Graphic by Callum Abbott, photos via Getty Images

The 53 Best R&B Songs of the ’90s

From the throwback thump of Erykah Badu and D’Angelo to the freaky futurism of Aaliyah and Ginuwine to the unbridled horniness of Jodeci and Janet Jackson

In the 1990s, R&B underwent a sea change. Though the songwriting was still steeped in traditional romance and courtship, the influence of hip-hop brought about edgier production styles, raunchier attitudes, and new commercial peaks. Hardcore crooning and freaky ballads were everywhere, alongside vocally deft girl groups and harmonized ensembles who took begging and pleading to another level. At the same time that the genre was extending its reach, its sound was evolving too, from Teddy Riley’s danceable percussion and neo-soul’s live instrumentation to Timbaland and Missy Elliott’s gravity-defying experimentation.

The following list, presented alphabetically by artist, includes R&B tracks featured on our 250 Best Songs of the 1990s, plus 21 more that are integral to the genre’s commercial and artistic expansion.

Read Pitchfork’s list of the best songs of the 1990s here and best albums of the 1990s here, and check out our full ’90s package here.

Bad Boy

112: “Only You (Bad Boy Remix)” [ft. The Notorious B.I.G. and Mase] (1996)

The four members of 112 met in their Atlanta high school’s choir and saw themselves as conventional crooners, but Puff Daddy had a different vision. Hip-hop and R&B were increasingly colliding, thanks to producers like Bad Boy’s in-house team, the Hitmen Squad, who were spinning lesser-known soul records into new-school club classics. Released amid an explosion of Bad Boy hits, 112’s debut single, “Only You,” embodies everything good about the shiny suit era. On this rework, Hitman producer Stevie J bends a sample of George McCrae’s 1974 single “I Get Lifted” into a springy remix with beaucoup swagger, matching frontman Slim Scandrick’s sultry notes. The song is about being stuck in a loop with a love that’s uncertain, but the most memorable thing about it is the bounce. –Clover Hope

Listen: 112, “Only You (Bad Boy Remix)” [ft. The Notorious B.I.G. and Mase]

Blackground / Atlantic

Aaliyah: “Are You That Somebody?” (1998)

“Are You That Somebody?” was the song that consolidated Aaliyah’s image as a refined and unapologetic streetwise princess, supplanting the more traditional R&B sound of her work with R. Kelly in favor of something that nudged toward hip-hop soul. The material Timbaland and Missy Elliott created for the singer didn’t require her to scream or over-embellish, but rather forced you to listen harder: Aaliyah’s vocals grew more compelling the softer and more subtle they became. She could grab attention simply by being unusually calm, the gleaming center of a rhythm track that telegraphed emotional chaos in its fits and starts.

Learning from catastrophic sample lawsuits against De La Soul in 1989 and Biz Markie in 1991, Timbaland became one of the first producers to create signature hip-hop loops out of obscure sound-effect records and found noises. The baby gurgles that punctuate the song’s stuttering tango are first ridden by Tim’s gravelly vocal affirmations, then by Aaliyah’s hushed, reedy croon. The hybridized sound—intentionally odd, jittery tempos, backed by syncopated commentary—was groundbreaking and reflective of something more: the building of a persona around Aaliyah with an even greater mystique than that Jimmy Jam and Terry Lewis had created for Janet Jackson in the years prior. –Carol Cooper

Listen: Aaliyah, “Are You That Somebody?”

Blackground / Atlantic

Aaliyah: “One in a Million” (1996)

Skittering percussion and squirming sub-bass have dominated rap and pop production for so long now it’s easy to forget that when Aaliyah’s “One in a Million’’ debuted in 1996, Timbaland’s style had yet to gain a foothold on radio or MTV. Just four seconds into the song you hear it, though: the rapid flicker of hi-hats, the element that always made his early work sound as if it were a stuttering transmission from the future. Every time it happens in “One in a Million” it’s like time mutates, lurching forward and then snapping back on itself like a rubbery cartoon character. In this case it mirrors the song’s subject: falling in love with someone so hard that you feel the continual pull of their gravity. And no voice navigated these thickets of drum patterns more capably than Aaliyah’s; she rides the currents of the undulating groove as if she were piloting a hang glider through them. –Brad Nelson

Listen: Aaliyah, “One in a Million”

East West / Lola Waxx

Adina Howard: “Freak Like Me” (1995)

R&B singer Adina Howard’s biggest hit serves as a member’s pledge for Club Freak: a place where a woman can proudly self-describe as a “dog” and live shame-free in her liberated sexuality. Subverting peacocking rap masculinity over a breezy invocation of G-Funk, Adina leans all the way back in the driver’s seat, refusing to pull out her wallet for any man. The song samples Sly Stone and Bootsy Collins, but its finest flip occurs when Howard transforms the squeaked-out Mary Jane Girls sample from LL Cool J’s girlfriend-wishlist “Around the Way Girl” into an expression of her own needs: “I got you shook up on your knees.” Over the years, “Freak Like Me” has been famously covered by Sugababes and interpolated by Megan Thee Stallion and SZA, continuing to stomp all over whatever’s left of the idea of ladylike decorum. –Claire Lobenfeld

Listen: Adina Howard, “Freak Like Me”


Allure: “All Cried Out” [ft. 112] (1997)

“All Cried Out” was initially released in 1985 as a piano-tinged power ballad by freestyle icons Lisa Lisa & Cult Jam, characterized by weepy theatrics and huge AquaNetted bangs. Allure’s revival a little more than a decade later revealed what Lisa Velez’s voice, which was better suited to dance music, didn’t quite illustrate: In the hands of two profoundly raw quartets who could sing their faces off, “All Cried Out” is masterful storytelling, chronicling the pain of a breakup in heart-wrenching, minute-by-minute detail. Allure were fresh out of Manhattan’s famed LaGuardia performing arts high school, but they had the resonance and harmonies of a more mature group. With Bad Boy heartthrobs 112 playing foil on the second verse, the whole affair is a devastating emotional bonfire, one that meets the moment for your messiest, most melodramatic goodbyes. As they sing in beautiful misery towards the end, “Don’t you know my tears will cause an inferrrnoooo?” –Julianne Escobedo Shepherd

Listen: Allure, “All Cried Out” [ft. 112]


Bell Biv DeVoe: “Poison” (1990)

Before “Poison” rocketed them to superstardom, Ricky Bell, Michael Bivins, and Ronnie DeVoe were pretty much only known as “the other guys in New Edition.” That gave them the freedom to try out a risky new sound, a groundbreaking blend of R&B and hip-hop that framed the group’s vocal harmonies in gritty production. At the time, the casual misogyny of the song’s raps were the clearest sign that these guys were done wooing “Candy Girl”s; thirty years later, it’s hard to find anything smooth about lines like “the low pro ho she’ll be cut like an afro.” But that opening dirty snare roll, now as iconic as “Be My Baby,” still finds a way to fill any wedding or bar mitzvah dance floor, regardless. –Jessica Suarez

Listen: Bell Biv DeVoe, “Poison”


Boyz II Men: “Motownphilly” (1991)

Was life really ever as earnest and pure as Boyz II Men’s “Motownphilly” music video made it out to be? In 1991, when the fledgling Philly group released its first single, it was all youthful exuberance spilling out in oversized pink blazers, matching bow ties, and snazzy horn riffs. (Also: If Tik Tok teens haven’t studied this choreography yet, they are missing out.) Michael Bivins of New Edition and Bell Biv DeVoe appeared on the track, which features classic soul harmonies over a new jack swing beat, as well as a totally gratuitous doo-wop showcase at the end. Not too hard and not too soft, the song ushered in the decade of copycat (and largely whitewashed) boy bands that would follow. –Emma Carmichael

Listen: Boyz II Men, “Motownphilly”


Brandy: “I Wanna Be Down” (1994)

The same year Brandy released this breakout hit, a 15-year-old Aaliyah was emerging as the voice for cool girls. In contrast, Brandy was the precocious role model who signed a major label deal at 14, around the same time she played an acerbic teenager on the network sitcom Thea. As a singer, she stuck to a more innocuous brand of R&B than her peers, peddling songs about crushes and coming-of-age sensations, powered by hope and naïveté. “I Wanna Be Down” thumps sweetly, like the heart of an adolescent in love. Though Brandy would increasingly break free from her early goody-two-shoes reputation, this song is the sound of a girl uncorrupted. –Clover Hope

Listen: Brandy, “I Wanna Be Down”


Brandy / Monica: “The Boy Is Mine” (1998)

Brandy laid down her feathery sweet vocals in California, while Monica recorded her tough and soulful melodies in Atlanta. Some have said it’s because their voices weren’t meshing; others have said it’s because they couldn’t stand each other. That they’ve only sung the soap opera-ready R&B classic once together live—on that same night Monica punched Brandy in the face—is reason enough to go with the latter. “The Boy Is Mine” has a simple driving idea: Brandy and Monica have found out that they are dating the same man. It’s fiction, but as they trade stingy jabs, that line between reality and story is blurred, and the way Brandy airily coos “He said without me, he couldn’t make it” probably hurts more than any punch could. Rodney Jerkins’ beat is the perfect backdrop, a harp buildup that could heighten any melodrama and a shimmering and shaking feel that gives the song more edge than it already has. Neither Brandy or Monica outshine each other, as their voices line up like two puzzle pieces. It’s one of the great duets of our time, even if they couldn’t stand each other. –Alphonse Pierre

Listen: Brandy / Monica, “The Boy Is Mine”

MJJ / Epic

Brownstone: “If You Love Me” (1994)

While their male counterparts were breaking promises and pleading for forgiveness, Brownstone were among the plethora of girl groups on the other side of the conversation. “If You Love Me” is an open call to action; its blunt lyrics clearly state the narrator’s intentions (“Don’t want your body without your soul”) over sweeping vocals and polished harmonies. So much of R&B is about upholding an era’s traditional relationship boundaries, and the ’90s were lush with church-girl groups like Brownstone, who rivaled prominent acts like SWV and En Vogue, singing power ballads about refusing to settle. Here, they turn their simple needs into gospel. –Clover Hope

Listen: Brownstone, “If You Love Me”


D’Angelo: “Brown Sugar” (1995)

“Brown Sugar” is effortlessly cool: In the music video, D’Angelo struts into a dimly lit lounge, sits at the piano, and instantly busts out the sweetest serenade, with smoke from a joint still coming out of his mouth. If you told me that’s how he actually recorded the song, I would absolutely believe it.

In an era when much of the popular R&B singles had been inspired by Teddy Riley’s new jack swing slickness, D’Angelo’s debut hit was a slow-burner that felt beamed in from another universe. Inspired by icons like Marvin Gaye, Al Green, and Stevie Wonder, the Virginia-raised singer pulled from those retro roots while addings elements of hip-hop, helping to lay the foundation for neo-soul. The rap influence is in D’Angelo’s look—cornrows and baggy clothes—but also in the tinny drums programmed by A Tribe Called Quest’s Ali Shaheed Muhammad, which give the song an almost slow-mo bounce. Filtered through the singer’s honey-smooth falsetto and mystic allure, the past and present become seamlessly intertwined. –Alphonse Pierre

Listen: D’Angelo, “Brown Sugar”


Deborah Cox: “Nobody’s Supposed to Be Here” (1998)

Deborah Cox spent the first six months of her music career touring as a backup singer for Celine Dion, a crash course in how to make every note a spectacle. On her breakout hit, “Nobody’s Supposed to be Here,” the smallest shifts are mesmerizing—the jagged edge in her throat when she admits love has knocked her down, the way the vowel caves in when she sings the word “sad,” the shock of shriek that builds up as she belts the chorus. Gentle percussion and chimes swirl in the background, and the song winds around and around Cox’s circular thinking, as she spirals through dejection, hope, and refusal, all leading up to a cathartic key change. “I’m not supposed to care anymore,” she moans as the track trickles out, a final sigh before she gives in. –Dani Blum

Listen: Deborah Cox, “Nobody’s Supposed to Be Here”


Destiny’s Child: “Say My Name” (1999)

Nearly two decades before Beyoncé delivered Lemonade, her heart-wrenching opus on self-transformation and forgiveness in the wake of a partner’s infidelity, she led Destiny’s Child’s glossy, unflinching interrogation of an untrustworthy lover with “Say My Name.” Beyoncé’s staccato, kinetic delivery—which influenced R&B vocal cadences for years to come—is effortless and unrelenting, underscoring her assertion that she is not one to be played. The song is all bravado, and circles a request so elemental that it shouldn’t even have to be asked: to be remembered, and treated with care and respect by someone who loves you. That tension between the audacity of Destiny Child’s performance and the vulnerability of their titular ask imbues the song with an incomparable poignancy. –Vrinda Jagota

Listen: Destiny’s Child, “Say My Name”


En Vogue: “Free Your Mind” (1992)

Appearing on a genre-fluid album laced with doo-wop-like jams like “My Lovin’ (You’re Never Gonna Get It)” and sensual classics like “Giving Him Something He Can Feel,” En Vogue’s “Free Your Mind” took us to rock as thrashing metal guitar riffs layered with keyboards, the group’s signature harmony, and a message of gender and racial unity. “It doesn’t mean that I’m a prostitute, no, no,” these curvaceous Black femmes in thigh-high boots wanted us to know—a radical message at a time when feminism was all but declared dead and a war on women was underway. Slut-shaming and moral judgment were the norm, not the exception, and “Free Your Mind” was an anthem to STFU and leave people be. –Samhita Mukhopadhyay

Listen: En Vogue, “Free Your Mind”


En Vogue: “My Lovin’ (You’re Never Gonna Get It)” (1992)

Lord help the man at the business end of an “Oooooooooooo BOP.” With its searing James Brown sample, stunning vocals, and biting parenthetical title, “My Lovin’” was En Vogue’s 1992 entry into the proud tradition of soul anthems by pissed-off women who were absolutely done being used and disrespected. But the four-member girl group from Oakland added the all-important squad element, and this dirtbag trying to sweet talk his lady back after treating her like crap never stood a chance. What makes you think you can just walk back into her life, indeed. –Evie Nagy

Listen: En Vogue, “My Lovin’ (You’re Never Gonna Get It)”

Kedar / Universal

Erykah Badu: “On & On” (1997)

Baduizm’s first single is quintessential literature in the Badu canon, and the neo-soul movement at large. Rarely was she the easiest narrator to interpret, but for as alluringly coded as “On & On” is, there’s a clear political undercurrent girding the track. “My money’s gone/I’m all alone” her sultry alto voice crooned over a slick four-note bassline, the first of many existential declarations—an opening address for a new generation of earth mothers, Afrofuturists, and doobie burners to follow like scripture. Despite—or because of—its elusiveness, the song has become one of the great chilled-out anthems for Black folks building new worlds in a country working hard on their demise. –Gio Santiago

Further Reading: Baduizm Sunday Review

Listen: Erykah Badu, “On & On”

Kedar / Universal

Erykah Badu: “Tyrone (Live)” (1997)

Mere months after lifting neo-soul to new heights with her 1997 debut Baduizm, Erykah Badu had the sheer confidence to release a full live concert album that included many of those same songs. It was a runaway hit, thanks in large part to the non-album radio single “Tyrone.” The titular proto-scrub was the buddy of Badu’s man, who never paid for anything and always brought his dirtbag pal along with buddies Jim, James, and Paul to everything they did together. Badu was always covering their asses, which is why she suggested her guy better call Tyrone to help get his shit out of her house, her voice oozing with raw, mesmerizing, sexy-as-hell contempt. The kicker—“But you can’t use my phone”—was a lyric that made exhausted girlfriends the world over scream with delight, and pledge devotion to the church of Baduizm for life. –Evie Nagy

Listen: Erykah Badu, “Tyrone (Live)”

So So Def

Ghost Town DJ’s: “My Boo (Hitman’s Club Mix)” (1996)

The original version of the Ghost Town DJ’s Miami bass classic “My Boo” was a dancefloor banger beloved by breakdancers and club kids but not exactly a breakout hit. The track didn’t take off until Chicago house legend DJ Mike “Hitman” Wilson put out his remix, with an extended three minutes of atmospheric groove over Virgo Williams’ haunting vocals. The DNA of “My Boo” runs across generations, from the Diplomats to a wobbly remix from witch house wunderkind Balam Acab. But the song is for dancing—it got a deserved second life when two kids from New Jersey started the viral Running Man challenge in 2016. 20 years after the original release, “My Boo” went from an IYKYK classic to a household tune. –Samhita Mukhopadhyay

Listen: Ghost Town DJ’s, “My Boo (Hitman’s Club Mix)”

550 / Epic

Ginuwine: “Pony” (1996)

“Pony” has got all the makings of a classic, sure: It’s one of Timbaland’s first major hits, its croaking vocoded “yea, yea, hell yea” beat is immediately recognizable at the club, and there are even ready-made dance cues. But there’s so much more. It can be a reach to project yourself into the panty-dropper protagonist of a sexy club anthem, but Ginuwine’s unbridled commitment to the bit (saddles! jockeys! ponytails!) has an earnestness to it, empowering even the least likely cowboy to jump on it. “Pony” is both the soundtrack to Channing Tatum’s Magic Mike dancing at his absolute peak, and a down and out Magic Mike cracking a smile and dancing alone in his wood workshop. After all, beyond the bit, “Pony” earns its enduring reign by being a genuinely fun and hot track to grind to—whether in the club or by yourself. –NM Mashurov

Listen: Ginuwine, “Pony”


Groove Theory: “Tell Me” (1995)

Groove Theory only had one album and one hit, but they made it count. “Tell Me” was a simple, sensual admission of affection by singer-songwriter Amel Larrieux that captured all of the genuine nerves and excitement accompanying bubbling romance, set over a heartsick and woozy groove. “If you thought I’d sleep on this/Boy, you're wrong ’cause all I dream about is our first kiss,” she sings, her voice both a sultry come-on and a raw confessional. All of this, combined with the unforgettable melody and producer Bryce Wilson’s bulletproof bassline, made “Tell Me” a near-perfect representative of the best that R&B could be. –Evie Nagy

Listen: Groove Theory, “Tell Me”


Guy: “Let’s Chill” (1991)

In 1991, it was not very out-there for musicians to be earnestly singing about love and commitment, or at the very least they weren’t prefacing those declarations with details about the ways they were also going to destroy your life (sorry, Drake!). But Guy, an impeccably dressed trio helmed by the rich-voiced Aaron Hall and new jack swing superproducer Teddy Riley, landed in the middle with “Let’s Chill:” a mid-tempo burner about how Hall’s devotion to his love will overcome his fear of commitment and create a beautiful life of coupledom, accompanied by acoustic guitar and freaky keyboard notes. Was it an R&B players’ anthem before R&B players became more overtly willing to gaslight? The video narrative says yes. But the candlelit tones in which they sweet-talked about eternity were too convincing, and hearts were forever won. –Julianne Escobedo Shepherd

Listen: Guy, “Let’s Chill”


H-Town: “Knockin’ da Boots” (1993)

“Knockin’ da boots actually means two boots coming together, making tasteful lust,” explains H-Town’s label boss Luther “Luke” Campbell, of 2 Live Crew, at the beginning of the “Knockin’ da Boots” video. Before long, his young signees launch into a tastefully lustful slow jam describing the night they would like to enjoy with a lucky lady. R&B men were leaning heavily into the realm of sexual fantasy and oiled-up desire in 1993, but the Houston trio’s hit stood out for its languid guitar flourishes and throaty entreaties; singers Keven “Dino” Conner, his twin brother Solomon “Shazam” Conner, and their friend Darryl “G.I.” Jackson harmonized with a polish that could make a horny grunt sound respectful. This was not in the same universe as Candyman’s player paean of similar etymological origins—H-Town offered a full-service establishment, the ladies only had to bring the towel. –Julianne Escobedo Shepherd

Listen: H-Town, “Knockin’ da Boots”

So So Def / Columbia

INOJ: “Love You Down” (1997)

The outstanding compilation series So So Def Bass All-Stars, helmed by Lil Jon and released by Jermaine Dupri, is an enduring time capsule of the earth-shaking collision of rap, R&B, and bass music that flourished in ’90s Atlanta. The compilations had a history of showcasing the label’s most resonant tracks, including “My Boo” by Ghost Town DJ’s and “Whatz Up, Whatz Up” by Playa Poncho. But “Love You Down” was its first original breakout hit, improbably landing a one-off compilation single at No. 25 on the pop charts. INOJ, the 21-year-old songwriter and part-time substitute teacher born Ayanna Porter, was initially asked to lay down some demo tracks for a cover of a 1986 quiet storm by Ready for the World for a more established artist to sing. But Lil Jon, who was So So Def’s head A&R at the time, heard it and knew it belonged to INOJ. Her voice was capable but understated, even a bit whispery—think Aaliyah, who she’d later befriend, or a ’90s predecessor to PinkPantheress. It supplanted the sticky sexual frisson of the original with an un-cloying sincerity that tempered the requisite propulsive sub-bass beneath her. Alongside “My Boo” and “Swing My Way,” “Love You Down” became one in a glorious triumvirate of iconic, women-helmed Atlanta rhythm & quad joints, destined to tether trunks to the dancefloor while transcending hearts into the sublime. –Julianne Escobedo Shepherd

Listen: INOJ, “Love You Down”


Janet Jackson: “If” (1993)

Janet Jackson is staring down an oblivious dude from across the room while thinking some very naughty thoughts. “If you like I’ll go down, da-down, down, down, da-down, down,” she mumbles in a hypnotic monotone, before opening up her voice to underline the innuendo, “Your smooth and shiny feels so good against my lips, sugar.” “If,” the fiercest track from her chart-obliterating janet. album, clears a path for her freakiest fantasies. The production, by Janet and her longtime collaborators Jimmy Jam and Terry Lewis, is a genre-defying riot—feral guitars that bring to mind prog rocker Robert Fripp smashed together with an artfully flipped Supremes sample and steel-hard hip-hop drums inspired by Public Enemy. Urged on by the turbocharged beat—and a dance-heavy video where Janet memorably pushes a guy’s head toward her crotch—this horny hypothetical of a song is fully realized. –Ryan Dombal

Listen: Janet Jackson, “If”


Janet Jackson: “That’s the Way Love Goes” (1993)

Ephemeral, transcendent, sensual, groovy—“That’s the Way Love Goes” is less a song than it is a vibe. From the first bouncy downbeat, your back relaxes, your head nods, and you let out a sigh: That is the way love goes. How can one feel so horny yet so chill at the same time? With Jackson’s whispering vocals over Jimmy Jam and Terry Lewis’ delicate, soulful beat, it is one of the greatest songs ever released about the overwhelming yet meditative pangs of lust, hypnotic, like desire itself. “That’s the Way Love Goes” was a mega-hit—the longest-running No. 1 single of any Jackson family artist—and the song, like the janet. album it appeared on, exposed us to a new Jackson: still soft-spoken but confident in her sexuality, her body, and her desire. –Samhita Mukhopadhyay

Listen: Janet Jackson, “That’s the Way Love Goes”


Janet Jackson: “Together Again” (1997)

On the surface, “Together Again” borders on Hallmark-card triteness: It features a childlike, major-key melody, a peppy disco-house beat, and a hook that goes, “Everywhere I go, every smile I see/I know you are there smilin’ back at me.” But Jackson wrote the lyric about personal friends she’d lost to AIDS, and the song’s co-mingling of plucky cheerfulness and crestfallen grief makes it both winsome and wistful, echoing the spirit of the Supremes’ classic “Someday We’ll Be Together.” In 1997, the world was in the second decade of the AIDS crisis, yet few mainstream pop stars had creatively responded to the epidemic, despite the deaths of musicians like Freddie Mercury and Eazy E, and the disproportionate effect of HIV and AIDS on LGBTQ+ communities of color. By paying tribute to the departed, this No. 1 hit became an intervention, a cause—an upbeat rallying cry when we needed it the most. –Jason King

Listen: Janet Jackson, “Together Again”

So So Def

Jagged Edge: “He Can’t Love U” (1999)

True to their name, Jagged Edge made a career out of being sweethearts with a penchant for fuckery. The quartet emerged under Jermaine Dupri’s So So Def banner as the more rugged, baggy-jeans-and-Timbs heirs to groups like Boyz II Men, singing about the pros and cons of someone loving them at their worst. “He Can’t Love U,” from their sophomore album J.E. Heartbreak, opens with a melting series of “oohs,” an admission of deceit, and even some accountability. The group then gets tender about losing a good love, presenting a resumé of reasons why they’re better partners than the next guy. It’s one of the oldest and most effective tricks in the R&B book, paired with angelic harmonies that plead for redemption. As it happens, some of the sweetest love songs in the world come from men who’ve made mistakes. –Clover Hope

Listen: Jagged Edge, “He Can’t Love U”

Uptownn / MCA

Jodeci: “Feenin’” (1994)

With songs like “Feenin’,” one of the most literal interpretations of addictive love, Jodeci single-handedly turned begging into a pastime. Under the tutelage of Puff Daddy, the group’s four members—K-Ci, JoJo, DeVante, and Mr. Dalvin—became the bad boys of R&B, providing the soundtrack to young adult libidos. On this single from their second album Diary of a Mad Band, they croon about being so hooked on someone that they’re willing to sacrifice their money, car, and home for a few freaky moments. R&B holds a monopoly on the category of songs that compare love to narcotics, where desire is all pheromones and dopamine. Amplifying that point, “Feenin’” makes marvelous use of the vocoder, conveying straight-up lust with a sacrilegious tinge of gospel. No group was better at boiling horniness down to its most primal parts. –Clover Hope

Listen: Jodeci, “Feenin’”


K.P. & Envyi: “Swing My Way” (1998)

“Swing My Way” posited an unfortunately uncommon scenario for ’90s R&B: A woman is so determined to talk to the fine young man she spots in a club that she beelines to make the first move. The era was still inching out of basic double standards for women, so the suave initiative exhibited by K.P. when she rapped, “I know that you don’t know me/But this might be my only/Shot at a tenderoni,” or in Envyi’s sensuously unbothered chorus—“Shorty swing my way… you sure look good to me”—was instantly anthemic for a certain cohort of young club-going women. Some might consider this gossamer bass track a one-hit wonder, but there were enough variations that it comprised practically five different perfect songs (let’s hear it for the era of the extended single). The video, which stars a baby-faced future rap star Polow da Don as the shorty in question, was K.P.-led and more hip-hop-forward with an indelible hook. But on the “Carl Mo Radio Remix With Rap,” with a K.P. verse written by Ludacris, we got more backstory: The shorty in question is—gasp—a dog, but she doesn’t care. If you haven’t heard, this man is extremely fly, and tonight, that’s all she needs. –Julianne Escobedo Shepherd

Listen: K.P. & Envyi, “Swing My Way”


Kelis: “Caught Out There” (1999)

Kelis has said that “Caught Out There,” her debut single, recorded when she was just 20 years old, “set the tone for my entire life.” It was an early and formative Neptunes production, with bouncy keyboards and a pew-pew sound effect that can only be compared to laser guns, but their collaboration eventually soured. It was ahead of its time, which meant the timing was off, which makes it a “cult favorite”—a euphemism for “not as popular as it should have been” and a way of signaling taste and discernment that would, rather unfairly, dog Kelis for much of her career. But it was also an anthem for women’s aggrievement, the song that made her, with its ferocious, shouting hook, “the first girl to scream on a track,” as she would later remind us. For all she’s been through over the years, it makes sense that Kelis came out kicking. –Emma Carmichael

Listen: Kelis, “Caught Out There”

Ruffhouse / Columbia

Lauryn Hill: “Ex-Factor” (1998)

Like any great breakup song, “Ex-Factor” has its own mythology: It was reportedly written about Lauryn Hill’s affair with Wyclef Jean, her former Fugees bandmate. But does that even matter? It’s a plea that will serve as a balm for anyone and everyone as long as hearts are getting broken. Featuring one of Hill’s all-time great vocal performances, the song’s genesis alone spans generations and genres: The unsettlingly plaintive opening line is adapted from a Wu-Tang Clan sample of a Gladys Knight & the Pips’ cover of Barbra Streisand’s “The Way We Were”; Hill’s track, in turn, has been sampled countless times since. And with its encouraging ad-libs, it almost sounds like a private duet with and to herself, a reminder in the margins that she—just 23 when she wrote it, yet possessing razor-sharp emotional clarity—deserves better. –Emma Carmichael

Listen: Lauryn Hill, “Ex-Factor”

WEA / Atlantic

Mark Morrison: “Return of the Mack” (1996)

In hindsight, there’s a slight irony to the massive success of “Return of the Mack,” given that Mark Morrison was never quite able to capitalize on his deliciously petty signature song: It’s a return in search of a departure, a comeback without a debut. In the years that followed his smash hit, a slick and triumphant British Invasion of the American R&B charts with a heavy ragga-tinged beat, Morrison’s career would implode due to constant legal troubles—most infamously the time he hired a lookalike to do his court-mandated community service while he went on tour. The resentment and bitterness exemplified by his lone hit might have been Morrison’s undoing when it came to career longevity, but “Return of the Mack” spins negativity into cathartic gold, a walking-on-air anthem designed to be played on repeat during those times when you need to manifest sweet comeuppance into reality. –Nadine Smith

Listen: Mark Morrison, “Return of the Mack”

Uptown / MCA

Mary J. Blige: “Real Love” (1992)

Between its main radio edit and its various 12" remixes, Mary J. Blige’s “Real Love” came with several different introductions: If the tune’s “Top Billin’” drumbeats didn’t grab you, maybe starting with the guitar riff from “Clean Up Woman” or Mary’s jazzy a cappella ad-libs would. Her raw gift for impromptu gospel and jazz singing paralleled the improvisational impulses of rising MCs and hip-hop DJs; so when Biggie Smalls added a few bars to the remix, you heard his rhymes juxtaposed against isolated melodic phrases that revealed structural similarities in Blige’s delivery. In an era when danceable rap records were increasingly crossing from Black radio to “pop” stations, “Real Love” wed roller-disco tempos to B-girl vulnerability. The combination of kinetic rhythms and passionate, confessional vocalizing became the signature sound for the emergent Queen of Hip-Hop Soul. –Carol Cooper

Listen: Mary J. Blige, “Real Love”


Maxwell: “Ascension (Don’t Ever Wonder)” (1996)

Is Maxwell talking about love on “Ascension (Don’t Ever Wonder),” the second single from Maxwell’s Urban Hang Suite? A woman? God? Drugs? Maybe all of the above, which is why the chorus penetrates your soul: You know the feeling when something takes you to a place you’ve never been before. The album sequencing suggested it was about the throbbing crescendo of intimate and sexual love, which didn’t stop the song from being beloved by church choirs—it is, after all, a Biblical reference. The track evokes an ethereal lightness, an angelic warmth that hugs you and elevates you higher, above yourself, to a new tier of consciousness. –Samhita Mukhopadhyay

Listen: Maxwell, “Ascension (Don’t Ever Wonder)”


Mint Condition: “Breakin’ My Heart (Pretty Brown Eyes)” (1991)

“Pretty Brown Eyes,” as it’s colloquially known, remains integral to the R&B conversation—see, most recently, the strip club-set TV show P-Valley’s second-season finale, which prominently featured the song, plus a surprise TikTok revival. That’s not just because it was a massive hit, but because it’s timeless without being formulaic, a track that embodies everything brilliant about perfectly placed harmonies and the unknowable effervescence of yearning. Mint Condition was a six-person band from Minneapolis that played locally before being discovered by producers and consummate ears Jimmy Jam and Terry Lewis. “Pretty Brown Eyes” captured their classic First Avenue funk while sounding firmly modern, even amid a youthful R&B landscape that was increasingly dominated by new jack swing. Lead singer Stokley Williams’ voice was crystal clear and had an emotional fortitude that felt zeroed in, like he was singing directly to each individual listener. In less capable hands, you might have wondered why this man can’t accept rejection; via Williams’ heartfelt treatise, though, it’s clear his love interest is playing coy, and if she doesn’t want the honey, there’s a whole globe of us swooning in the wings. –Julianne Escobedo Shepherd

Listen: Mint Condition, “Breakin’ My Heart (Pretty Brown Eyes)”

Rowdy / Arista

Monica: “Don’t Take It Personal (Just One of Dem Days)” (1995)

Monica was just 14 when she dropped her debut single, and yet she intuited the girls of the world needed a song to validate our shittiest feelings at our shittiest moments. (“Just One of Dem Days” is was not, however, about PMS, as was widely believed at the time.) By making a tender anthem about the need to have some space to herself, she encapsulated the debilitating feelings of depression, anxiety, confusion, and maybe a little bit of agoraphobia with a sweetly earnest explanation. She also made it OK for young girls at the time to recognize they even could ask for space, and that feeling angry sometimes was natural—maybe not revolutionary in 2022, but deeply necessary in the weird-ass ’90s. And she did so with one of the strongest voices in R&B over a mid-tempo hip-hop beat. Shout out to the track’s producers, which included Dallas Austin, for recognizing the power in placing a sample of Public Enemy’s “Bring the Noise” on a song about a young woman’s agency. –Julianne Escobedo Shepherd

Listen: Monica, “Don’t Take It Personal (Just One of Dem Days)”

Def Jam

Montell Jordan: “This Is How We Do It” (1995)

Montell Jordan was 26 when he dropped “This Is How We Do It”—young in human terms, relatively old for a debut in the ’90s music industry. Despite the song’s buoyant new jack beat, courtesy of producer Oji Pierce and a Slick Rick sample, he sounded like a wizened sage dispensing crucial party advice. He was confident, electrified, and told us exactly how a legendary night should function. Find a designated driver? Yup. Don your cleanest Karl Kani? Yup. Celebrate your come-up in a big black truck? Yup-yup. Impress your barber? The man is a block-party god. Jordan was specifically celebrating his life in South Central Los Angeles, which was cast asea by various levels of government and condescending white media in the mid-’90s. But his pluck and bombast resonated globally, and still does: It’s the song that you pray comes on at the club right when you roll up. –Julianne Escobedo Shepherd

Listen: Montell Jordan, “This Is How We Do It”


Next: “Too Close” (1997)

This paean to getting aroused at the club flips Kurtis Blow’s 1979 classic “Christmas Rappin’” into a sexy, mid-tempo groove perfect for two-stepping and consensual grinding. There’s no need to untangle the message here with lyrics like, “I feel a little poke coming through,” or, “It’s almost like we’re sexin’.” The song shot to No. 1 and sat there for five weeks, revealing just how many people really, really love to dance. –Clover Hope

Listen: Next, “Too Close”


The Roots: “You Got Me” [ft. Erykah Badu and Eve] (1999)

“You Got Me” is a short story and a love song, a duet for three voices and a collective arrival, a ballad that enters with classical guitar arpeggios and exits with a drum‘n’bass break. It’s also the lead single from Things Fall Apart, the Roots’ fourth studio album, recorded with the hopes of helping them finally break big. The devil’s bargain? Switching out Jill Scott, who co-wrote the song, for Erykah Badu, the neo-soul queen of the moment. (The band made up with Scott later by taking her on tour.) Meanwhile, the song—a lovers’ back-and-forth, with Black Thought as the male lead and the female character split between an Eve verse and Badu’s gentle, reassuring vocals—stuck, and helped propel the Roots to the mainstream. Despite the melancholic tone, the song is comforting, committing to the kind of care that keeps a relationship going strong despite the turbulence—as true for the track’s collaborators as for its fictional protagonists. –NM Mashurov

Listen: The Roots, “You Got Me” [ft. Erykah Badu and Eve]


Sade: “No Ordinary Love” (1992)

If there’s one song that harnesses Sade’s capacity for aquatic melancholy, it’s “No Ordinary Love.” This isn’t only because of the music video’s marine setting, which depicts lead singer Sade Adu as a brooding mermaid who aspires to be a human bride. There are the chugging guitars in the chorus, which crest like the peak of ocean waves; the fluid fog of synths that floats over sparse percussion; and of course, the unrelenting devotion central to the lyrics, which become liquid velvet between Adu’s lips. The oceanic aura that surrounds “No Ordinary Love” might be mellow, but it’s also one of the UK band’s most piercing and desolate moments. After all, that’s what love feels like when it’s elusive, especially after you’ve emptied yourself in service of another: as isolating and bottomless as the sea itself. –Isabelia Herrera

Listen: Sade, “No Ordinary Love”


Shanice: “I Love Your Smile” (1991)

That doo-doo-doo-doo refrain: a starburst melody that simultaneously feels like it must have always existed and was surely beamed to Shanice from the heavens in a moment of celestial magic. “I Love Your Smile” is all about young romance and the joy that uncontrollably bursts from your chest cavity. Funky drums and a prominent bassline adds a streetwise undercurrent to the singer’s effervescence. Though the radio edit foolishly omits Shanice’s rap verse, her rudimentary rhymes attest to feelings of doubt, with the sound of thunder bringing a sudden seriousness to her voice. But then she releases the tension with a laugh, making way for a sax solo by none other than Branford Marsalis, the sun bursting through the clouds once more. –Dean Van Nguyen

Listen: Shanice, “I Love Your Smile”

Keia / Elektra

Silk: “Freak Me” (1993)

Chart-climbing R&B boys were extra horny in the mid-’90s. Case-in-point: Silk, who were gonna give you an exact play-by-play of how they’d like to do you. (It is no coincidence that Keith “Gonna Make You Sweat” Sweat discovered the Atlanta quartet and helped them write “Freak Me.”) There was licking, there was dripping, there was whipped cream, there was a reasonably submitted request to “take a sip.” The group’s impeccably churchy vocal runs were part of this song’s salacious magic—“I wanna lick you up and down till you say stop” never sounded so godly, nor so respectful of informed consent. Was the country scandalized? Sure. So much so that “Freak Me” spent a few months atop the pop charts and helped open the floodgates for generations of lovable hornballs. –Julianne Escobedo Shepherd

Listen: Silk, “Freak Me”


Soul for Real: “Candy Rain” (1994)

On their debut single, the brothers of Soul for Real found the smoothest way to describe what it’s like to meet your perfect match. You can practically envision the boys sitting at a desk to write a heartfelt letter to their honey: “My love, do you ever dream of candy-coated raindrops?” An accomplished rapper and producer, the late Heavy D helped sign Soul for Real to Uptown Records and infused the new jack swing DNA he inherited from the subgenre’s architect, Teddy Riley, into this breakout hit. The song is a sweet rush of drums and endless charm that inspires you to do all kinds of spin moves on the dancefloor. It’s proof that our most formative feelings stick to us for a reason, even as we grow simultaneously wiser and stupider. –Clover Hope

Listen: Soul for Real, “Candy Rain”


SWV: “Right Here (Human Nature Remix)” (1992)

In the comments section for a four-minute YouTube clip from 1993’s Free Willy, hundreds have communed to honor a cinematic moment from childhood that gave them “chills.” As Willy’s fins cut through the water, the sound of Michael Jackson’s reinterpolated “Human Nature” shimmers like the sun-jeweled waves, and the sound of SWV’s voices gently rain down like drops of holy water. Chills. Sitting somewhere snug between the ecstatic and absolute serene, SWV’s “Right Here (Human Nature Remix)” belongs as much in the church as it does the Free Willy soundtrack. With its gospel-infused harmonies, Teddy Riley’s remix combines the classic romanticism and cool insouciance of the original with updated, widescreen hip-hop production (including a cameo from his protégé, Pharrell). –Emma Madden

Listen: SWV, “Right Here (Human Nature Remix)”


SWV: “Weak” (1992)

Producer and songwriter Brian Alexander Morgan originally wrote “Weak” for the Gap Band’s Charlie Wilson, as an ode to another R&B star, Chanté Moore. Morgan’s song about an unrequited crush ended up in the hands of SWV, a trio of friends who were masters of creamy, gospel-inspired soprano harmonies. The effortless serenade, which cedes the floor to the trio’s floating vocals, topped the pop charts for two weeks. It’s a cruel irony that the physical sensations of love tend to show up in the body’s most vulnerable places, like the knees and the heart. But there’s something to the idea of describing this feeling as an amazing sort of vulnerability, one that’s not worth fighting against. –Clover Hope

Listen: SWV, “Weak”


Tevin Campbell: “Can We Talk” (1993)

At this point, given its lyrics about eyeing a stranger at night, the single from Tevin Campbell’s sophomore album I’m Ready has been reconsidered for what could seem like stalker behavior. The truth is, we’ve all planned a conversation in our heads after experiencing love at first sight. Campbell got in on the joke in 2020, tweeting that “‘Can We Talk’ is a song about stalking but it works every time.” More accurately, it’s an anthem for shy people who struggle with sweet talk. Written and produced by Babyface, it’s the MTA Missed Connections of its time, the innocent musings of a teenybopper left in a daze over a special someone, all cautious glances and covert obsessions. –Clover Hope

Listen: Tevin Campbell, “Can We Talk”

LaFace / Arista

TLC: “Creep” (1994)

Anchoring their classic 1994 album CrazySexyCool, “Creep” is TLC’s mischievous justification for revenge cheating on a partner who’s abandoned any sense of trust. Smooth, decisive, and almost numb in her delivery, T-Boz sells the feeling of emotional detachment with her signature deep rasp, relaying a message that sometimes the most cathartic response to a messy relationship is to get even messier. Today’s R&B is so rich with women doing dirt that it’s almost quaint to remember an era when a song about a woman cheating as emotional retribution was an aberration. It’s a feat that she waited until the 22nd of loneliness to do so. –Clover Hope

Listen: TLC, “Creep”

LaFace / Arista

TLC: “No Scrubs” (1999)

“No Scrubs” is a cold-hearted diss, but it’s also a song about putting your foot down and finally valuing your self-worth. It would be mean if it wasn’t so funny, especially when they nail the specifics on the bridge: Guys that don’t have a car should keep it stepping, and if your mom is your roommate don’t even try to waste their time. Most of all, it sounds beautiful: Chili’s strong and sweet lead vocals, the angelic background harmonies, the futuristic flourishes of the instrumental, Left Eye’s robotic raps preserved in arguably the definitive Hype Williams music video. It remains the holy grail of deadbeat boyfriend ethers, a sentiment frequently captured but not with the balance of theatrics and truth that TLC had down pat. –Alphonse Pierre

Listen: TLC, “No Scrubs”

LaFace / Arista

Toni Braxton: “You’re Makin’ Me High” (1996)

The lead single from Toni Braxton’s sophomore set Secrets is perhaps best remembered for its playful video: When Braxton isn’t gyrating in a skin-tight white catsuit, she and sitcom gal pals Vivica A. Fox and Erika Alexander size up handsome dudes as they ride up an elevator shaft. The R&B tune—a collaborative effort between Braxton, Babyface, and Bryce Wilson of Groove Theory—skillfully captures the feeling of unbridled lust. Its bass-heavy beat oozes along at a blunted tempo, evoking both ’70s Barry White and ’80s Steve Arrington, as Braxton sings a lyric racier than anything we’d heard from her before: “I can imagine you touching my private parts.” The real centerpiece is her sultry, thick-as-molasses alto—no vocalist of the ’90s better embodied the allure of body heat. –Jason King

Listen: Toni Braxton, “You’re Makin’ Me High”


Tony! Toni! Toné!: “Feels Good” (1990)

“Play this record as frequently as possible. Then, as it becomes easier for you, play the record once a day or as needed.” The old-timey voiceover that introduced the Oakland trio’s first big song set a high bar that this tune would be the cure for what ailed listeners, but that first drum hits like a full syringe of serotonin. With all the sweet harmonies and big beats that defined new jack swing, “Feels Good” stands out as a titan of the genre, a full-bodied five-minute mission to live up to its name, and a catalyst for the prolific career of artist-producer Raphael Saadiq. One of the thousands of songs to sample Lyn Collins’ 1972 James Brown-produced “Think (About It),” “Feels Good” drew heavily from older funk, soul, gospel, and jazz, while also embracing the hard-hitting sound of the era. It was part love song to a girl, part love song to music in general, and all party. –Evie Nagy

Listen: Tony! Toni! Toné!, “Feels Good”

Tommy Boy / Warner Bros.

Total: “Can’t You See” [ft. The Notorious B.I.G.] (1995)

Compared to the powerhouse singers of their era like SWV and En Vogue, Bad Boy’s resident trio Total was more focused on mood-setting than vocal flexing. With their cropped hairdos and perpetual midnight-dark shades, they were too cool for school, with deeper tones attuned to the rhythm of a then-growing alliance between hip-hop and R&B. At this point, Puffy was intent on blending the street and the chic on every record his label produced, and Total was a proof of concept. The Notorious B.I.G. is a looming presence on their debut single “Can’t You See,” with an opening verse that doubles as a statement of his own formidability and for that of his labelmates, who sound as smooth as camel hair, singing about fairytale love over a funky loop of James Brown’s 1973 hit “The Payback.” You can’t help but make like Puffy and do a little shoulder bounce to it. –Clover Hope

Listen: Total, “Can’t You See” [ft. The Notorious B.I.G.]

LaFace / Arista

Usher: “You Make Me Wanna…” (1997)

My Way was a path-changing album in Usher’s discography, and on a record where every song had the potential to break out, “You Make Me Wanna…” had to be particularly spectacular to slightly edge out the others. A sublime mix of hip-hop cool and R&B seduction in the vein of Usher’s idol, Bobby Brown, the song is sexy without being lascivious, playful without any childish inclinations, and just a little unbelievable. It’s common to mourn the “death” of smooth, danceable and carefully produced R&B—an apparent bygone of a lost era—yet Usher’s artistry has revealed itself to be committed to his roots, with a deep awareness of the foundational pillars lent to the genre by gospel and soul. As the years have passed, he’s shifted and experimented, all the while pledging allegiance to the melodies that raised and introduced him. –Tarisai Ngangura

Listen: Usher, “You Make Me Wanna…”


Zhané: “Hey Mr. DJ” (1993)

It’s a simple and resonant concept—where’s the DJ, where’s the party?—but within it, the Philadelphia singers Renée Neufville and Jean Norris captured a feeling that threaded the disco era to the current moment: The floor, filled with dancers desperate for release, needed to be fed. Its soulful Rhodes piano line, borrowed from Michael Wycoff’s 1982 single “Looking Up to You,” helped capture the universality of feel-good club elation, with lilting vocals that emphasize the freedom a dancefloor engenders, particularly at the start of the weekend, when everybody needs to move their bodies and shake off their worries. It’s a worthy celebration of DJs everywhere, which is probably why they stay playing this at the most convivial parties. –Julianne Escobedo Shepherd

Listen: Zhané, “Hey Mr. DJ”