“You never know what to expect with me, man. I do everything. I’m a get it while the getting is good.”

USHER Raymond IV made that proclamation 20 years ago on BET’s , speaking to hosts A.J. Calloway and Free to celebrate the release of his fourth album, Confessions. He was about 26 years old at the time, on the verge of becoming an R&B veteran with a few film and sitcom roles under his belt. But the statement was a harbinger for what would become a decades-long, illustrious career. 

Now, some 30 years after he made his debut, USHER has grown from a gifted-but-indistinguishable teenager into one of the most decorated entertainers of our time. He wears his crown in R&B but has found phenomenal success across other musical genres while making waves in Hollywood and on Broadway. 

After a two-year stretch of 100 consecutive sold-out performances in his sprawling-yet-intimate “My Way” residency that saw him taking his Atlanta-centric show to Las Vegas and Paris, he’s returning to Sin City on February 11 to perform at the Apple Music Super Bowl LVIII Halftime Show at Super Bowl LVIII—an opportunity he hoped for while speaking with BET a year ago. Fans on social media have lobbied for him since his name first started floating around for a performance that will be in front of an estimated 200 million people and then follow the release of his ninth studio album, Coming Home.

USHER began to hone his voice in his church choir in his hometown of Chattanooga, Tennessee, and had a stint with an R&B group at age 10. He and his family moved to Atlanta two years later, and after connecting with A.J. Alexander, who was Bobby Brown’s bodyguard, he landed a performance on the televised talent show Star Search. He later auditioned for LaFace Records cofounder L.A. Reid by singing Boyz II Men’s “End of the Road” and earned a record deal with the label, getting his first official release with the song “Call Me A Mack” on the soundtrack for the cult classic film Poetic Justice. Reid assigned Sean “Puff Daddy” Combs, who had developed Jodeci and Mary J. Blige at Uptown Records, to executive produce his album.

USHER released his self-titled debut at the tender age of 15, a record that even he has admitted didn’t exude much of his own personality or individuality. Combs infused the album with the same sheen that would become his signature sound with his R&B acts at the time, and USHER was singing sexy songs that didn’t reflect his real life. 

Singles like “Can U Get Wit It” and “Think Of You” enjoyed nominal success on Black radio stations, but the album failed to set him apart from his contemporaries, whether they were other child prodigies or more established adult R&B musicians.

Over the next several years, USHER began to establish his own identity. He moved into Jermaine Dupri’s guest room, where he and the legendary producer/songwriter could recreate the magic once sprinkled on Kris Kross, Xscape, Da Brat, Mariah Carey, and Lil Kim, earning Dupri platinum plaques. 

Dupri began to write songs for USHER and encouraged USHER to do the same while supplying him with the sounds that were more in tune with their Atlanta stomping grounds—popping hi-hats, deep 808 bass, and an aesthetic that was more tangential to hip hop.

Once puberty hit, USHER temporarily lost his voice. It caused him to put more work into developing his dance skills to help him become a more multifaceted entertainer, allowing him to walk in the footsteps of his idol, Michael Jackson. 

All his hard work began to crystallize with his sophomore album, My Way, a title he came up with after being enamored by the confidence, elegance, and flair of Frank Sinatra.

USHER was able to sing both sultry slow jams and uptempo, hip-hop-tinged cuts with equal charm. He added spry dance moves to his music videos for songs like the title track and “You Make Me Wanna.” It showed that he wasn’t just performing in the studio; he was developing as a well-rounded entertainer.

It had only been a few years since his first album, but he had grown considerably in the time since, and that maturity was reflected in his unmistakable new confidence. The fans recognized it, too: the single “Nice & Slow” became USHER’s first number one song, and the album landed at No. 4 on the Hot 100 on its way to selling 7 million copies. His stardom in music led to television and movie roles, including Moesha, She’s All That, and The Faculty.

USHER’s output in the early to mid-2000s found him at the birth of an era where he had to reckon with the highs and lows of stardom. His third record, 8701, is the quintessential soundtrack of a 20-something playboy. It's a collection of polished, assured cuts dedicated to womanizing, youth, and having a damn good time.

He reunited with Dupri and worked with famed producers Jimmy Jam and Terry Lewis, Bryan Michael Cox, and The Neptunes for songs that further perfected the winning blueprint that was established on My Way.

His sex symbol status went beyond the music once his relationship with Rozonda “Chilli” Thomas, one third of the multi-platinum group TLC, became public. The album’s singles “U Got It Bad” and “U Remind Me” both went number one; the latter song and “U Don’t Have to Call” each earned consecutive Grammys for Best R&B Vocal Performance in 2002 and 2003, respectively.

On Confessions, however, USHER told a story about the consequences of his promiscuity. The album’s most titular cut, “Confessions Pt. II,” saw him regretfully telling his “fictitious” woman that he had cheated on her and gotten another woman pregnant. Listeners wondered about the veracity behind the lyrics and if he had a side baby on Chilli. Making an appearance to promote the album on BET’s 106 & Park in 2004, A.J. straight up asked him whether or not his confession was real or simply lyrical.

USHER, with nuanced grace, admitted that even though he didn’t have a secret child, the album still reflected parts of his life that really had happened.

“In every album, I’ve been able to tell you a little bit more about myself as well as the way I think. This album was not just for my experiences, but a lot of things that me and the people around me were going through,” USHER responded.

“This idea of making a record about a guy who has to confess to his woman, ‘I got somebody on the side, and by the way, I got her pregnant,’ it’s something that men go through. This album projected real talk. It was about real situations that happen in life. But no, I don’t have a child.”

Confessions became the definitive record not only of USHER’s career but of R&B as a whole for the decade. It went on to sell a diamond-certified 10 million copies, earning a spot as the second-highest-selling album of the 2000s.

The album had four songs that reached number one on the Billboard Hot 100: “Confessions Pt. II,” the inescapable club banger “Yeah!” with Atlanta rap royalty Lil Jon and Ludacris, the painful breakup cut “Burn,” and the lovey-dovey duet “My Boo” with Alicia Keys, which appeared on an expanded edition of the album. USHER also earned three Grammys for that album, out of his eight nominations that year. 

“You have to understand, this is artistic creativity,” he continued on his 106 & Park appearance. “It’s metaphoric ways of explaining situations, as well as realistic situations I’ve been in recently or in the past. I’ve never been able to truly open it all up. You’ve got to get to that point in your career where you can be vulnerable in front of your fans. You’ve gotta keep it real with them.”

That vulnerability continued in the next stage of USHER’s career, although the content was different. He landed a spot on the 2006 Broadway revival of the musical “Chicago,” but only performed for two months before an illness caused his exit. At 29, he was ready to settle down and married Tameka Foster in 2007. The union resulted in the birth of his first two children, Usher Raymond V and Naviyd Raymond.

His following album in 2008, Here I Stand, saw him stepping into adulthood with songs that chronicled his commitment as a husband (“Here I Stand,” “Something Special”) and his hopes as a father (“Prayer For You Interlude”), while still showing his ability to deliver a sexy dance cut with the chart-topping “Love In This Club” featuring Young Jeezy. He got divorced two years later, and in the 2010 album Raymond Vs. Raymond, we saw the demise of that union featured in songs like “Papers.”

USHER also began to create outside of the genre lines of R&B and hip hop, venturing into the EDM territory that had invaded music around that time. He earned another number-one song with the will.i.am-featured “OMG,” which enlisted party-starter Pitbull for “DJ Got Us Fallin’ In Love,” and turned out another one of his signature R&B cuts with “There Goes My Baby,” which earned another Grammy for Best Male R&B Vocal Performance. Looking 4 Myself continued his electronic binge with the Diplo-produced hit “Climax” and the Swedish House Mafia collab “Numb.” 

USHER also took his music industry experience to reality TV for The Voice, serving as a judge and coach for two seasons while competing against Adam Levine, Blake Shelton, and Shakira. He coached the runner-up Michelle Chamuel in 2013’s Season 4 and claimed the winner Josh Kaufman when the show returned for Season 6 in 2014.

His albums in 2016 and 2018 saw him dive further into the rap scene in Atlanta, which had found new life with the melodic, malleable flows of Future and Young Thug, charismatic-yet-deadpan raps by 21 Savage, and dynamic beats by producers Metro Boomin and Zaytoven.

Hard II Love featured two of the aforementioned rappers on the club jams “No Limit” and “Rivals,” and the 2018 album A found Ursh tackling a batch of Zaytoven beats over a week during the sessions for its predecessor. He was knocking on the door of his 40th birthday when he found inspiration in newer sounds and beats, keeping him just as fresh and relevant as some of the artists half his age.

USHER’s last two years have been among the most impressive of his career. He’s created a new archetype for legacy artists. He’s collaborated with younger artists (Yuna, Ella Mai, Summer Walker, to name a few), appeared on NPRseries (watch this), and most importantly, launched his “My Way” residencies. 

Residencies are typically designed as an opportunity for artists to close out decades-long tenures in measured fashion. It allows them to satisfy dedicated adult fans in a relatively low-stakes environment.

Instead, USHER brought an elaborate, star-studded stage show to Las Vegas, starting the residency in 2021 at Caesars Palace and extending it to MGM Grand and then to  he La Seine Musicale in Paris, with over 100 straight sold-out shows through the end of 2023. 

Each show was packed with repeated viral moments, as USHER brought in some of his celebrity friends for guest appearances while serenading celebrity admirers including Keke Palmer, Janelle Monáe and H.E.R. in the audience. When speaking to BET in 2023, USHER said that he had previous stars in mind when putting the residency together.

“Historically, shows like what I'm putting on in Vegas once were a major thing when you think about performers like Sammy Davis Jr. or Lena Horne, or any of the performers that came in that time, back when they couldn't even walk through the casinos that they were performing in because of the segregation law,” USHER said. 

“But now seeing this level of entertainment being put on a pedestal, and not just a residency that's a nightclub, but actually something of expectation, something of value. A sophisticated experience that leaves you [thinking like] ‘Man, that was amazing—those performers, not just that singer singing, the things that they did, the dynamic of the entire night, seeing and feeling as though you were immersed in what the person made you feel that was happening on stage. That's the value of what I'm getting from Las Vegas and what I think I'm offering to my fans.”

The NFL announced USHER’s Super Bowl performance in September 2023, and USHER later shared that he would be releasing his ninth studio album, Coming Home, that same weekend. The record will be a joint release between Mega, a new label USHER co-founded with L.A. Reid, and Gamma, a company founded by former Apple Music executive Larry Jackson.

In an interview with Apple Music, just days before the big event, USHER proudly proclaims he will be the first independent artist to ever perform on the Super Bowl stage. Apple has been following him with cameras from the moment he got the call to the second he steps off the stage for a documentary to be released in the near future.

At 45 years old, he is making the most of every moment, starting with a new North American “Past Present Future” tour debuting in August. Performing goes beyond his blood; it's in his DNA and his uncanny way to solidify this intimate connection with an audience. It's the thing he says is most important to him. He explained it during his interview with Apple Music.

"I’ve tried so many things my entire career, and I’ve just managed to be able to gather people who celebrate my music and celebrate my experiences. And maybe they tie it to theirs. Maybe they got married to a song. Maybe they fell in love to a song. Maybe they made love to a song. Maybe they celebrated and laughed and had an incredible time. Maybe they cried. Maybe they hurt. Maybe had a chance to be confident in a way that they didn’t have before they listened to that song. That’s what R&B has been to me. And I hope that the rest of the world can celebrate in the way I celebrate it."

William E. Ketchum III is a multimedia journalist who covers music, TV/film, pop culture, race, and social justice.