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Might be a touch tasteless to sample Stevie Wonder’s “Living for the City” – a protest odyssey about the plight of being born Black and impoverished in America – for a club jam about an orgy, but what did you expect from a song titled “Lil Freak” anyway? Regardless, Usher can sell sex by barely raising his finger, and Nicki’s cheeky verse manages to seem Sapphic while naming Santa’s reindeer and referencing Everybody Loves Raymond. — JOE LYNCH

When LaFace wanted to make their new baby-faced superstar seem wise beyond his 16 years, they knew to tap the would-be king of rap and R&B, then known as Sean “Puffy” Combs, to oversee his debut product. The opener set the tone with Alex Richbourg (of Trackmasters fame) laying a backdrop that would become Puff’s calling card: sensual R&B perfectly blended with percussion that would shake a club chandelier loose. Usher slides onto the track with hints of the svelte tenor that would strengthen over time and carry him to unprecedented heights. Did anyone believe a kid singing about wanting to make it right for some woman he’s courting? Nah. But we did believe this kid was about to be a star. — DAMIEN SCOTT

“I just wanna take my time.” Sure enough, the eight-minute climax to 2016’s underrated Hard II Love is pretty handily the longest song in Usher’s catalog — an old-school falsetto fest that finds the singer in no particular rush to get where he’s going. “We’re going to a whole ‘nother level,” he insists over heartbeat drums and synths chilly enough to make you wanna cuddle up extra close. Whether or not you’re into it, you have to respect a man who’s willing to put in the effort to properly make the case. — ANDREW UNTERBERGER

“One of his most unappreciated songs”: That comment, found on the song’s YouTube video page, says it all. Given the love-making ballad’s languid drum beat cadence, sultry groove and seductive imagery (“Legs up like a peace sign/ Two cups down, got her tongue-tied/ Can’t wait ’til I’m inside”) laid out by Usher’s inimitable tenor, it’s hard to believe “Peace Sign” didn’t chart. But the sole single from the pair’s album A makes a strong case for revisiting the 2018 collaborative project. — GAIL MITCHELL

The list of career-defining hit records Jimmy Jam and Terry Lewis have made for R&B artists is damn near endless. This 8701 cut didn’t change Usher’s career, but the shimmering promotional single, which finds the star pleading for a love to return to him, cemented that he’s one of our generation’s premiere vocalists — and one of the few stars who could take a song that would have been right at home on New Edition’s Heart Break album from 1988 and turn it into a hit in the futuristic keyboard-dominated radio landscape of 2001. That’s the power of Usher. — D.S.

With a slow grinding rhythm, melisma a’plenty and those robot voices chirping backup on the chorus, the first single from Usher’s debut album – written and produced by DeVante Swing of Jodei – is pure mid ‘90s R&B pleasure. Young Ush was just 15 when this dropped, but with lines like “I might sound a little hasty/ But let’s do what we came to do,” it was clear that LaFace and Arista were tossing out the teen heartthrob playbook and teeing him up to be the R&B sex symbol of the millennial generation. — J. Lynch

Usher’s 2015 collaboration with Martin Garrix is an overlooked but catchy moment from his dance-club banger period. Garrix softens his progressive house edge with pop-friendly, guitar-backed verses, where Usher’s passionate vocals capture the palpable intensity of falling for someone and hoping the feelings are mutual. His “Oh-oh-oh-oh” build-up to the happy-go-lucky xylophone beat drop gives listeners the ultimate high, fitting for a song loosely about defying gravity (“Up this high, we’ll never hit the ground,” Usher belts in the chorus). — HERAN MAMO

Although the metaphors aren’t too subtle on this standout Looking 4 Myself sex jam — the chorus starts with the line “It’s raining inside your bed,” after all — Usher commits to the double entendres and sounds spiritually enlightened above the hazy guitar and echoed drums. “Dive” demonstrates a combination of Ursh’s technical skill (listen to how his falsetto crescendoes within the word “precipitate”) and arena-ready power (lighters up when he hits that titular word!). — J. Lipshutz

Throughout this understated, Babyface-helmed My Way deep cut, a young Usher (just 19-years-old!) lays the foundation for his career as an eternal leading man, but the flashes of youth in his voice provide an energy of innocence that pairs well with the chaste lyrics. In fact, he doesn’t really get PG-13 until that heated sigh before he croons, “I’ll freak you wherever you want.” Nonetheless, it’s the bridge – with backing vocals from ’90s hitmaker Shanice, engaging in a conversational call-and-response with Ush – that makes it clear the mid-tempo “Bedtime” is more about the concept of yearning than actually yearning for a specific woman. Either way, who can resist those perfectly placed ad-libs? — KYLE DENIS

Thank goodness someone understood that we needed this beautiful duet featured on The Color Purple‘s soundtrack. The seamless fusion of the pair’s smooth, buttery vocals calls to mind such soulful R&B pairings as Ashford & Simpson and Roberta Flack & Donny Hathaway. But Usher & H.E.R. bring a contemporary take to this empowering song about perseverance and strength, which the latter produced and co-wrote. Of his first time working with H.E.R., Usher recently told Billboard, “Our friendship led us to this remarkable song.” — G.M.

Usher didn’t exactly make it easy for audiences to love Hard II Love, an album filled with few obvious singles but plenty of the least-intuitive (and most-rewarding jams) of his career. Take “Missin U,” which deploys one of R&B’s most classic can’t-miss song titles for a midtempo puzzler that’s lurching trap on the verses and shuffling jazz on the chorus, with a lyric about being wistful for a future relationship (“I reminisce of all of the things that don’t exist yet/ Like the breakfast on Sunday mornings after drunk sex”). Like the album’s cracked-sculpture cover, it shouldn’t work; unlike the cover, it actually does. — A.U.

Though Usher’s Here I Stand wasn’t quite the commercial haymaker that Confessions was, his fifth studio album possessed high-caliber deep cuts highlighting his evolution from avid club-goer to devoted then-husband. “Best Thing” was the song that best exemplified Usher’s growth, showing him abandoning his player ways after stumbling on a goldmine in the romance department. “No more trickin’ and kissin’,” vows the changed singer. With a guest Jay-Z in his corner, Raymond’s leap at love lands successfully. — CARL LAMARRE

Oozing with grown and sexy vibes, “Twork It Out” was an 8701 slow burner. Though Netflix-and-chill wasn’t quite in during the early 2000s, Usher cajoles his lady with a fun-filled date night at the house. With Jimmy Jam and Terry Lewis helming the production, Usher sets the mood with rose petals, bedroom theatrics and dulcet vocals, which are more than enough to woo his partner out of her clothes. — C.L.

Before “Hey Daddy” became a trending TikTok sound for Gen Z to make memes with, the song served as the lead single from Usher’s sixth studio album, and his proclamation of a full-throttle Lothario era. Giving himself the title of “daddy,” Usher floats over Rico Love and The Runner’s sleek combination of twinkling synths and handclaps as he croons sweet promises of sexual escapades to a gaggle of female backing vocalists. They’re the ones that truly give the song its dynamism, but between the big belt and flashy ad-libs in the final chorus, “Hey Daddy” goes heavy on the bombast. — K.D.

Usher’s R&B stylings have crossed into the pop world plenty of times, but never before with the zippy, new wave-adjacent textures of “Looking 4 Myself,” the buoyant self-exploration that inspired the title of his 2012 album. Although featured artist Luke Steele, one-half of Empire of the Sun, only chimes in with some limited post-chorus rejoinders, the influence of the Australian electro-pop duo on the song is undeniable, as Usher injects the metallic pop-rock with some sleekly delivered soul. — J. Lipshutz

Summer Walker honored her ATL hometown hero by lifting his 1997 Hot 100 No. 2 hit “You Make Me Wanna…” for her arousing Over It single “Come Thru.” The original acoustic guitar melody and atmospheric hi-hats give the modern hook-up jam a nostalgic feel, but rather than finding herself stuck in the middle of a love triangle, Summer is debating if her collaborator is worth dropping the rest of her roster for. “Yeah, you got somebody, I been in this predicament,” Usher croons as a nod to his classic, which has proven its influence on the modern generation of R&B superstars. — H.M.

What a difference puberty makes. Although it dropped just 11 months before “Can U Get Wit It,” “Call Me a Mack” finds a 14-year-old Usher Raymond IV sounding very much like a little kid playing dress-up in his older brother’s new jack swing blazer. Even so, Usher’s vocal abilities and easy-going charisma are abundantly clear — and the fact that his debut single hailed from the classic Janet/Tupac flick Poetic Justice tipped to the fact that this “Mack” attack wasn’t a feint. — J. Lynch

Can a song make you fall in love? This 2010 top five Hot 100 hit probably soundtracked its fair share of dancefloor meet-cutes thanks to Usher’s lyrical pickup lines (“Ain’t I seen you before? I think I remember those eyes, eyes, EYES…”). The real love story here might be how well the R&B star’s falsetto marries with the thumping Europop beat, crafted by Swedish hitmakers Max Martin and Shellback – or the magnetic pull a DJ can have over a club packed with sweaty partygoers when just the right track plays. Or maybe it’s just the perfect match of a Pitbull verse with an early 2010s dance-pop hit. Whatever the case, it was love at first play. – KATIE ATKINSON

A non-album single whose falsetto’d hook and woozy electro-pop buzz made it feel like an unofficial sequel to “Climax,” “Crash” has the same kind of nervy romantic panic as its predecessor, but there’s a warmth and an excitement to its falsetto hook and synth throbs. Usher still realizes that his relationship is destined for wreckage, but he’s still smiling remembering the ride: “I’m not thinking ’bout nobody else but you/ You’re the only one who takes me there.” Not as dramatic, but just as visceral. — A.U.

“I love love, I’m just bad at it,” Usher admits — sorta indirectly summarizing the first 25 years of his recording output. Co-written by recent song of the year Grammy winner Theron Thoms, the sparkling “Bad Habits” shows Ush in his most natural mode: somewhere between a good guy dragged down by his worst impulses and a bad guy really trying to do better. Few can play halfway between the hero and the heel as well as Usher, and the song’s sweetly retro electro-R&B production (including a comforting “Computer Love” sample 2/3 through) always has sympathy for him, even when we don’t. — A.U.

Fresh off the success of Justin Timberlake’s FutureSex/LoveSounds, Danja, the Viriginia Beach producer who co-produced the album with Timbaland was in extremely high demand. It was a given he would link up with biggest R&B star in the world. Featured on the follow-up to Usher’s watershed Confessions album, Here I Stand, “Appetite” finds Ursh fighting the temptation to step out on his lady while on the road. The beat is all fluttering space synths and twirling woodwinds, and Usher gives an admirable vocal performance. It’s just slightly unbelievable to imagine someone as famous picking up women in the ways described on the song: “My Mac is in my backpack, I’m surfing all the sites,” he sings. But, hey, anything’s possible. — D.S.

Seven months prior to the September 2016 release of Hard II Love, Usher guested on this gold-certified lead single from the Malaysian singer-songwriter and Pharrell protege’s Chapters album. The ballad’s subtle spareness perfectly showcases Yuna and Usher’s soft vocals as they tenderly emote the thrill and angst that come with crushes. The gem of a duet peaked at No. 3 on Billboard’s Adult R&B chart. — G.M.

Another Raymond v. Raymond single, “There Goes My Baby” is one of the crown jewels of Usher’s second decade – specifically when it comes to brilliant vocal showcases. From his seductive tone to his expansive range, Usher has long been one of the most celebrated male vocalists in R&B. On “Baby,” Usher resides almost exclusively in his falsetto, his warm, honeyed too cooing of a love that hurts him no matter how much he believes it. Rico Love and Jim Jonsin pair Usher’s stunning vocal with production that plays on his EDM forays – check out those background synths – with on-the-nose handclaps that complement the charming sappiness of the song’s lyrics. — K.D.

Before Usher and Monica were R&B icons, they were barely out of their teens, recording some of the most soulful slow jams of the late ‘90s. No, the title isn’t a bait and switch: “Slow Jam” literally finds the two A-Town heroes pleading with a DJ to play another such ballad so they can dance with their lover – a phenomenon that may seem a bit foreign to younger audiences who are encountering Usher’s 2024 Super Bowl Halftime Show through tracks like “Good Good.” Despite their youth, both singers deliver vocal performances with finesse far beyond their years, harmonizing and trading off ad-libs across the guitar-forward track — but it’s the way they both subconsciously employ a bit of gospel-rooted grit to lift the bridge to its climax that truly impresses. — K.D.

Buried deep in the Confessions’ treasure chest lies arguably one of Usher’s most underrated songs, “Can U Handle It?” The singer is in peak-tease mode, pondering where his lady can match his wits in the bedroom. Testing her limits, the singer darts the simple question, “Can you handle It?” In response, his lover replies with aplomb over the prodding soul groove, proving that she’s willing to rev the temperature and meet his expectations. — C.L.

The most divisive song in Usher’s catalog continues to split fans a decade and a half later: Is it Usher’s cringiest attempt at trend-hopping, or simply his greatest stadium anthem? Why not both: “OMG” is certainly 2010 enough to give you The Decision flashbacks, with copious Auto-Tune and EDM black-light production and will.i.am-penned lyrics about booties and boobies — but Usher sells the vocal, the beat stop-starts are charming and the Jock Jams chant-along hook is irresistible. It’s OK to think that it’s his dumbest song ever, and also that it’d be a travesty if he didn’t play it at the Super Bowl. — A.U.

Built around an absolutely blistering sample of Dionne Warrick’s “You’re Gonna Miss Me” — so prominent in the mix that Usher actually responds to its taunting in the intro (“That’s the last words she said to me”) — “Throwback” was one of the signature non-singles from Confessions, getting considerable R&B radio airplay even as an album cut. Usher’s frenzied belting about his searing regret matches the intensity of the Just Blaze-helmed beat, and Jadakiss’ tears-on-his-pillow guest verse takes the late-night panic to the next level. Call it “Confessions, Pt. III: Too Little, Too Late.” — A.U.

A 2014 single that topped out at No. 65 on the Hot 100 and was never included on a proper album, “Good Kisser” could be accused of brandishing too many hooks — from the all-falsetto rhymes in the verses to the “devil is a LIE!” transition to the funk riff that snakes throughout the track — and that’s all before the actual chorus. Yet Usher is too smooth to ever make “Kisser” sound overstuffed, hopscotching across the song’s rhythmic segments and making sure each receives the full blast of his charisma. — J. Lipshutz

After hopping on the remix of Alicia Keys’ “If I Ain’t Got You” six months earlier, Usher reunited with the red-hot R&B star for a proper duet. The two portray exes who reminisce about their past but still devotedly declare each other as “my boo.” And their soaring harmonies on the “My oh, my oh, my oh, my oh, my boo-ooo-oooo” post-chorus seal the deal that they’re forever meant to be. While it was released on the expanded edition of Confessions, “My Boo” continued the No. 1 streak of the album’s three previous singles, spending six weeks of its own atop the Hot 100. — H.M. 

In what could have easily been another 8701 top 40 scorcher if it had been released as a proper single, the Diddy-assisted “I Don’t Know” had party-starter written all over it. Produced by The Neptunes, the nimble singer is aching for a night out with the boys and refuses to hit pause for anyone. With the dancefloor being his domain, Usher reigns supreme in what rightly should have served as the club-conquering sequel to the album’s “U Don’t Have to Call.” — C.L.

For Usher’s second full-length effort, Jermaine Dupri took over EP duties and kicked off what would be a long and fruitful partnership. One of the most successful products of that ‘ship was the title track of Usher’s sophomore album, “My Way”: Seesawing between lustrous singing and hard-edged syncopated singing and rapping, Usher showcases the full suite of his talent, vocally traipsing around the pulsating bassline. When you factor in the memorable music video, which made Usher the premier dancing solo star of his era, it wasn’t a surprise when the the JD-produced single became a megahit, peaking at No. 2 on the Hot 100. — D.S.

Following in the loverboy footsteps of LL Cool J’s “I Need Love,” this Diddy number signals that it’s a rap hit for the ladies by enlisting Usher’s silky vocals and yearning ad libs (and a gratuitous ab-revealing shirt lift in the music video for good measure). Usher’s magic is sprinkled all throughout the No. 2-peaking Hot 100 smash, like when Loon raps “I need somebody I can chill with” and Usher sweetly croons in the background “Let’s chilllll,” or after Diddy confesses he wishes a woman would’ve had his child and Usher whisper-sings “Girl, you mean that much to meeee.” Basically, he brings the heart to what could have felt like a bro-fest. – K.A.

One of Usher’s best qualities is how seamlessly he clicks with virtually every one of his female collaborators – and Ella Mai is no different. Linking up with the dream team of Bryan-Michael Cox and Jermaine Dupri for this 2019 single, Usher and Ella match each other’s forward, hit-it-and-quit-it energy. The “Boo’d Up” singer injects her tone with the perfect amount of sass to balance Usher’s calm – and borderline cocky – cool. Pulling inspiration from tracks such as The Jacksons’ late-’70s Philly soul hit “Show You the Way to Go,” this duet is perfectly primed for a two-step – down to the sultry synergy between the thumping bass and grandiose strings. — K.D.

“Without You” wonderfully blends two of Usher’s strengths: heart-wrenching ballads and lighthearted bangers. Usher describes in painstaking detail how paralyzing it feels to be without the one who means absolutely everything to him. But Guetta’s kaleidoscopic beat drop creates a moment of pure bliss, encouraging listeners to throw their hands up in the air with the hope that they’ll never have to know the desolate life they so greatly dread. Usher effortlessly pulls off the spirited “Oh-oh-oh” chant in the chorus and the mellifluous “Without you-u-u-uu-uuu” outro, further demonstrating why he’s the perfect artist for this crossover collaboration. — H.M.

The fifth and final single from Confessions is the only one that didn’t top the Hot 100, but it was still a top 10 hit that helped define what uptempo R&B meant in the mid ‘00s. Over a syncopated beat and woozy synths from producers Dre & Vidal, Usher’s voice oozes confusion and longing as he spins a tale of the hunter becoming the prey. And like the best Usher songs, it has that one vocal moment — the repeated “caught UP!” refrain – that is likely to intrusively echo in your head anytime you hear those words IRL. — J. Lynch

“Love In This Club,” a No. 1 smash for Usher in 2008, stands as a bleary-eyed ode to getting a little too frisky on the dance floor; its remix, which swaps out Jeezy for Beyoncé and Lil Wayne, is more opulent and thoughtful, with Ursh’s sexual declarations turned into a sultry dialogue with Queen Bey and the hook re-fashioned into a more open-hearted yelp. Any remix is going to benefit from a Beyoncé guest spot; ditto for Lil Wayne, in the middle of his mixtape-fueled ascent here and rapping about neck-kissing, before referencing his just-released single “Lollipop.” — J. Lipshutz

Ending a romantic relationship is never easy, and that’s why Usher goes straight to the heart of the matter in the first verse of this searing breakup classic. “I do, but you don’t, think it’s best we go our separate ways …/ When I’m hurtin’, baby, I ain’t happy, baby…/ I think that you should let it burn,” he sings plaintively — though he later has second thoughts about his decision (“I don’t know what I’m gonna do without my boo”). Produced by Jermaine Dupri, who co-wrote with Usher and Bryan-Michael Cox, “Burn” is the second Hot 100 No. 1 hit from the trio’s monumental Confessions album, and peaks with one of the most memorable climaxes of his career: “Too many days, so many hours, I’m still burning till you returrrrnnn!” — G.M.

Set off by a blazing guitar lick and a booming drum clap, “Bad Girl” detonates about 2/3 of the way through Usher’s 2004 blockbuster, letting you know there’s gonna be no dragging in the album’s back end. “What y’all know about a supermodel?/ Fresh out of Elle magazine,” Ush asks in taunting falsetto, silently providing the answer: Not as much as I do. Of course, Confessions was so loaded with hits that “Bad Girl” never got official single release, but the thing was too cold to not get some additional exposure — so Usher cleverly used it as a fakeout at the beginning of the “My Boo” video, with its lascivious funk groove making for the perfect contrast to the sentimental ballad that followed. — A.U.

It’s hard to explain just how dominant “New Flame” was back in 2014, even outside of its notable chart success — it’s truly a “if you know, you know” situation. This link-up with Chris Brown and Rick Ross was something of a royal hat trick; what appeared to be a “passing the crown” moment, was actually Usher sonning Brown on his own song. Over Count Justice’s thumping electro-R&B beat the two trade verses about the allure and thrill of starting a new relationship. While Brown puts on a strong performance, there’s an air of effortlessness to Usher’s vocal that is simply enrapturing, soaring whenever he takes the upper harmony, but he also tasteful and understated when appropriate. Perhaps the best part of “New Flame” is the way Usher took the track as another opportunity to delve into a more mature lane of his decades-long exploration of the various winding avenues of love. — K.D.

This is the one that taught everyone Usher’s full name – and how to spell it. There are so many highlights from Usher’s first Hot 100 No. 1 hit, including that time-specific opening line (“It’s 7 o’clock on the dot”), the unexpected rap breakdown (“They call me U-S-H-E-R R-A-Y-M-O-N-D”) and that braggadocious bridge (“I’ll freak you right, I will”). But what this song really accomplished was selling the baby-faced 18-year-old as an honest-to-god sex symbol, with its sultry guitar-plucking production and suggestive lyrics. – K.A.

“Please tell your lovers and friends/ That Ursher, Jon and Luda had to do it again.” So explains Ludacris in the outro of “Lovers and Friends,” the blockbuster sequel to their monster hit “Yeah!” from earlier in 2004; neither lovers nor friends could have anticipated that Luda, Usher and Lil Jon would follow up that danceable pop-rap smash with an emotionally vulnerable slow jam, but kudos to that ATL trio for understanding that a reunion couldn’t function as a rehash. Divorced from its context as a second installment, “Lovers and Friends” remains a warm, swaying R&B summit all these years later, with Usher’s vocals understandably leading the conversation, and Lil Jon’s production maintaining a lightness and care that simply could not have been expected when “Lovers and Friends” appeared on his Crunk Juice album. — J. Lipshutz

We all know and love that opening riff, and regardless of the rest of the world’s best efforts, only Usher can make it sound like *that*. But “Superstar” is a stunner beyond its slinky opening. If “Superstar” is proof of anything, it’s that Usher ascended to R&B’s highest heights by fashioning himself as a multidimensional artist. Sure, he can pack on bravado and sexual innuendo when he wants to, but he can also become completely selfless in the name of love: “Front row, there I am/ Jumpin’ and hollerin’, wavin’ both hands/ Would you notice me, little me?” he pleads. With a combination of an incredibly earnest vocal performance that leans into the innate schmaltz of submitting to love, and a guitar-anchored instrumental that exudes all the seductive qualities of a top-shelf slow jam, “Superstar” is an absolute gem. — K.D.

The hype train for 8701 began when Usher released the album’s lead single, “U Remind Me.” Produced by Jimmy Jam and Terry Lewis, Usher’s having a bad case of the double take after a nasty break-up –every girl he meets oddly reminds him of his ex-girlfriend. While the cheeky lyrics and playful video added more sheen to the already-polished song, Usher’s vocal performance is the show’s star: The bridge finds the R&B dynamo proving why he’s more than a dancer, hitting high notes with seamless breath control. “U Remind Me” would be the catalyst in Usher’s journey back to the Hot 100 mountaintop, as the summertime head-bopper became his second No. 1 in July 2001. — C.L.

Usher found breakout success with this ode to another woman, professing his love to a friend while in a relationship with someone else. What should he do? He talks through all the options in the Jermaine Dupri-produced Hot 100 No. 2 hit (which once again makes perfect use of a plucky acoustic guitar) and somehow makes us sympathize with his predicament when the obvious answer is right there in the song: yes, he should tell his baby, “bye-bye.” But that’s not the point here; the point is that Usher and JD landed on the perfect showcase for the young R&B singer: confident and cool, a little naughty but mostly nice, and, most importantly, 100% authentic. This is the Usher we came to know and love, and it all really started right here. – K.A.