.

21: Drexciya – Neptune’s Lair

Steeped in mythology and mystery, the influential electronic duo’s debut LP sounds like nothing before it and is widely considered to be one of the greatest techno records ever produced.

20: Nine Inch Nails – The Fragile

Trent Reznor’s meticulous approach to arranging music reaches a creative peak on this record that encompasses everything from industrial noise to ambient instrumentals.

19: Rage Against The Machine – The Battle Of Los Angeles

Home to their biggest hit ​​”Guerilla Radio,” the rapping rock band’s 1999 album still sounds as revolutionary today as it did decades ago.

18: Red Hot Chili Peppers – Californication

Featuring the title hit and the Grammy Award-winning “Scar Tissue,” the band’s 1999 album saw them reuniting with guitarist John Frusciante and became one of their most successful releases to date.

17: Santana – Supernatural

The Latin rock band’s comeback album for Arista Records features some high-profile guests like Lauryn Hill, Eagle Eye Cherry, and Eric Clapton, and returned the veteran rockers to the public eye.

16: Nobuo Uematsu – Final Fantasy VIII

The video game soundtrack has taken on a life of its own, allowing longtime gamers and nongamers alike to find something to enjoy.

15: Ely Guerra – Lotofire

Spanning topics as serious as femicide and environmentalism, the Mexican singer’s hit album is a subtle yet potent record that showcases her understated vocals over trip-hop inspired production.

14: Mariah Carey – Rainbow

Including the forever party jam, “Heartbreaker,” the vocal titan’s seventh studio album is a pop R&B classic that conjures puppy love and summer days.

13: Dixie Chicks – Fly

The country group’s chart-topping album includes hits like “Ready to Run,” and “Cowboy Take Me Away.” With its diverse influences and sharp storytelling, the record paved the way for future female country pop stars like Taylor Swift.

12: Smog – Knock Knock

Bill Calahan’s affecting break-up album is understated, bittersweet, and utterly hopeful, showing that even in crisis, there is light to be found.

11: Kelis – Kaleidoscope

The pop R&B icon’s debut album was produced by the Neptunes, heightening the out-of-this-world energy of Kelis’s vocal delivery and daring storytelling.

10: Destiny’s Child – The Writing’s on the Wall

Featuring classics such as “Say My Name,” “Bills, Bills, Bills,” “Bug A Boo,” and “Jumpin’ Jumpin’,” the girl group’s sophomore album proved that they weren’t just pop savvy but also incredible vocalists.

9: The Magnetic Fields – 69 Love Songs

Comprising three volumes of music, Stephin Merritt’s ambitious record rejects surface-level romance and digs deep to uncover the good, the bad, and the ugly of romantic love.

8: Sigur Rós – Ágætis byrjun

With its dense arrangements and gorgeous melodies, the Icelandic band’s sophomore album took post-rock from a small community to a global phenomenon.

7: Sleater-Kinney – The Hot Rock

The rock band turned inward for their fourth album exploring the dark corners of the mind and relationships, showcasing their incredible range and storytelling skills.

6: The Roots – Things Fall Apart

The hip-hop band’s masterpiece is a prescient, invigorating, and critical album that continues to impress hip-hop fans decades after its release.

5: MF Doom – Operation: Doomsday

The late rapper’s opus is a swirl of dense lyricism and stellar production that makes it clear why Doom is your favorite rapper’s favorite rapper.

4: Britney Spears – …Baby One More Time

Home to the record-smashing title hit, the pop queen’s debut album remade the genre in her image and signaled a new era of teen pop stars.

3: The Flaming Lips – The Soft Bulletin

With the grandeur of an orchestra, the rock band’s masterpiece is deeply moving and widely considered to be one of the best records of the decade.

2: Mos Def – Black on Both Sides

Featuring beloved classics like “Ms. Fat Booty” and “UMI Says,” the Brooklyn rapper debut established him as one of the genre’s greatest lyricists.

1: Eminem – The Slim Shady LP

The rap veteran’s sophomore album includes the smash hit, “My Name Is” and introduced Eminem the supervillain to the mainstream; despite its controversy, no one could deny that it was one of the greatest major label debuts of all time.

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Whether you call him the King of R&B, the King of Stage, or something else entirely, there’s no denying Bobby Brown’s incredible impact on popular culture. Brown has been an unstoppable force since his early days with the iconic R&B group New Edition in his hometown of Boston during the 1970s. After a successful three-album run with the group, Brown started a solo career in 1985. The ups and downs of his personal life eventually earned him the title “the bad boy of R&B,” the music has always been the reason that folks cared. Here are 14 Bobby Brown songs that explain why he’s one of the kings of R&B.

Listen to Bobby Brown’s best songs on Spotify or Apple Music.

Bobby Brown, The King of New Jack Swing

Bobby Brown’s second record Don’t Be Cruel is the quintessential New Jack Swing album. The high power production from Babyface and L.A. Reid, coupled with Brown’s high energy, produced the best-selling album of 1989. Indeed, from 1989 to 1992, Brown had seven solo Top 10 hits and three Top 10 hits with New Edition. You can hear the influence of Brown’s classic New Jack Swing era persona in artists like Usher, Bruno Mars, Ginuwine, and many more. Here are the hits from that period.

Every Little Step

Although Bobby Brown spent most of the Don’t Be Cruel era shedding his New Edition bubblegum image, “Every Little Step” is a sweet love song co-written by L.A. Reid. Initially meant for R&B group Midnight Star, Brown fell in love with the demo after hearing it, immediately scooping it up for Don’t Be Cruel. The song peaked at No. 3 on the Billboard Hot 100 and earned Brown his first Grammy Award for Best Male R&B Vocal Performance.

Roni

Inspired by a young lady Babyface met in Florida while on tour, “Roni” is a fun ballad. The third single from Don’t Be Cruel breaks down what it means to be a “tenderoni.” What exactly is a Roni? According to the song, she’s the “sweetest little girl in the whole wide world, and she’d make the toughest homeboy fall deep in love.” The song peaked at No. 3 on the Billboard Hot 100.

My Prerogative

Along with Teddy Riley and Aaron Hall, Bobby Brown wrote this song as a response to the criticism he received following his departure from New Edition. The song was about ignoring the judgment of others. The song ultimately spent 24 weeks on the Hot 100.

Rock Wit’cha

Another ballad, this song is subtle but direct in its message. “How bout a little music now/Let’s hear some Marvin Gaye/Ooh, let me rub your shoulders down/Let’s take the night away.”

Don’t Be Cruel

The title track from Bobby Brown’s best-selling album shows how multitalented the singer really is. He’s singing, rapping, and dancing his ass off in the video. The song became Brown’s second No. 1 single on the R&B charts.

Something In Common

The first collab between Bobby Brown and Whitney Houston is a perfect mix of the roughness of New Jack Swing with the sweetness of pop, which aptly describes their public personas at the time. Hearing Brown and Houston singing about how much they love each other – despite being opposites – is instant dopamine.

New Edition Classics

New Edtion is where Bobby Brown got his start, and the group has always had a pull on him. Despite leaving to go solo in 1985, Brown has returned for both albums and tours. It’s easy to understand why. The group – at its best – had an enormous impact on both R&B and pop music. Almost every boy band that came after them owes them an enormous debt, whether they know it or not. Here are the best New Edition songs featuring Bobby Brown

Candy Girl

New Edition’s debut single “Candy Girl” is the perfect teeny-bop song. An inspiration for acts like N’SYNC and Another Bad Creation, it still sounds as fresh as ever.

Hit Me Off

New Edition reunited in 1996 for the Home Again album. “Hit Me Off,” the debut single, proved that the group still had it after 20 years in the game. And it only made sense that Bobby Brown would take the first verse. The song went gold in the US and peaked at No. 3 on the Billboard Hot 100.

Jealous Girl

A young Bobby Brown sings lead on this song about a bitter ex that’s envious of his new relationship. The song was the B-side to their Top 50 single, “Popcorn Love,” and a cult classic with core New Edition fans.

Mr. Telephone Man

“Mr. Telephone Man” was Bobby Brown’s first time singing lead at the age of 15. The song is about heartbroken boys that can’t come to grips with a break up delivered via phone. Instead of accepting the end of the relationship, they call the operator and insist there must be something wrong with the connection. The song peaked at No. 12 on the Billboard Hot 100.

Bobby Brown Deep Cuts

Every song can’t be a commercial success, but that doesn’t mean it isn’t good. When you’re an artist like Bobby Brown, you’re caught between a rock and a hard place. People expect you to stick to the formula that made you a superstar. But they also want you to come with sounding new. While most of these songs are B-side singles, they’re often not discussed when it comes to Brown’s legacy. They should be.

You Don’t Have To Worry

The third single from Home Again was produced by Stevie J, the late Chucky Thompson, and Diddy. Bobby Brown leads the charge on this song about fixing his relationship after messing up big time. His vocals on the song are reminiscent of his Don’t Be Cruel days. Missy Elliott appeared on the remix.

Feelin’ Inside

Although this single from Bobby Brown’s fourth album, Forever, failed to impact the charts, it’s a gem. The song is one part old school New Jack Swing mixed with a futuristic jazz sound. Whitney Houston stars in the video.

Two Can Play That Game

Thanks to the K-Klass remix, “Two Can Play That Game” became a hit for Bobby Brown in the UK, but the original version is just as lovely.

Girlfriend

This one goes out to the day one Bobby Brown fans. The debut single from Bobby Brown follows the bubblegum pop and R&B model that helped New Edition rise to the top. The song peaked at No. 57 on the Billboard Hot 100 and No. 1 on Billboard’s R&B chart.

Seventeen

Don’t let the infectious beat fool you; this song has a message. Bobby Brown sings about a teenager with a bright future who turns to prostitution after becoming a single teen mom. The song’s release was timely, as teenage pregnancy was then at an all-time high.

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To say that, back in 1985, Janet Jackson lived in her brother Michael’s shadow was something of an understatement. At that time Michael was at the height of his reign as the undisputed “King Of Pop” and was still basking in the success of his 1982 blockbuster album, Thriller. But that was before Control, the album that proved Janet Jackson had what it took to launch a formidable attack on the charts.

Initially marketed as a sweet-voiced ingénue, Janet had scored a couple of Top 10 R&B hits (“Young Love” in 1982, and, two years later, “Don’t Stand Another Chance”) in the US for A&M Records, but they didn’t reveal the outstanding natural talent that she possessed.

A career relaunch

A shock was in store. In January 1986, Janet Jackson relaunched her singing career on A&M with the single “What Have You Done For Me Lately,” a seismic slab of minimalist techno-funk driven by pounding a drum machine beat. It was both sassy and sexy, and dispelled the girl-next-door image that A&M had used to market her four years earlier. Helmed by ex-Time members Jimmy Jam and Terry Lewis – then the hottest production team in R&B, and masterminds of substantial hits for SOS Band, Cherrelle, and Alexander O’Neal – the song quickly shot to the top of the US R&B singles chart.

The keenly-anticipated parent album, Control, followed on February 4, 1986 and, a month later, it topped the US R&B chart, where it spent a jaw-dropping 91 weeks. Control eventually hit the top of the US pop albums chart and the Billboard 200, and transformed Janet Jackson into a megastar whose fame would rival Michael’s.

A make or break album

Despite its phenomenal international success, Control started out as a make-or-break album for Janet Jackson, who wanted a radical change of musical direction. “That was a point where it was like a crossroads for me in my career,” she told this writer in 2001. “If it wasn’t going to pan out, I was gonna go back to school. I was studying business law and I thought I would try music one more time.”

The album’s title stemmed from the fact that, before she hooked up with Jam and Lewis, Janet felt she had no control over what she was doing: she was like a producer’s puppet with little or no say in the direction of her music. “I wanted to do it differently than being handed a piece of music and told, ‘Here, sing this,’ which it was in the past,” she revealed. “I wanted to express myself, and Jimmy and Terry helped me to do that.”

Listen to Janet Jackson’s Control now.

Jam and Lewis took her under their wing, got to know her, and familiarized themselves with her world. Then they wrote songs together, based on different aspects of Janet’s life. “Jimmy and I rode around Minneapolis and we talked about my life and what I had gone through,” she said. “We talked about everything and they made me feel open enough and comfortable enough to speak to them about everything, because I was kind of withdrawn. My family were not able to trust people so we grew up very sheltered and were very private. So Jimmy and Terry allowed me to open up to them and express myself.”

Finding her voice

Amazingly, Control yielded four more US R&B chart-toppers: the funked-up, attitude-heavy “Nasty”; the assertive title song, which was Janet’s declaration of independence; the sweet ballad “Let’s Wait Awhile,” which showed her sensuous side; and the electro-influenced dance groove “The Pleasure Principle.” Another single, the joyously upbeat “When I Think Of You,” surprisingly stalled at No.3 on the US R&B chart, but became her first mainstream chart-topper. Meanwhile, the slow ballad “Funny How Time Flies” wasn’t released as a single but quickly became a fan favorite spawning a swathe of smooth jazz cover versions.

Reflecting on her timely collaboration with Jam and Lewis, Janet Jackson was grateful for their input and building her confidence as an artist. “They allowed me to grow, they allowed me to blossom,” she said. “There are producers that would say: wait a minute, this is way too much. But they were like, no, if this is what she wants to do and this is the way she wants to express herself, let her do it.”

With Control, Janet Jackson made an album that truly reflected her as a person. Despite its title, it was the album that finally set her free.

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There’s no arguing that the 90s is the golden age of R&B. The best 90s R&B songs still sound fresh, and their influence can be felt in the crop of modern R&B stars who are pushing the genre forward.

From floor-filling anthems to outpourings of emotion – and all soulful points in between – each of the 75 tracks in our list of the best 90s R&B songs represents a defining moment in the genre, and in the careers of the artists who sang them.

75: After 7 – Til You Do Me Right

The Indianapolis-based trio was one of the most versatile groups of 90s R&B, from vintage soul to New Jack Swing and slick ballads they could do it all. After breaking out in 1989 with “Can’t Stop” they teamed up again with Babyface and L.A.Reid on their third album Reflections the most essential slow dance ballad, “‘Til You Do Me Right.

74: Dru Hill – How Deep Is Your Love

Not to be confused with the Bee Gees’ classic, this song instead is all about Dru Hill’s sexual prowess. This single also helped the group blow up when it appeared on their sophomore album Enter The Dru. It had all the hallmarks of the classic Dru Hill sound: impeccable harmonies, staccato production flairs, and Sisqo’s unmistakable vocal runs.

73: Immature – Never Lie

Don’t let the name fool you, Immature were wise beyond their adolescent ages, making grown R&B jams to slow drag to. “Never Lie” was off the group’s second album, Playtime is Over, which saw the group catering to an older audience than their usual teenaged fanbase, and hitting No.5 on the Billboard Hot 100.

72: Faith Evans – Soon As I Get Home

The widow of Notorious B.I.G., Faith Evans’s musical talent is often overshadowed by her personal life. But the church-choir-bred vocalist had a talent that was leaps and bounds beyond many of her peers. Honeyed and at once yearning and comforting, Evans’ velvet voice skims over this wistful romantic ballad with depth and precision.

71: Silk – Freak Me

The 90s were an especially freaky time for R&B – see: “Freak Like Me,” “Freek’n’ You” – and Silk add their own sensual single to the mix with their No.1 hit, “Freak Me.” Under the guidance of New Jack Swing vocalist/producer Keith Sweat, Silk couched their more lustful lyrics in gorgeous vocals, so you had to go back and read the lyrics before blushing.

70: Sybil – Make It Easy On Me

Coming off of the smash success of her cover of Dionne Warwick’s “Don’t Make Me Over,” the former disco diva embraced a more R&B sound on her second album Sybilization featuring the upbeat breakup song, “Make It Easy On Me.” Despite it being about a relationship that has run its course, the infectious dance-pop production makes it sound like she was better off anyway.

69: Neneh Cherry – Woman

This heavy soul song is a response to James Brown’s 1966 hit “This Is a Man’s World”. Neneh Cherry discusses the strength, resilience, and power that transcends and remains despite everything this woman has been put through. By the end of the song, it is clear that this is a woman’s world.

68: Paula Abdul: Rush Rush

This album was the swan song of Paula Abdul’s career as a singer. This ballad is lush and heavy on the strings and the music video featuring Keanu Reeves was inspired by Rebel Without a Cause.

67: Brian McKnight – Back At One

Apparently, Brian McKnight came up with the lyrics to this song while he was reading an instruction manual on how to put together his stereo system. If these steps to get your woman to fall in love with you fail, start back at one.

66: Johnny Gill – My, My, My

Another Babyface produced hit, this sultry tune won the Soul Train Music Award for Best Male R&B, Soul single and Johnny Gill proved that like Bobby Brown and Bell Biv Devoe, he too could be a success on his own, outside of New Edition.

65: Somethin’ For The People – My Love Is The Shhh!

One of the more unsung 90s R&B cuts, “My Love Is The Shhh!” by West Coast Trio Somethin’ For The People was another perfect blend of hip-hop soul and enlisted the talents of fellow contemporary R&B group Trina & Tamara. While Somethin’ For The People never blew up, their penned hits for Brandy and En Vogue did.

64: Sounds of Blackness – Optimistic

Written and produced by the legendary Jimmy Jam and Terry Lewis, this inspiring gospel/R&B song reminds listeners to, “keep your head up to the sky” and “to hold on to your dreams.” In 1991, this song went all the way to No.3 on the Hot R&B/Hip Hop songs chart.

63: Deborah Cox: Nobody’s Supposed To Be Here

After suffering through heartache Deborah Cox is surprised to find a new love possessing the key to her heart. The unlikely, gospel-inflected hit helped establish Cox as a household diva of the 90s and eventually became a gay anthem, thanks to a remix by Hex Hector.

62: Tamia – So Into You

This feel-good love song came out in 1998 and remains Tamia’s most recognizable hit. Over the years the song has been covered by Brandy, Fabolous (with Tamia singing the hook), and in 2015 Childish Gambino.

61: K-Ci & JoJo – All My Life

Putting their “Freek’n You” of days of Jodeci behind them, brothers K-Ci and JoJo Hailey returned to their traditional roots with their side project, Love Always, consisting of more wholesome R&B fare. When JoJo penned “All My Life” for his daughter, he had no idea it would become the duo’s longest-running number-one single of their career and one of the most popular wedding songs of all time.

60: Sade – No Ordinary Love

Sade is the epitome of sensuality. This song was her first release in the 90s and she gifts us with a seven-minute slow burn of a tumultuous love affair that cannot be sustained.

59: Babyface – When Can I See You

This is by far Babyface’s most successful and most recognizable song. With Babyface broken-hearted and unable to move on from his love, hopefully, the answer was “soon.”

58: All-4-One – I Swear

Maybe you put this on a mixtape to your middle school crush or swayed to it at a dance, but this ballad is as serious as it gets. It was originally written for country music singer John Michael Montgomery but All-4-One made it a No.1 hit and won a Grammy for best pop performance in 1995.

57: Whitney Houston – Exhale (Shoop Shoop)

After the success of the Boomerang Soundtrack, Whitney Houston returned with this song off of the Waiting to Exhale soundtrack. The song’s message about getting back up again after experiencing the anguish of heartache still hits.

56. New Edition – I’m Still In Love

Having perfected the blueprint for early 90s R&B songs, New Edition proved they were no longer just a fresh-faced boy band and were all grown up with “I’m Still In Love.” The second single from the fittingly titled Home Again album saw the group reunite with frontman Bobby Brown along with their veteran production team of Jimmy Jam and Terry Lewis to create a sensual jam that stormed the charts.

55: Dionne Farris – Hopeless

Coming off of the success of Arrested Development’s “Tennessee” and her own, “I Know,” Dionne Farris’ “Hopeless” was then featured on the iconic Love Jones Soundtrack. This timeless song about a hopeless romantic who remains optimistic is an absolute gem.

54: Blaque – Bring It All To Me

One of the essential Y2K R&B cuts, Blaque learned a lot about making sing-a-long jams under the tutelage of Lisa “Left Eye” Lopes of TLC. And thanks to the remix, you get to hear J.C. Chasez from N’Sync sing about his “Timbs, baggy jeans and thug appeal.”

53: INOJ – Love You Down

This extremely upbeat cover of Ready For The World’s 1986 tune took the airwaves by storm 11 years later in 1997. INOJ’s rework of the song and her cover of Cyndi Lauper’s “Time After Time”, was less a slow jam or ballad than a song to be blasted at your cardio funk class.

52: Queen Latifah – Weekend Love

Queen Latifah takes you on a playful ride into the sun, fun, and freedom of the weekend. She leaves the rapping duties to Jamaican emcee Tony Rebel and blesses us with her vocals.

51: Nuttin’ Nyce – Down 4 Whateva

Featured on the Low Down Dirty Shame soundtrack, Nuttin’ Nyce struts their stuff with this heavily sampled hit. Blending West Coast hip-hop flavor with powerful vocals, this song was made for cruisin’ the streets.

50: Mokenstef – He’s Mine

Not your typical R&B jam, Mokenstef – a combined moniker of the group’s members Mo (Monifa), Ken (Kenya), Stef (Stefanie) – didn’t mince words when they tell it “Azz Izz.” “He might be doing you but he’s thinking about me” a very open-minded girlfriend talking to her man’s mistress letting her know that, “you might have had him once” but that she’s, “got him all the time.” The swaggering cut sways back and forth in your brain like Aaliyah.

49: Monica – Don’t Take It Personal (Just One Of Dem Days)

Monica was only 15 when she released this R&B classic. Featuring a sample of LL Cool J’s “Back Seat,” this hip-hop-influenced R&B song struck a chord with teens everywhere.

48: Total: Trippin

Total is by far one of the most underrated R&B groups of the 90s. Written by and featuring Missy Elliott, this sexy song about losing your cool over your boo is catchy and bouncy. “Trippin” would become the biggest hit of their career after going to No.7 on the Billboard Hot 100.

47: 702 – Where My Girls At

Produced by Missy Elliot and Key Beats, the biggest hit for 702 asks for backup in the form of girl power. After realizing that another woman is scheming on taking her man, 702 summons all the ladies in the house to put one hand up to this hip-hop ladies’ anthem.

46: Destiny’s Child – Say My Name

Before Bey went solo there was Destiny’s Child. Produced by Rodney “Darkchild” Jerkins, this song demands to know if the man they love is cheating. This was Destiny’s Child’s breakthrough song, the one that put them on the map.

45: Brownstone – If You Love Me

An essential anthem from the cannon of R&B classics told from the perspective of “the other woman,” Brownstone gives their man an ultimatum to “act like you’re mine in the light and the dark.” The song begins as a ballad before it eventually breaks out into a swaggering New Jack Swing strut.

44: Charles & Eddie – Would I Lie To You?

Charles (Pettigrew) and Eddie (Chacon) met on a New York City subway where Charles saw Eddie holding a Marvin Gaye album and struck up a conversation. The rest is history, along with this 60s-soul-inspired classic. The duo remained something of a one-hit-wonder stateside, but was a constant fixture on the UK charts from 1992 and 1995.

43: Des’ree – You Gotta Be

“You Gotta Be” was both an inspiring, affirmative anthem and one of the most infectious singles on the radio, thanks to its fusion of jazz and soul. The UK singer’s biggest hit and personal mantra was inescapable in 1994, along with the striking black-and-white video that became the most played music video on VH1.

42: Tevin Campbell – Can We Talk

Tevin Campbell was everyone who ever tried to find the courage to talk to their crush. “Can We Talk” was all about the angst of teenage love, longing and words left unsaid.

41: Hi-Five – I Like The Way (The Kissing Game)

Another essential New Jack Swing cut, Hi-Five’s “I Like The Way” was on the more wholesome side of 90s R&B, turning singer Tony Thompson into teen heartthrob material overnight. The song shot its way to the top of the Billboard Hot 100 thanks to the Midas touch of Teddy Riley.

40: Joe Public – Live and Learn

Another New Jack Swing success, this song samples Steely Dan, Parliament, Sly & the Family Stone, and the J.B.’s, among others. Beyond the head-nodding production, the lyrics impart some sage advice.

39: Portrait – Here We Go Again!

A New Jack Swing tune about going another round with your jealous significant other never sounded so good. The song samples the irresistible beat to Digital Underground’s “The Humpty Dance” and Public Enemy’s “Bring the Noise.”

38: Shai – If I Ever Fall In Love

Shai’s a cappella harmonies were unmatched, which is probably why this song can still raise the hairs on the back of your neck.

37: Keith Sweat – Twisted

One of the most unforgettable videos of the decade, Keith Sweat’s “Twisted” was a three-minute murder-mystery-romance that helped to launch the second wave of the R&B impresario’s career. A runaway hit, “Twisted” is infectious and danceable, and Sweat’s distinctive vocal style makes it a song only he could have pulled off.

36: Erykah Badu – On & On

The breakout hit and first single of her debut album, Baduizm, “On & On” track confounded critics even as it delighted them. Is she hip-hop? Is she R&B? Is she soul? Badu answered by being all that and more. The jazz-inflected beat on “On & On” lopes along, peppered with sly, self-aware lyrics that are as humorous as they are timely. This track was the very first taste of what was to come from an artist who has smashed through every musical boundary she’s ever encountered.

35: Xscape – Just Kickin It

“Just Kickin It’ was the ultimate “around-the-way girl” anthem by Southern R&B outfit Xscape. Discovered by Jermaine Dupri for his So So Def label, Xscape was the “hip-hop version of En Vogue,” said Dupri, which summed up their tomboy swagger.

34: Groove Theory – Tell Me

This smooth song built its bassline around 1983’s “All Night Long” by Rick James’s protege group, The Mary Jane Girls. With that as its foundation, lead singer Amel Larrieux’s honeyed harmonies with bandmate Bryc Wilson resonated with radio listeners around the world.

33: PM Dawn – I’d Die Without You

First appearing on 1992’s Boomerang Soundtrack, this beautifully crafted song feels reminiscent of something Sade may have recorded and remains one of PM Dawn’s biggest hits.

32: D’Angelo – Brown Sugar

Before the bared abs of Voodoo was Brown Sugar. The most popular track off D’Angelo’s album of the same name feels as timeless today as it did when it was released in 1995, sizzling with lo-fi sexiness, deep funk, and the freshness that D’Angelo would come to be known for.

31: Janet Jackson – That’s The Way Love Goes

There is a Janet Jackson for all seasons: there’s nasty Janet, drill sergeant Janet and then there’s come-hither Janet. The lead single off her 1993 album, Janet, “That’s The Way Love Goes” finds Jackson letting her hair down. A lyrical and musical pivot, it showed the world that Miss Jackson was all grown up. Built around a sample from James Brown’s “Papa Don’t Take No Mess,” the single locks into a smooth downtempo groove and burns all night.

30: Lauryn Hill: Ex-Factor

Lauryn Hill initially penned “Ex-Factor” for another group but felt it was too personal to give away. This beautiful, heart-wrenching, breakup song was on repeat on many a Discman due to its relatability and stirring vocal performance.

29: Aaliyah – One In A Million

“One In A Million’ was the fruit of Aaliyah’s first collaboration with Missy Elliott and Timbaland. A club ballad that fused elements of funk, electronica, and trip-hop, and put Aaliyah’s ethereal vocals on full display, it was the perfect distillation of all the pervasive sounds of the era. As one of the best 90s R&B songs, it would turn Aaliyah into the decade’s patron saint of R&B.

28: Selena – Dreaming Of You

“Dreaming Of You” was the ballad of the mid-90s, Selena tapped into the unbridled longing that comes with every adolescent crush. As the lead single from her 1995 posthumous album, it was clear Selena was meant to be a huge star.

27: Brandy & Monica – The Boy Is Mine

Two R&B divas are better than one, and “The Boy Is Mine” combined the powerhouse vocal stylings of Brandy and Monica. The iconic duet completely dominated the charts (and culture) the summer of 1998, topping the Billboard Hot 100 for 13 weeks, selling over 3 million copies, and earning them both a Grammy Award.

26: Soul IV Real – Candy Rain

R&B meets bubblegum pop in Soul IV Real’s bouncy debut single “Candy Rain.” Powered by the youthful voice of the youngest brother Jason “Jase” Dalyrimple of their family band, the single still slapped thanks to production by their mentor and Uptown labelmate Heavy D.

25: Usher – You Make Me Wanna

It may have been co-written by Jermaine Dupri, but this track is classic Usher. The R&B crooner agonizes over the object of his affection over a smooth, slinky beat accompanied by hi-hat instrumentals that feature so prominently in his catalog.

24: Jodeci – Freek’n You

With opening lyrics no less frank than “Every time I close my eyes/I wake up feelin’ so horny,” Jodeci cemented their legacy as one of the 90s’ most influential R&B groups. With a seductive beat, “Freek’n You” was a chart-topper that contains possibly the only extant example of a vocoder-sounding erotic.

23: H-Town – Knockin Da Boots

90s R&B was the golden age for creative sexual innuendo and no group embraced it more than Houston’s H-Town and their hit single “Knockin Da Boots,” produced by Luther “Uncle Luke” Campbell from the explicit rap group 2 Live Crew.

22: Next – Too Close

According to Next crew, they wrote this song after a woman on the dance floor purposely backed up on one of the guys to “see what they’re working with” and based on that, the dancing either continued or she’s on to the NEXT.

21: En Vogue – My Lovin’ (You’re Never Gonna Get It)

As with most arts, sampling is inexpertly done more often than not. But the sample on En Vogue’s most iconic track is an example of how to do it right. Poppy, funky and soulful, En Vogue belt the song out over a few bars from James Brown’s “The Payback.” Factor in the unforgettable dancefloor-filling breakdown and it’s no wonder that “My Lovin’” stayed in the US Top 10 for 13 weeks.

20: Monifah – Touch It

One of the first artists signed to Uptown Records, Monifah knew she had to dial up the sex appeal on her sophomore album Mo’hogany. Built around a sample of Laid Back’s Euro-club hit “White Horse,” “Touch It” lays the innuendo on thick and defies you not to bounce.

19: Brandy – I Wanna Be Down

With its opening lyrics, “I would like to get to know if I could be… the kind of girl that you could be down for,” Brandy’s teenaged tentativeness ushered in a new era of R&B women. A singer with sophistication, playfulness, and style, Brandy’s clever and adorably vulnerable lyrics were backed by a punchy, danceable beat to give us the decade’s anthem for modern adolescent romance.

18: Toni Braxton – You’re Makin’ Me High

A hot song with an equally hot video, Toni Braxton’s runaway No.1 from her sophomore album was the hit of the summer of ’96, and more than earns its place among the best 90s R&B songs. Rumored to be about everything from weed to masturbation, the suggestive lyrics were cleverly buried under a poppy, danceable, uptempo beat that borrowed from the burgeoning electronica movement.

17: Boyz II Men – On Bended Knee

During the 90s, it felt like Boyz II Men released a new hit every week. Even at that prolific rate, “On Bended Knee” stands out as a deliciously melodramatic cut above the rest. It’s the perfect cocktail of the four Philly balladeers’ vocal styles: drama, wistfulness, longing, and a chorus that’s still belted out of karaoke rooms from coast to coast.

16: Adina Howard – Freak Like Me

“Freak Like Me” not only served as Adina Howard’s sex-positive debut but paved the way for fellow female R&B vocalist to own their sexuality on record. It was one of the first 90s R&B songs where a woman talked unapologetically about her desires, plus the beat thumps to this day.

15: TLC – Waterfalls

This was by far the biggest song off TLC’s seminal CrazySexyCool album. TLC addresses social issues over smooth horns and sharp high hats as Left Eye delivers one of her best (and sadly, last) rhymes of her career.

14: SWV And Missy Elliott – Can We?

Missy Elliott and Timbaland unequivocally ruled control rooms in the 90s, and this track with R&B darlings SWV is a perfect example of why. Timbaland’s haunting production style is layered and nuanced here. Has he touched anything that didn’t turn to gold? Missy’s slick, rapid-fire rhyming stays firmly grounded in the beat, while SWV’s lyrics soar above it.

13: Maxwell – Ascension (Don’t Ever Wonder)

Released at a time when sample-heavy, hip-hop soul ruled the airwaves, Maxwell’s grooving debut and soulful crooning sounded more like the source material than a sample ever could, and remains one of the classic 90s R&B records of all time.

12: Blackstreet: No Diggity

1996 was a good year for R&B – especially for Blackstreet. Teddy Riley had initially offered “No Diggity” to the group Guy, but they rejected it. Blackstreet balked at first (they apparently thought the title was corny) but Riley convinced them of its brilliance and the group ultimately embraced the song. The single which famously samples the piano chords from Bill Withers’ “Grandma’s Hands,” features a verse by Dr. Dre, who ultimately produced the track, turning out a No.1 hit that became the group’s defining anthem.

11: Jade – Don’t Walk Away

This catchy New Jack Swing tune bumps thanks to the classic Kool & the Gang sample. Part R&B jam with a hip-hop feel, the ladies of Jade lace this track with their sweet harmonies.

10: Color Me Badd – I Wanna Sex You Up

Dr. Freeze, who was also responsible for BBD’s “Poison,” produced this sultry track which was featured on the 1991 New Jack City soundtrack. These sensitive singers get right to the point by the chorus sampling Slick Rick “to the heart, tick-tock, you don’t stop.”

9: Ghost Town DJs – My Boo

This Miami bass-inspired one-hit wonder with its smooth harmonies is one of So So Def’s finest contributions. A fixture of any self-respecting pool party or BBQ, the Atlanta classic crops back up on the charts every few years, evidence of its timeless appeal.

8: Mary J. Blige – Real Love

Taken from her debut album, What’s The 411?, Mary J Blige’s very first Top 10 hit is an example of using a sample to create something original. Plucking sonic inspiration from Audio Two’s “Top Billin’,” the opening bars of “Real Love” have become synonymous with Blige and are among the most identifiable in the history of R&B. With this track alone, the soon-to-be queen of hip-hop soul and 90s R&B had already earned her crown.

7: Tony! Toni! Toné! – Feels Good

A fusion of R&B, pop, and a classic New Jack Swing beat, Raphael Saadiq and his bandmates, brother D’Wayne Wiggins and cousin Timothy Christian Riley, hit pay dirt with this party-starting anthem that landed them in the Top 10 for the first time. The song embodied all the elements that defined that era and remains one of the best 90s R&B songs that should be played “as frequently as possible.”

6: Mark Morrison – Return Of The Mack

Mark Morrison declared to the world that he was back after recovering from a cheating girlfriend. Even though she lied, this Mack is doing just fine. Although some of his wording is a touch indecipherable, his success remained the sweetest revenge.

5: Zhané Hey: Mr. DJ

More than 20 years after its initial release, “It’s Friday night and the weekend’s here, I need to unwind” remain some of the most resonant words in R&B history. With a swinging beat and soft, lush production, Zhané’s “Hey Mr. DJ,” from the duo’s debut album, Pronounced Jah-Nay, is the perfect representation of R&B’s prime objective: to be the sonic expression of the soul of the everyman and everywoman.

4: Montell Jordan: This Is How We Do It

This is the ultimate party starter that has stood the test of time. “It’s Friday niiight and I feel alright!,” Montell Jordan sang over a sampled loop of Slick Rick’s “Children’s Story.” The true universality of the song’s message made it a No.1 hit and used in everything from film soundtracks to teacher strikes.

3: Ginuwine – Pony

Not to be outdone, Ginuwine’s sonic love letter to lady-on-top has what is quite possibly the most unmistakable beat in R&B history, along with the least subtle metaphor ever written. The syncopated rhythm (courtesy of Timbaland) and that unforgettable rattle helped Ginuwine’s debut rocket right to the No.1 spot.

2: Mariah Carey – Fantasy

Choosing the best R&B jam from the Mariah Carey cannon is like picking your favorite child, the woman has had No.1 hits every decade since she hit her first falsetto note, but “Fantasy” combines all of the elements of Mimi. Built around a sample of Tom Tom Club’s “Genius of Love,” it’s pop perfection meets R&B attitude, kicking off with vocal runs before hitting its groove. And the Bad Boy produced ODB-remix would become the blueprint for future pop hip-hop collabs.

1: Bell Biv Devoe: Poison

Once you hear the first snare of this jam, people on the dance floor automatically start doing the running man. Bell Biv Devoe features half of New Edition and is one of the first examples of blending R&B and hip-hop pre-Jodeci. This New Jack Swing classic reminds us all to “never trust a big butt and a smile.” Words to live by.

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I cannot recall when I first heard the name Ed Sullivan, but it certainly had to have been when I was a ghetto youth coming of age in the 1970s and 1980s. I initially connected his name with music superstars Elvis Presley and The Beatles, and their now legendary appearances on his variety show. I was intrigued by how he introduced musical guests, his mightily distinctive diction, his genuinely low-key demeanor. But I had no clue, truly, who the man was, why he was such a major force in entertainment, and why for so long, until after I reached adulthood.

That recognition likely began when I studied Black history and Black culture while in college, and in the years that followed when I became a journalist, particularly as a documentarian of music and other art forms. And by the time I was hired to be a senior writer at Quincy Jones’ Vibe magazine in the 1990s, I found myself perpetually scanning “The Ed Sullivan Show” for footage after footage of Black performers like The Jackson 5, like Mahalia Jackson, like the legit who’s who of Black genius in song, dance, film, theater, and comedy. It was almost as if Ed Sullivan had been intentionally curating Black history on television, knowing that Black lives not only mattered then, but would matter to those to come, like me.

Watch all the latest archival videos from The Ed Sullivan Show on the program’s official YouTube channel.

Indeed, it was somewhere between my Vibe years and the past decade or so that I learned how invested Mr. Sullivan was in equality. Perhaps it was because, as a young man, he was a serious and great athlete, and had encountered Black folks on the sporting field as gifted as he, and it left an impression – one that taught him not to view any people as inferior, as was commonly believed in Jim Crow America, just because of the color of their skin. Perhaps it was because he was Irish and knew there was a time in this nation where there were loud proclamations that the Irish were considered the absolute bottom of the immigrant barrel. Perhaps it was because the love of his life, his wife Sylvia, was Jewish, and he saw first-hand the anti-Semitism those like her endured.

These and other factors are likely why The Ed Sullivan Show was converted into the performance arm of the Civil Rights Movement. Because he was such an icon and such an influencer, he was able to have Black artists in that theater when they were often not welcomed nor wanted elsewhere.

How else would you explain The Temptations and The Supremes doing their massive pop hits in that hallowed circle, accorded the same treatment as White musical innovators? And, yes, how else could Motown have become “the sound of young America” without allies and accomplices like Ed Sullivan?

How else do you explain Mr. Sullivan, a close friend of Bill “Bojangles” Robinson, the tap dancer who was once the biggest Black star in Hollywood, arranging the funeral service for a Black man who had the sad misfortune of dying broke, and doing so in a manner that suggested, strongly, this Black man was worthy of a grand send-off?

How else would you explain Mr. Sullivan, a White man, walking matter-of-factly into the yellowed and hateful teeth of racism by kissing Pearl Bailey on the cheek, or shaking the hand of Nat “King” Cole, on his TV show, knowing such gestures would savagely anger many White viewers, especially those in the American South who believed, without apology, in “For Whites Only” and “For Coloreds Only” in every way conceivable?

For sure, we know that The Ed Sullivan Show was the longest-running variety program in American TV history. We know that Mr. Sullivan became a star as big as the biggest stars he had on that program. But we also know that the Civil Rights era, roughly 1955 to 1968 – from the murder of Emmett Till and the Montgomery Bus Boycott to the assassination of Dr. King – means that Ed Sullivan had a front-row seat to the most dramatic upheavals sweeping America.

Here he was, someone who had spent considerable time digesting the Black talent in Harlem and via the “chitlin’ circuit,” with this gargantuan platform before there was social media, before there was cable or streaming, before there were all-music outlets like MTV, quite literally broadcasting Black history into the living rooms of everyday Americans year after year, from the World War II generation to the Baby Boomers, from nonviolent sit-ins and freedom rides to city after city burning in rebellion.

This is why I believe Mr. Sullivan did two things of great significance near the end of his remarkable television run. When he learned that Rahsaan Roland Kirk, the jazz multi-instrumentalist, was challenging the power structure to have more jazz on the airwaves, Mr. Sullivan did not do what others were doing: shucking and jiving and avoiding. He gave Mr. Kirk a slot with his makeshift band that included jazz giant Charles Mingus, and it remains one of the most searing and surreal mini-concerts ever seen on TV.

But history is not history if it does not also acknowledge the traumatic that happened in real-time. Two years after the Reverend Doctor Martin Luther King, Jr. was tragically gunned down in Memphis, America remained a divided and burning house. Yet there was a regal and soft-spoken Coretta Scott King, MLK’s widow, in that Sullivan moment, introducing clips from two of her late husband’s most famous speeches, and declaring the kind of America it needed to be. An emotionally raw Ed Sullivan greets Mrs. King at the end, kisses her on the cheek and grabs her hand, a fearless middle finger to anyone who believed, and still believes, that White people and Black people should not even touch each other, that our histories are not intertwined, when they are.

Without question, Ed Sullivan could have lived a life awash in White male privilege and power and ignored what was happening around him. Instead, he chose a path of purpose, of substance, not knowing that there would be, say, an African American like me, in a completely different century, who would religiously watch his show on YouTube and elsewhere, and see not just my people and our whole selves, with great pride and dignity, but also see what is possible if history is inextricably linked to a sense of humanity, to a great love for all.

Watch all the latest archival videos from The Ed Sullivan Show on the program’s official YouTube channel.

Kevin Powell is a poet, journalist, human and civil rights activist, filmmaker, and the author of 15 books, including the poetry collection Grocery Shopping with My Mother. He is also the writer of a forthcoming biography of Tupac Shakur. Kevin lives and thrives in Brooklyn, New York.

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