The 50 Best R&B Songs of the 2000s, Ranked (2000-09)

Producer: The Neptunes
Album: The Neptunes Present... Clones
Label: Star Trak/Arista

Originally written for Prince, “Frontin’” went from being the Purple One’s trash to Skateboard P’s treasure, kickstarting a solo career that would have pop culture in a chokehold for years. The space-age bounce and warped ambience provide the perfect backdrop for Pharrell to spit game, while Jay-Z makes light work of a quick eight bars that everyone and their cousin in 2003 had down pat. —Will “ill Will” Lavin

Producers: Music Royale, Rudy Sandapa & Static Major

Album: Late Night Special

Label: Atlantic/Bluestar

Some R&B acts rush to the bedroom in their sex-driven material, but Florida boy band Pretty Ricky were the masters of foreplay. The group incorporated the lust that fueled their 2005 debut, Bluestars, and sonically turned it into an effective “You up?” anthem.

Pleasure P takes command on the song’s Salt-N-Pepa-referencing chorus; Baby Blue gives an indirect nod to Ying Yang Twins’ “Wait (The Whisper Song)” by murmuring teases into the receiver; Slick'em jolts out with stamina that would make the Energizer Bunny blush; and the eternally cool Spectacular fantasizes about putting the booty call to action. Nearly two decades later, there’s still plenty of ladies on their line. —Jaelani Turner-Williams

Producers: Timbaland, Justin Timberlake, and Nate "Danja" Hills

Album: FutureSex/LoveSounds

Label: Jive

Love notes and symphonies have never sounded as good as they do on this frequency-melting masterpiece.

A romance plea packed full of twists and turns, the song finds Timbaland’s wall of sound putting Justin Timberlake’s R&B pop cocktail in an echo chamber, resulting in a sonic sci-fi epic that Stanley Kubrick would be proud of.

Arriving on the heels of “SexyBack”—the launchpad for JT and Timbo’s space odyssey—it had some big shoes to fill. But thanks to the futuristic chord stabs, glitched-out beatboxing, cartoon sound bites, and Timberlake’s gear-shifting vocals, as well as a standout verse from T.I., it took over the airwaves. —Will “ill Will” Lavin

Producers: Michael Jackson and Andre Harris

Album: Invincible

Label: Epic Records

The King of Pop went neo-soul for the second single off his final studio album, Invincible. “Butterflies,” co-written by songwriter/producer Andre Harris and Floetry’s Marsha Ambrosius, is a mid-tempo ballad with a pretty chord progression, but the showstopper here is MJ’s falsetto. The song, which has a touch of old-school Philly soul, peaked at No. 14 on the Billboard Hot 100 and No. 2 on Billboard’s Hot R&B/Hip-Hop Singles chart and was Jackson’s last hit single in America while alive. —Thomas Golianopoulos

Producer: Ryan Leslie

Album: Cassie

Label: Bad Boy Entertainment/NextSelection Records/Atlantic Records

From nightclubs to 106 & Park to the now-obsolete social media platform Myspace, Cassie’s breakthrough single was inescapable. Still a teenager, Cassie exuded millennial coolness and tongue-in-cheek horniness over minimal synths courtesy of producer Ryan Leslie. She wasn’t a vocal powerhouse, but her first and only mainstream hit closely emulated the laid-back swagger of her idols, Aaliyah and Janet Jackson—with the video even referencing the latter’s “Pleasure Principle.” —Jaelani Turner-Williams

Producers: Gregory Curtis and Ron Fair

Album: The Way It Is

Label: A&M/Interscope

Few singers documented the woes of toxic relationships like Keyshia Cole. The singles from her debut find her wrongly accused (“I Should Have Cheated”), on the verge of a breakup (“[I Just Want It] To Be Over”), and finally done (“I Changed My Mind”). “Love” was the last single from the album but thematically it sits right before “I Changed My Mind”: the relationship has ended, but the wound is still open and the pain is unbearable. The production is lush and cinematic, but the song endured because of Keyshia’s vocals, specifically that climactic note she reaches for and maybe doesn’t quite hit. Or does she? —Dimas Sanfiorenzo

Producers: Pro-Jay and Robin Thicke

Album: The Evolution of Robin Thicke

Label: Star Trak Entertainment/Interscope Records

To this day, only the guests at Michael Jordan and Yvette Prieto’s 2013 wedding reception, in Jupiter, FL, know for sure which tune Robin Thicke sang for the happy couple. Perhaps it was an album cut (“Would That Make U Love Me” is a great one, though situationally inappropriate), but it’s more likely that Thicke went with his breakthrough hit.

The bossa nova-tinged ballad “Lost Without U,” with its memorable acoustic guitar from co-writer Sean Hurley (of Vertical Horizon), spent 23 weeks on the Hot 100, peaking at No. 14 in March 2007. It also hit No. 1 on the R&B/Hip-Hop Songs chart, putting Thicke in the rarefied company of white-chocolate genius George Michael, the last solo white male artist to top that chart (then called Hot Black Singles), with 1988’s “One More Try.” It’s also conceivable that Thicke sang “Blurred Lines,” then a brand-new single on its way to becoming the second-biggest song of 2013, for a “fun” and “flirty” moment.

But only one of these songs is truly timeless. —Ross Scarano

Producer: Mark Batson

Album: Comin’ from Where I’m From

Label: So So Def/Arista

Imagine listening to the radio in the fall of 2004, and you’re hearing bright, slick crossover singles from Usher, Ciara, maybe Mario. And then, suddenly, a mournful Hammond organ that sounds like loss, super-dry percussion, and a voice straight out of Stax, with the expressive grain and emotional clarity of Southern gospel, and this voice is pleading. “Come on home to me, Charlene.”

Beginning in the early 1990s, Anthony Hamilton worked for years to break into the industry, impressing the late Andre Harrell and writing for Donell Jones. He sang backup on D’Angelo’s legendary Voodoo tour before releasing Comin’ from Where I’m From, with his signature song “Charlene.” To fully appreciate his talents, listen to the live version, stretched to seven minutes and unfurling in a way radio wouldn’t have permitted. —Ross Scarano

Producer: Teddy Riley and Roy “Royalty” Hamilton

Album: My Name Is Joe

Label: Jive Records

Flipping the script on infidelity, Joe goes to bat for the fellas. The off-kilter guitar loop and skittish castanets transform a luscious R&B groove into an eerie anthem that puts listeners on edge as Mr. Thomas interrogates his lady. The lyrics toe the line of paranoid delusion, and the video, which features some toxic behavior that wouldn’t fly in today’s climate, reveals Joe fucked up: it was his girl’s evil twin creeping all along.

The Mystikal remix, on which the former No Limit soldier barks at the accused, adds an extra layer of aggression—which, considering he’s now serving 20 years for rape, hasn’t aged well. —Will “ill Will” Lavin

Producers: Midi Mafia & Mzmeriq

Album: Fantasia

Label: 19/S/J

Even after winning American Idol and releasing a platinum debut, there was still a plenty of uncertainty around Fantasia. The first single from her sophomore album, “Hood Boy,” was a brick, despite having a feature from Big Boi. It turns out that song had too much ’tude, and what was needed was something sweeter. The follow-up single not only saved the album—helping it ship gold—but has the warmth of a high school crush. It’s as tender as it gets, which somehow made it perfect for a gang of subversive remixes we got from rappers over the years (from Remy Ma to Styles P to Foolio’s twisted version). —Dimas Sanfiorenzo

Producer: Tim & Bob

Album: Bobby Valentino

Label: Disturbing tha Peace/Def Jam

Formerly of the short-lived R&B teen quartet Mista, Bobby V. (formerly Bobby Valentino) extracted the southern soul from his boy band heyday into the romantic pining of his solo debut single “Slow Down.” The track soars in like a rhythmic symphony before an Eastern-influenced drum pattern kicks in, but by then, Bobby’s caught between wanting to get to know an eye-catching woman and admiring her backside. All men could relate. —Jaelani Turner-Williams

Producers: Maxwell and Hod David

Album: BLACKsummers’night

Label: Columbia Records

“Pretty Wings” is a tearjerking juxtaposition that pairs a painful goodbye with a soundscape so delicate it’s become a slow-jam playlist staple. Whether it’s the twinkling wind chimes, the build of the slow-moving acoustic guitar, or the subtle pulse of the bass, it plucks at the heartstrings in a way not many songs can. It’s hard not to get into your feelings. The songwriting is a triumph, too, and Maxwell’s angelic falsetto and sensual phrasing turn what would be a complicated vocal workout for most into an effortless display. —Will “ill Will” Lavin

Producer: Tim & Bob

Album: Nutty Professor II: The Klumps (soundtrack)

Label: Def Jam

Case had already given us R&B classics like “Touch Me Tease Me” and “Happily Ever After” before “Missing You” arrived on the Nutty Professor II soundtrack in 2000. The song gave his rough-edged voice a melody worth fully surrendering to. He sounds miserable. By the end, when he cries, “I can’t sang no more!”—the ad-lib is both hilarious and unforgettable—the kind of spontaneous moment that can make or break a song. This one made it. And here, the line was more literal than anyone realized: Case’s voice was actually giving out. —Kia Turner

Producer: The Neptunes
Album: Tasty
Label: Star Trak/Arista

The Neptunes were on some different shit when they cooked up the eccentric electro-R&B beat for “Milkshake,” and Kelis met it with one of the catchiest hooks of the century. More than two decades later, it’s still fueling viral moments. Just look at KATSEYE’s 2025 Gap ad. —Antonio Johri

Producers: Jasper Cameron and Big Reese

Album: Street Love

Label: The Inc./Universal Motown

A little Spandau Ballet interpolation and a lot of hood edge were the perfect recipe for Lloyd’s comeback single. As the lead-up to his sophomore album, Street Love, the crooner had all the right elements to make “You” a classic mid-aughts R&B staple: a prime Lil Wayne spitting game on two verses, a sunny beat and four minutes of straight yearning that would make any woman give in. ——Jaelani Turner-Williams

Producer: Dre & Vidal
Album: Who Is Jill Scott? Words and Sounds Vol. 1
Label: Hidden Beach Recordings/Epic Records

“A Long Walk” is about the ideal first, second, or third date. Jill Scott takes a simple concept—savoring the joys of living in an urban, walkable metropolis—and turns it into something romantic and beautiful. And most importantly, it oozes sex and connection. It’s lyrical like a rap song without featuring gratuitous verses from rappers. Scott is a power vocalist, but for most of the song she embraces a more conversational cadence. ’Cause we could all use a little “Temptation, education, relaxation.” —Dimas Sanfiorenzo

Producers: Missy Elliott and Cainon Lamb

Album: Fearless

Label: J

Philadelphia is known for its dramatic soul, and Jazmine Sullivan’s debut, Fearless, has plenty of it. But the album also showed how wide her influences ran, from ’90s New York hip-hop (“My Foolish Heart” uses the same source code as GZA’s “Liquid Swords”) to French electronic music (“Dream Big” samples Daft Punk’s “Veridis Quo”). Lead single “Need U Bad” is built on an infectious reggae groove, which is juxtaposed by a tender Sullivan vocal performance, while Missy Elliott adds a typically showy, slightly shticky cameo at a time when she rarely popped up on other people’s records. —Dimas Sanfiorenzo

Producer: Dr. Dre

Album: No More Drama

Label: MCA

After a decade of suffering and heartbreak, Mary J. Blige deserved some relief, so she went to the club. The lead single from her fifth album paired her with Dr. Dre and gave her the first (and, to date, only) Hot 100 No. 1 of her career.

Originally cooked up for Rakim’s shelved Aftermath album, “Family Affair” might be the most Dr. Dre-sounding Dr. Dre beat of all time, built on dramatic strings, staccato keys and stomping drums. Mary meets it at her most carefree, from the video’s swinging dance moves to “hateration,” a neologism still in circulation a quarter century later. —Dimas Sanfiorenzo

Producer: Buckwild, Mario Winans and Diddy

Album: Faithfully

Label: Bad Boy Entertainment/Arista Records

“I Love You” took some luck to happen. Buckwild, the principal producer, first made the beat for O.C., who passed on it. Years later, Jennifer Lopez, who has a writing credit on the song, was set to record it before bailing at the last minute. It was for the best. Over a flip of Isaac Hayes’ “Make a Little Love to Me,” Faith brings a vulnerability that J.Lo’s diva persona couldn’t have pulled off. She’s playing a role usually reserved for R&B’s leading men: the yearner whose love is just out of arm’s reach. —Dimas Sanfiorenzo

Producers: Stargate and Ne-Yo

Album: Year of the Gentleman

Label: Compound/Def Jam

The packaging around Ne-Yo’s third album, Year of the Gentleman, was all throwback, paying homage to Frank Sinatra and the Rat Pack with lots of suits and fedoras. And yet the music was the most modern of the singer’s career: synth-heavy club boppers that bordered more on pop than the traditional R&B of songs like “So Sick.” “Miss Independent” is kind of an R&B cliché (an uplifting salute to all the burgeoning girl bosses of the era), but it’s so bright, radiant, and charmingly cheesy that it’s no surprise it lives on as one of his biggest hits. —Dimas Sanfiorenzo

Producers: Mike City and Carl Thomas

Album: Emotional

Label: Bad Boy/Arista

With what might be one of the coldest lines in all of R&B—“And I wish I never met her at all”—Carl Thomas turns a sticky situationship into a canon-level tale of heartbreak. The icy bite of the opening piano chords kicks off a tug-of-war that, to this day, has never hurt so good. Never oversinging, the Bad Boy singer wraps his regret around a dramatic synth that creeps in under the song’s hushed drums, and that bittersweet mix is as potent now as it was back in 2000. —Will “ill Will” Lavin

Producers: Polow da Don and Blac Elvis

Album: Ciara: The Evolution

Label: LaFace/Zomba

Ciara had a noisy introduction, taking the rugged sounds of crunk and turning them into good-natured pop hits. And then she grew up. “Promise” is a sultry slow jam, its cotton-candy synths Prince-inspired, while the video is all Janet, especially the high-level choreography. The song is gorgeous but jarring next to the rest of her catalog—so much so that she had to leak it herself after an executive called it “the worst R&B record.” We’re just grateful she did. —Dimas Sanfiorenzo

Producer: Jermaine Dupri and Bryan-Michael Cox

Album: J.E. Heartbreak

Label: So So Def/Columbia

If you have a wedding and they don’t play this song, did you even really get married? That’s the level of ubiquity this remix has reached. The original is a soulful love song, but for the remix Jermaine Dupri did a complete 180, creating an anthem that gets people to “report to the dance floor.” The bombastic drums and robotic cadence, taken from Run-DMC’s “It’s Like That,” flip the reception from polite and proper to full-blown party. —Will “ill Will” Lavin

Producers: Rich Harrison and Beyoncé Knowles

Album: Destiny Fulfilled

Label: Columbia/Sony Urban

By the time Destiny’s Child released Destiny Fulfilled in 2004, the group was working in a looser, more self-assured mode, and “Soldier,” the toughest song they ever made, was the clearest example. Over a sparse, bouncing Rich Harrison beat, the song turns Southern slang and swagger into the foundation for a very specific romantic manifesto, with T.I. and Lil Wayne—right before Wayne’s GOAT run—along for the ride. “If his status ain’t hood, I ain’t checking for him” was a funny line, especially with Beyoncé dating Jay-Z as he was gradually transitioning from street-minded rapper into C-suite mogul. —Kia Turner

Producers: Irv Gotti and Chink Santana

Album: Chapter II

Label: Murder Inc./Def Jam

“The Solo Beyoncé: She’s No Ashanti” was the headline on the New York Times review of Dangerously in Love in the summer of 2003. Of course, it gets mocked now. But what gets left out of the jokes is that, at the time, it was kind of true. Ashanti came out the gate a superstar, with a record-setting debut that made her the defining voice of early-2000s R&B.

She’d perfected the Mary J. Blige formula of merging melodic songs about joy and grief with recognizable hip-hop breaks. “Rock wit U (Awww Baby)” flips that formula: the song doesn’t use an old rap classic as its anchor. Instead, it’s carried by Ashanti’s charms. Chink Santana and Irv Gotti give her a breezy, bouncing groove, and the result is pure joy, an unabashed, unpretentious ode to the honeymoon phase. “Rain on Me,” the album’s second single, showed what happens after the honeymoon ends. —Dimas Sanfiorenzo

Producers: Beyoncé Knowles, Tricky Stewart, and The-Dream

Album: I Am... Sasha Fierce

Label: Columbia/Music World

When Beyoncé released “Single Ladies,” the hyperactive, ecstatic anthem that would become her most iconic single, in the fall of 2008, she’d already been married for months; she and Jay-Z had tied the knot in a private ceremony that spring. And yet here she is, slyly flashing her ring on a song about the man who didn’t put one on it. You could write whole volumes about what makes this record special, from the hypnotic production to the breathless vocal performance to that fucking video.

But its most lasting legacy might be the working relationship it established between Beyoncé, The-Dream, and Tricky Stewart, which has become the most fruitful creative partnership of her career—outside of her husband, of course. —Dimas Sanfiorenzo

Producer: Missy Elliott

Album: After the Storm

Label: J

This past summer marked 10 years since the #SoGoneChallenge took over, with Chance the Rapper’s freestyle dedicated to his girlfriend turning it into a phenomenon. Chance’s verse was sweet, a funny twist given how acidic and tough “So Gone” is: it’s about a partner and his cheating ways. On the original, Monica has a verse. Not so sweet. She raps, “Listen, boy, I'm a rowdy chick/Sometimes I have to fight 'cause my mouth too slick.” It’s easy to miss how heated those lyrics are, because Missy Elliott’s production is coy and playful, built around an almost mischievous-sounding flute. —Dimas Sanfiorenzo

Producer: Troy Oliver

Album: The Life

Label: Epic Records/Sony Music Entertainment

Is there a better depiction of love’s transformative power than Ginuwine going from braids to an afro as he ascends through blue-tinted cloud formations, spirit-like, in the video for “Differences”? —Ross Scarano

Producers: Janet Jackson, Jimmy Jam, and Terry Lewis

Album: All for You

Label: Virgin

On 2001’s All for You, Janet Jackson was newly single but not despondent about love. The optimistic “Someone to Call My Lover” pairs America’s “Ventura Highway” guitar with an interpolation of Erik Satie’s “Gymnopédie No. 1.” Somehow, that combination sounds entirely natural beneath Janet, who’s never sounded this romantic.

You can practically hear her smiling. For an artist whose sensuality and aura are so central to her public image, the song’s sunniness is a nice switch. That balance of pop polish and R&B texture is still featured in newer artists like Victoria Monét, Tinashe, and Ravyn Lenae. —Kia Turner

Producer: Jermaine Dupri

Album: Confessions

Label: Arista

“Yeah!” was the smash, Usher hopping on a trendy sound to make something new. But it was also the outlier. Confessions is a storytelling epic, an album that almost works better without the crunk-infused first single.

The follow-up singles are more representative: of course the ballad “Burn,” but the real masterpiece is the audio play that is “Confessions Part II,” strengthened by Usher’s vivid, too-honest storytelling and sputtering production.

For years it was assumed that the song was about Usher’s relationship with Chilli; turns out it came from the diary of its writer and producer, Jermaine Dupri. —Dimas Sanfiorenzo

Producer: R. Kelly

Album: TP-2.com

Label: Jive

After the success of “I Believe I Can Fly,” R. Kelly—demons and all—was emboldened to bring gospel into his singles. On the self-written and -produced “I Wish,” he used it to confront death, remembering his mother, Joann, who died of cancer. The verses are mournful but slightly paranoid: “I wonder how my friends would treat me now, If I wasn't iced up with a Bentley and a house” he sings. While the chorus is hopeful (“I know you're smiling down on me/Saying everything's OK”).

It’s a hood classic, and its outro, with Kelly repeating “come on and braid my hair” over and over, is so unguarded and intimate that it became one of the most memorable moments of his career. —Kia Turner

Producer: Jay Dee

Album: Mama’s Gun

Label: Motown

Sometime around the turn of the millennium, Erykah Badu traveled to Detroit to collaborate with the producer Jay Dee. When she arrived, he asked her to pull a record—any record—from his massive collection. Badu returned with the self-titled album from the obscure jazz-soul collective Tarika Blue. Why? She dug their name. Together, they listened to the opening track, “Dreamflower,” over and over again.

Dilla then looped the bassline, before adding his drums. The result: a dreamy production about reflection and self-discovery anchored by Badu’s bewitching vocals. Though the song never charted, it was nominated for a Grammy and remains a neo-soul classic. —Thomas Golianopoulos

Producer: Dre & Vidal

Album: Chris Brown

Label: Jive Records

There’s a world where you hear what “Yo (Excuse Me Miss)” is about—a young man trying to pick up a random woman on the street—and write it off. But this isn’t a catcall anthem. It’s impossible not to be charmed by teenage CB. The song’s chorus, “excuse me miss,” carries a formality more aligned with Motown than the rap-inspired R&B dominating at the time. Dre & Vidal, the Philly legends behind the boards, lean into that, keeping the backing understated but lush, with ping-pong-sounding drums leading the way. Compared to the club-ready “Run It!,” this is a vocal showcase. There’s a sweetness that hints at his Doublemint gum potential, before things would, you know, go left. —Dimas Sanfiorenzo

Producer: Tricky Stewart

Album: Good Girl Gone Bad

Label: Def Jam/SRP

Early Rihanna was a singer still searching for a sound. But by the time Good Girl Gone Bad arrived, her third album in two years, she’d mostly shed the Caribbean influences she’d been leaning on and gone all-in on expansive, world-conquering pop: big electro synths, arena-rock drums, and even bigger hooks. “Umbrella” was undeniable from the jump.

Hov drops in for a perfunctory verse, but it’s Rihanna who’s the star. Tricky Stewart and The-Dream wrote it with Britney Spears in mind—thank God her team passed. There’s not a soul on the planet who could have sold this song like Rih, whose strained vocals and “eh, eh, eh” refrain turned a great hook into an iconic one. —Dimas Sanfiorenzo

Producer: Rich Harrison

Album: Touch

Label: Columbia

A bit of magic occurs midway through The Meters’ “Oh, Calcutta!”—a back-and-forth between the guitar and the drums that lasts around 10 seconds. Rich Harrison (“Crazy in Love”) lifted the breakdown, added surging drums, go-go rhythms, and even some cowbell, and used it as the foundation for “1 Thing,” Amerie’s soaring, career-defining smash hit for the singer. Fun, sexy, and exciting (despite the chaste lyrics) “1 Thing” is more than a hot beat; Amerie’s feverish vocal performance is just as vital to the song’s success as its funky production. —Thomas Golianopoulos

Producer: Eric Seats and Rapture

Album: Aaliyah

Label: Blackground/Virgin

Of course, there’s a bittersweet nature to “Rock the Boat.” The song is beautiful, but the story behind it is a tragedy. It was the final showcase of her artistry, as she died in a plane crash returning from filming its video. Still, it captures the singer finally unclenching, letting down her cool guard to deliver a record so sensual and sexual that the label was anxious about putting it out. They were obviously being ridiculous. The song is perfect. Her smooth, soothing vocals elevated Static Major’s raunchy songwriting into a sophisticated tropical ballad. —Antonio Johri

Producer: Trackmasters

Album: Backstage: Music Inspired by the Film

Label: Roc-A-Fella/Def Jam

The lasting legacy of “Best of Me, Part 2” is the video: the introduction of the jersey dress, with Mýa rocking a Carolina blue UNC jersey alongside Jay-Z. But really, the song is one of the great R&B remixes of the era. The original “The Best of Me” is modern, with Swizz Beatz providing a jittery contemporary beat, while Jadakiss and Mýa don’t have the greatest chemistry.

“Best of Me, Part 2” features playfully nostalgic production from Trackmasters, paying homage to Biz Markie’s “Make the Music with Your Mouth, Biz.” And it’s a proper duet, with Jay spitting two fleshed-out verses and sharing flirty energy with Mýa. Funny enough, according to Trackmasters, Jay and Mýa did not get along while making the song. Sometimes magic happens in the most unusual circumstances. —Dimas Sanfiorenzo

Producers: Sade and Mike Pela
Album: Lovers Rock
Label: Epic Records

Sade has a way of making songs feel like spells, and “By Your Side” is one of her most enchanting. Lovers Rock wouldn’t be nearly as beloved without its tender opener, which lives somewhere between early-morning pillow talk and late-night reassurance. “You think I’d leave your side, baby? You know me better than that,” Sade softly croons over a lilting, guitar-led bounce, and the promise lands like a warm blanket. Few love songs capture unconditional devotion this plainly. —Jon Barlas

Producer: The Neptunes
Album: 8701
Label: Arista

Before Confessions made his relationship problems everybody’s business, 8701 established how convincingly Usher could play both the heartbroken boyfriend and the man you’d lose your boyfriend over. “U Don’t Have to Call” let him be both. Produced by a peak Neptunes, the record puts his falsetto over a Jetsons-sounding beat that practically demands choreography—specifically in Heelys. —Kia Turner

Producer: Mark Ronson

Album: Back to Black
Label: Island

Written about Blake Fielder-Civil—a man Winehouse would later reunite with and marry—the title track of her sophomore album presents raw heartbreak through the lens of classic soul singers like Aretha Franklin and Dinah Washington. With Mark Ronson at the peak of his powers, the production is mesmerizing, blending smoky tones and a solemn bounce with a funeral-style aesthetic. —Will “ill Will” Lavin

Producer: Stargate
Album: In My Own Words
Label: Def Jam

After building a reputation as one of the sharpest pens in R&B (he’d already written Mario’s No. 1 “Let Me Love You”), Ne-Yo saved his cleverest song for himself. “So Sick” is the most meta R&B song of all time: a sad song about being sick of sad songs, sung by a guy who still can’t bring himself to turn off the radio. Then it became the No. 1 song in the country. The premise reads like a joke, but Ne-Yo is dead serious, or at least really heartbroken”. With “So Sick” it’s all in the details of the songwriting. Is there anything more devastating—or more relatable—than holding on to an ex’s voicemail just so you can still hear their voice? —Dimas Sanfiorenzo

Producer: T-Pain
Album: Epiphany
Label: Konvict Muzik/Nappy Boy/Jive

In the late 2000s, T-Pain was R&B’s favorite drinking partner. Sure there was an ode to female bartenders and getting sloshed with Jamie Foxx but “Buy U a Drank” was the inebriation anthem that kicked it off. Building off Atlanta’s snap music genre and appropriately nabbing hometown hitmaker Yung Joc, T-Pain walked into the club with liquid courage and enough rounds to impress the object of his affection. —Jaelani Turner-Williams

Producers: Beyoncé and Scott Storch

Album: Dangerously in Love

Label: Columbia Records

For years, “Me, Myself and I” disappeared from Beyonce’s live setlists, despite being one of the more successful singles from her solo debut, peaking at No. 4 on the Hot 100 in 2004. A midtempo ode to self-resilience, memorable for its video (you know the bob) and stacked vocal harmonies and runs, “Me, Myself and I” came out of catalog retirement for the Formation tour in 2016, where its lyrics about cheating, loose women, and feeling naive felt freshly autobiographical. It was achingly formidable in the 2000s and by the 2010s it glowed incandescent, self-possessed, and stronger than anyone could have realized. —Ross Scarano

Producer: R. Kelly

Album: Chocolate Factory

Label: Jive

For all of his talents, R. Kelly could be a ridiculous songwriter, with a tendency to run a metaphor down to the cement: the strained vehicle pun of “You Remind Me of Something,” the utopia of “Gotham City,” the soaring-to-new-heights quality of “I Believe I Can Fly.”

And then there’s the “Ignition” remix, a song so stuffed with mashed-together metaphors and lines so corny they sound freestyled (“Sippin' on Coke and rum/ I'm like, ‘So what? I'm drunk’”). It’s a miracle it worked at all. But it did. It was released in October 2002, months after the infamous sex tape surfaced and Kelly was indicted, but he didn’t feel the effects at the time: the song spent five weeks at No. 2 on the Hot 100, finished as the second-biggest song of 2003, and became his last top 5 hit. It had a mini resurgence in the 2010s, and for years it was also his most memorable song. It’s pure carefreeness, with an outro as concise and hypnotic as anything Kelly has ever done.

Like most of his catalog, it’s been tainted by his crimes and convictions. It’s no longer the nightcap that signals the actual nightcap—the last song you’ll hear before the bartender pulls out the dirty rag to wipe down the counter. —Dimas Sanfiorenzo

Producers: The-Dream and Tricky Stewart

Album: Love vs. Money

Label: Radio Killa/Def Jam

If you want to talk about love and desire, you might as well go to the source: Sappho, the ancient Greek poet of whose work we only have pieces. The scholar and poet Anne Carson translated them and has written about their empty spaces—the gulfs between desiring bodies—as fundamental to our understanding and experience of romance. Which brings me to The-Dream’s hit “Rockin’ That Shit,” from the masterpiece Love vs. Money, and its chorus about the unutterable.

“There’s nothing I can say,” he sings over a chorus of triumphant synths that sound like a parade of malfunctioning virtual trumpets. Trick, where you at? He’s somewhere in “the dark,” to use Carson’s language, like all of us. “I don’t think anybody ever knows what another person means when they speak, frankly…. The effort of speaking as a human is the effort to get past that hopelessness with every sentence.” Excuse me while I go cry somewhere in the club. —Ross Scarano

Producers: 7 Aurelius and Irv Gotti

Album: Ashanti

Label: Murder Inc. Records

“Foolish,” the lead single from Ashanti’s 2002 self-titled debut, arrived after her voice had already become familiar through Ja Rule’s “Always on Time” and Fat Joe’s “What’s Luv?” Those guest appearances made her recognizable; “Foolish” made her a star. Built on DeBarge’s “Stay With Me,” a sample already embedded in hip-hop through Biggie’s “One More Chance” remix, the song finds her stuck on a man she knows isn’t good for her. Her sweetness made that frustration believable; she sounded like she was working through it while telling you about it.

While the video flipped the mob classic Goodfellas into a modern R&B story. For all the conversations about Murder Inc.’s role in her success, “Foolish” still makes the clearest case for what Ashanti herself brought to the table. —Kia Turner

Producers: Alicia Keys and Kanye West

Album: The Diary of Alicia Keys

Label: J

Alicia Keys puts on a master class in harnessing unbound yearning with “You Don’t Know My Name.” At 22 years old, the singer turned her emotional angst into a universal language that could be understood by a teenager pining over their first crush or a middle-aged commuter daydreaming about someone they see on their way to work every day but never have the nerve to speak to. I was introduced to this song in all its glory while experiencing the former, and it still slaps to this day. The combination of Keys and Kanye West’s production, the “Let Me Prove My Love to You” sample, and sneaky uncredited John Legend backing vocals makes it more than worthy of being among the best R&B songs of its decade.

Then you add a music video that has now become ubiquitous in R&B circles online—fried fish and hot chocolate, anyone?—and Alicia Keys has successfully made an R&B classic that breathes courage into the hopeless romantics and freaky café customers alike. —Jordan Rose

Producers: D’Angelo & Raphael Saadiq
Album: Voodoo ​​
Label: Virgin/Cheeba Sound

With something this perfect, where do you even start?

“Untitled (How Does It Feel)” is sex in audio form. A raw, hypnotic display of dynamic restraint, it’s an analog edging session anchored by a metronome-like hi-hat and six-count groove, steered by fragile yet heavyweight piano and electric guitar lines that glide like melted butter.

Channeling Prince’s spirit, D’Angelo threads his feathered falsetto in and out of multi-tracked church-choir harmonies before his simmering tension boils over, reaching its climax with a full-throated gospel belt. Then there’s the iconic video. A master class in vulnerable intimacy, it helped seal the song’s legacy and pushed neo-soul (whether you like the term or not) firmly into the mainstream. —Will “ill Will” Lavin

Producers: Mariah Carey, Jermaine Dupri, and Manuel Seal
Album: The Emancipation of Mimi
Label: Island Def Jam

By the mid-2000s, Mariah Carey had long been stamped a legend, but she was in the middle of a nasty cold streak.

Glitter was a full-blown disaster, and its follow-up, Charmbracelet, her first album with Island, fared slightly better but produced no real hits.

And then came “We Belong Together.” Part of it was the novelty: there aren’t many songs by women that are essentially about fumbling a man. And here was Mariah Carey, capital-D diva, begging for a second chance, replaying old conversations, unable to turn on the radio without hearing their songs.

But even at her most vulnerable, she doesn’t sacrifice her vocals. The song has one of the great slow builds in her catalog: what starts as quiet rumination swells into full-throated pleading, closing on what might be her signature high note.

Jermaine Dupri and Manuel Seal deserve credit, too, bringing the smoky, downbeat piano and jittery drums heard all over Confessions and pairing them with storytelling just as vivid. It’s rare for a comeback to double as a career high. —Dimas Sanfiorenzo

Producer: Jermaine Dupri and Bryan-Michael Cox
Album: 8701
Label: Arista

“Ohhhh-oh, no, no, no, no, no, no, no, no, no, no, no, no!” Usher starts the song by wailing into the wind. Then the beat drops, and Usher starts spitting: “When you feel it in your body, you found somebody who / Makes you change your ways like hanging with your crew.”

This is a song about love, but there’s something unhealthy about it. Something sick. “Know you got it bad when you're stuck in the house,” Usher sings. “You don't wanna have fun—it's all you think about.”

The vibe teeters between romance and despair, rooted in anxiety about how all-consuming and potentially life-changing a relationship can be. In the song’s most inspired ad-lib, Usher voices his disgust: “Look at yourself!”

It’s a cautionary tale, but Usher himself is compromised. Jermaine Dupri got the idea for the song after witnessing Usher’s relationship drama first hand. Arguments on the phone with his girl started affecting his focus. During their very first session at Dupri’s new studio, Usher opened up about everything. The song’s co-writer and producer Bryan-Michael Cox remembered it as a “therapy session” that lasted hours.

Jermaine didn’t have all the answers, but he kept repeating one phrase: “Man, you got it bad.”

By the end of that first day, everyone knew that they had something special. “After Usher sang the song, it was kind of like—did we just write the best song of our life?" Cox remembered.

Musically, Jermaine had set out to write a bigger, better version of “Nice & Slow,” Usher’s first number one pop hit. In the late ’90s, “Nice & Slow” was groundbreaking in the way that it injected a rhythmic, rap-influenced singing style into a stripped-down R&B ballad. A ballad with bounce. It was romantic, but you could still rap along to it in the club.

“U Got It Bad” definitely had that bounce, thanks to Dupri’s precise MPC drum programming. But emotionally, it was much more complicated than the gleefully horny “Nice & Slow.” The song’s fractured emotional core comes from an intricate, nylon-string guitar line, played by Bryan-Michael Cox on a keyboard. What starts as an ethereal two-chord vamp suddenly spirals into despair during the chorus, just as the symptoms start piling up. The harmony sinks one step at a time in a gospel-influenced progression that turns desire into obsession.

The emotion boils over on the song’s bridge, during a guitar solo played by session guitarist Billy Odum. In the song’s music video, Usher uses the solo moment to dance his pain away in the rain, spinning on a streetcorner wearing Timberlands and a skully.

Most people assumed the song was about Usher's real-life relationship with TLC's Chilli, who starred in the song's music video, directed by Little X. In the video they play two celebrities in a passionate, messy relationship, struggling to make it work while paparazzi watch. In reality, the song was written before Chilli, and the true identity of his girlfriend at the time has never been revealed. Only Karrine “Superhead” Steffans has spoken publicly about dating him during this era. Usher was out here.

“U Got It Bad” was a number one pop hit for six weeks. It was everywhere, so ubiquitous that it broke Billboard’s all-time record for total radio airplay in a single week. By connecting the singer’s personal life to his songwriting, Dupri opened up a new path for Usher. A few years later, the autobiographical concept album Confessions built on that same idea. That smiling teen idol from the ’90s was suddenly a serious adult artist, working through some shit. —Brendan Frederick