Pop

With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. We’ve already named our Honorable Mentions and our No. 25, No. 24, No. 23, No. 22, No. 21, No. 20, No. 19, No. 18, No. 17, No. 16, No. 15, No. 14, No. 13 and No. 12 stars, and now we remember the century in Usher — a complete-package superstar who’s evolved with the times and amassed one of the century’s most formidable pop and R&B catalogs.

Not many artists can say they’ve made the successful transition from teen sensation to adult superstar. It’s an exclusive club whose membership brings to mind all-time greats like Stevie Wonder, Michael Jackson, Beyoncé, Taylor Swift… and then there’s Usher, baby: the singing, dancing triple-threat in the Braves hat and the U chain. 

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This year, Usher has basically been running on one long career-spanning victory lap, celebrating his 30th anniversary in music and the 20th anniversary of his diamond-certified 2004 classic Confessions, and performing at the Apple Music Super Bowl LVIII Halftime Show in February to the tune of 123 million viewers — the most-watched halftime show ever. And that’s not to say that he’s been stuck in the past either: This February also saw the release of his ninth studio album Coming Home (debuting at No. 2 on the Billboard 200), while in August, he also launched his Past Present Future arena world tour. And all this follows on the heels of Usher’s talk-of-the town My Way – The Vegas Residency that packed both The Colosseum at Caesars Palace in 2021 and the larger Dolby Live at Park MGM a year later – an act he took across the pond with the eight-date Rendez-Vous Á Paris, documented in a concert film released this September. Bottom line: the eight-time Grammy Award winner, who turns 46 on Oct. 14, is riding the wave of one of the most impressive, legacy-cementing comebacks of the last decade.  

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It’s a multigenerational R&B/pop legacy built on nine Billboard Hot 100 No. 1 singles and 18 top 10 singles plus four Billboard 200 No. 1 albums. The latter streak began with the singer-songwriter’s epic 2004 album Confessions, whose nine weeks at the top led to it being crowned the Year-End Billboard 200’s No. 1 album – the same year that his era-defining “Yeah!” team-up with Lil Jon and Ludacris ended up No. 1 on the Year-End Hot 100. But more significant than the history-making chart stats, sales certifications and industry accolades that Usher has racked up along the way is his innate artistry — a crucial key to his staying power.  

There’s his sensual, supple tenor, which easily shape-shifts from crooning balladeer to party jam belter and hits the entire emotional spectrum in between. Equally as arresting are the intricate choreography and smooth footwork that are the hallmarks of his energetic and engaging stage presence. Who else could make rollerskating and singing simultaneously look so cool and easy? Then there’s the music itself: Yes, R&B and pop played the central roles in his career evolution, but the inquisitive music lover has never shied away from experimenting with other genres — dabbling in everything from hip-hop and crunk to EDM and trap, crafting engaging melodies, ear-worm lyrics and hooks you can’t help but sing along with. He’s also been unafraid to reach out to the next generation, linking up over the last several years with younger artists like Chris Brown (“New Flame”), Summer Walker (“Come Thru”), Ella Mai (“Don’t Waste My Time”), H.E.R. (“Risk It All”) and Justin Bieber (the remix to Bieber’s Hot 100-topping hit “Peaches”) — all of whom no doubt also count Usher as a key influence on their own artistry.  

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Usher Raymond IV was just 15 years old himself when LaFace/Arista Records began setting the stage for the precocious newcomer with the 1994 release of his self-titled debut album. Mixing R&B, hip-hop and new jack swing, the album — preceded by puberty claiming Usher’s vocal range at one point — bowed at No. 167 on the Billboard 200. Despite that low entry point, the project still proved to be a buzz-builder, presaging Usher’s first major breakthrough as a singer-songwriter on the cusp of the new millennium: 1997’s My Way.   

At a time when the ‘70s-influenced neo-soul movement — embodied by D’Angelo, Erykah Badu and Maxwell — was making its mainstream ascendance, Usher’s refreshing brand of contemporary R&B was striking a chord with fans by way of its youthful, vibrant take on love, sexuality and burgeoning adulthood. The now-7x-platinum RIAA-certified project spun off three top-two Hot 100 smashes: “You Make Me Wanna…,” “Nice & Slow” (his first No. 1) and “My Way.” 

A year after the millennium’s arrival, Usher catapulted into the upper level of the Billboard 200 with the No. 4 first-week debut of 8701. Initially titled All About U, his third album was delayed from its original 2000 release date thanks to leaks of several tracks, including under-performing first single “Pop Ya Collar.” Collaborating with a bevy of hitmakers — Antonio “L.A.” Reid, Kenneth “Babyface” Edmonds, Jimmy Jam & Terry Lewis, The Neptunes, Jermaine Dupri and Bryan-Michael Cox — the revamped and retitled album (reportedly a reference to the year Usher first performed publicly, 1987, and the album’s Aug. 7, 2001 release date) found Usher delivering a spirited and emotive next-gen take on love and relationships primarily inspired by R&B/soul giants such as Wonder, Jackson, Marvin Gaye and Donny Hathaway.  

Two of the album’s U-titled tracks, “U Remind Me” (the new album’s official first single) and “U Got It Bad” nabbed the top spot on the Hot 100. A third, “U Don’t Have to Call,” reached No. 3. Since certified 5x platinum, 8701 gave Usher his first Grammy for best male R&B vocal performance (“U Remind Me”) plus a second win in that category the following year (“U Don’t Have to Call”). An added plus: fans finally got the chance to experience firsthand the versatile tenor’s falsetto and other vocal riffs plus his agile dance moves when the showman-in-the-making embarked on his first concert outing, 2002’s 44-city 8701 Evolution Tour. 

If 8701 was Usher’s coming-of-age bow, 2004’s Confessions was the coronation of his status as one of the marquee pop artists of the 2000s. Bowing at No. 1 on the Billboard 200 with first-week sales of 1.1 million, the now diamond-certified, career-defining project found the 25-year-old crooner reuniting with Dupri and Cox and Jam & Lewis, sharing deeper experiential musings about love and relationships alongside banging party jams. Chief among the offerings on the dance, pop, hip-hop and crunk-infused album were three Hot 100 No. 1s: the club-ready “Yeah!” with Lil Jon and Ludacris, the yearning “Burn” and the guilt-wracked “Confessions Part II.” Added as a bonus cut to the album’s deluxe edition, the nostalgic love duet “My Boo” with Alicia Keys became Usher’s fourth No. 1 of the calendar year, with fifth single “Caught Up” becoming the set’s final top 10 hit. Confessions later won the Grammy for best contemporary R&B album. Prior to the end of 2004, Usher added yet another top five hit to his arsenal when he and Ludacris reteamed with Lil Jon on the latter’s single “Lovers and Friends.” 

Confessions’ epic success sparked a string of three more Billboard 200 No. 1 albums for Usher, reminiscent of idol Michael Jackson’s No. 1 run beginning with 1982’s Thriller in 1982. Usher’s own run kicked off four years after Confessions with 2008’s Here I Stand. By then a husband and father, Usher ongoing maturation musically and personally was reflected in its six single releases. Those included the synth-layered, Polow da Don-produced lead single “Love in This Club” featuring Young Jeezy (another Hot 100-topper, and the set’s biggest hit) and the Grammy-nominated ballad/title track. Here I Stand was another success, but industry observers noted as well that the album’s double-platinum success paled in comparison to Confessions’ more ee-popping achievements.  

Here I Stand was followed by fellow No. 1 albums Raymond v. Raymond in 2010 and Looking 4 Myself in 2012. The former project, certified 3x platinum and released in the wake of the artist’s divorce from Tameka Foster, included the Hot 100 No. 1 dance-pop single “OMG,” produced by and featuring will.i.am, as well as the R&B hits “Hey Daddy (Daddy’s Home)” and “There Goes My Baby.” Also of note was the song “Papers”: Recorded before the singer filed for divorce, the song was a insightful and vulnerable nod to the personal struggles he was dealing with at the time. The song reached No. 1 on Billboard’s Hot R&B/Hip-Hop Songs chart and peaked at No. 31 on the Hot 100. 

Usher deepened his experimentation into electronic music, with forays into Euro-pop and dubstep, on Looking 4 Myself. His first project for RCA Records boasted the respective top 10 and top 20 hits “Scream” and Grammy winner for best R&B performance “Climax,” co-produced by Diplo. The latter track, an electronic-punctuated slow jam about a tenuous relationship, brought Usher some of his strongest critical acclaim. However, the album – lauded for its alt-R&B vibes in what Usher described as “revolutionary pop” — was his lowest-selling No. 1 entry. At that same time, mainstream R&B was in the midst of shifting away from the pop star hybrid model that Usher symbolized, and moving towards more underground-leaning emerging stars like The Weeknd, Frank Ocean and Miguel. 

The ebb and flow that can accompany any veteran hitmaker’s career trajectory continued for Usher into the mid- to late 2010s. Prior to the 2016 release of his eighth studio album Hard II Love, he released three singles in 2014 — the Grammy-nominated, platinum-certified R&B hit “Good Kisser,” “She Came to Give It to You” featuring Nicki Minaj (a top 20 Rhythmic Airplay hit and the electro/R&B percolator “I Don’t Mind” featuring Juicy J (No. 11 on the Hot 100; No. 1 Hot R&B/Hip-Hop Songs). All three were intended for Hard II Love, but only appeared on the album’s Japanese edition. 

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Leaning back in a more R&B direction, the artist collaborated with songwriter-producers such as Raphael Saadiq, Pop & Oak, The-Dream and Metro Boomin for the resulting Hard II Love. Debuting at No. 5 on the Billboard 200, the album gained the dubious distinction of becoming Usher’s first album to not bow at No. 1 on the Billboard 200 in 12 years, and failed to generate a Hot 100 hit bigger than the No. 32-peaking Young Thug collab “No Limit” (though the song topped R&B/Hip-Hop Airplay, while later single “Missin U” went top 10 on Adult R&B Airplay). Meanwhile, his last North America tour had been 2014’s UR Experience. 

Five years after Hard II Love — with no new full-length releases, aside from his 2018 mini-album A alongside producer Zaytoven — Usher and his team placed their bets on another venture: launching his first Las Vegas residency. The July 2021 gamble paid off in more ways than one: The sold-out My Way tenure wasn’t only an affirmation of Usher’s estimable career, it also doubled as a creative rebirth and introduction to a new generation of fans. Next came the Super Bowl and the ongoing world tour. In between, Usher’s ninth studio album Coming Home arrived — the first release on his indie label Mega, co-founded with L.A. Reid and in association with Larry Jackson’s gamma. Featuring the No. 25 Hot 100 hit “Good Good” and “Risk It All,” the project bowed at No. 2 on the Billboard 200 to become his highest-charting effort in over a decade. 

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Growing up musically and personally in the public eye isn’t an easy feat. But Usher has proven his staying power with aplomb — and an indefatigable outlook. As he told Billboard in August 2021 with his always-disarming smile, “People are critical. But you continue to do it for the love. You do it for the people to connect with what you’re trying to articulate. That pressure is there every time. That’s why I try to give myself as much of a shot as I possibly can by giving fans variety. You’re going to like something.” 

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back next Tuesday as we start to unveil our top 10 artists!