At age ten, Usher joined an R&B local quintet called the NuBeginnings, which was organized by local music promoter Darryl Wheeler. Usher recorded ten songs with the group in 1991, and the ensuing album, Nubeginning Featuring Usher Raymond IV, was only made available regionally and by mail order. However, Patton took him out because, according to her, it was a “bad experience”. The album was re-released nationally in April 2002 by Hip-O Records.

At age 13, Usher met A.J. Alexander at a local talent show in Atlanta. Alexander, who at the time was Bobby Brown’s bodyguard, would take Usher around and have him perform in parking lots and talent shows. Alexander invited Bryant Reid, an A&R representative from LaFace Records to see Usher perform on the television talent show Star Search. Following the performance, he arranged an audition for Usher with L.A. Reid, the co-founder of LaFace; Reid signed Usher on the spot to a contract with the record company after Usher sang Boyz II Men hit record “End of the Road”. Usher’s mother left her job as a medical technician to manage his career. Usher was introduced to the public on “Call Me a Mack”, a song he recorded for the soundtrack album to the 1993 drama-romance film Poetic Justice. During this time period, the young Usher first met Chilli of TLC, his label-mate whom he would later date.

Preparing for his debut album, Usher lost his voice. Usher was going through puberty and had a difficult time adjusting his voice. LA Reid became skeptical of Usher and put his album on hold; he thought about dropping him from the label. Usher pleaded with the label to keep him and they did. From this point Reid didn’t know what to do with Usher so he sent him to New York in the spring of 1994 to live with record executive Puff Daddy to “attend” what Reid called “Flavor Camp”. Usher quickly adapted to the lavish lifestyle of Puff Daddy although in an interview with Rolling Stone, he described this period as the “hardest days” of his life. “I had to knuckle up, figure shit out in New York” he said.

On August 30, 1994, LaFace released Usher’s self-titled debut album behind the co-executive production of Sean “P Diddy” Combs. Usher peaked at number twenty-five on the Billboard Top R&B/Hip-Hop Albums chart and was accompanied by three singles: “Can U Get wit It”, “Think of You”, and “The Many Ways”. The album has sold over 500,000 copies, to date. The album received backlash because Usher was singing about sex, and him only being 15 years old, the public had a difficult time believing that this was so. Again LaFace had their reservations about signing Usher because the album wasn’t as successful as they anticipated. At this time Usher’s mother took control of his career and put him in more talent shows the summer of 1995 building Usher a larger fan base and ultimately giving L.A. Reid more confidence in Usher.

After graduating from high school, Usher continued to develop his skills as a stage performer and laid the groundwork for his second album. He also appeared on LaFace’s version of “Let’s Straighten It Out”, a 1995 duet with fellow Atlanta teen recording artist Monica; and on “Dreamin'”, from LaFace’s 1996 Olympic Games benefit album Rhythm of the Games. He was also featured on “I Swear I’m In Love” off the soundtrack to the 1996 film Kazaam.

Usher developed a friendship with American record producer Jermaine Dupri, with whom he co-wrote and produced several tracks for his second album, My Way, released on September 16, 1997. The album’s lead single, “You Make Me Wanna…”, reached number one in the United Kingdom, becoming Usher’s first record to be top single; this resulted in him increasing in popularity. It also became Usher’s first gold- and platinum-certified single in the United States. The album’s second single, “Nice & Slow”, peaked in January 1998 at number one on the Billboard Hot 100, giving Usher his first US number-one single. In February of the same year, the single was certified platinum by the RIAA. My Way has been certified six-time platinum in the United States.

“You Make Me Wanna…” won the Best Male R&B/Soul Single at the 1999 Soul Train Music Awards. In the closing months of 1997, Usher embarked on a series of tour engagements including a spot on Puffy’s No Way Out tour, dates with Mary J. Blige, and the opening spot on Janet Jackson’s The Velvet Rope Tour. Usher’s first concert album, Live, was released in 1999, which featured appearances by Lil’ Kim, Jagged Edge, Trey Lorenz, Shanice, Twista and Manuel Seal; the album has been certified gold in the United States.

Usher made his acting debut on the UPN television series Moesha, which resulted in a recurring role on the series and subsequently his first film role in 1998’s The Faculty. Usher’s extracurricular activities outside of the recording industry gathered momentum over the following year, as he was cast in the soap opera The Bold and the Beautiful. He completed two more films, She’s All That, and his first starring role in Light It Up. He also appeared in the Disney TV movie Geppetto.

Usher’s third studio album, originally titled All About U, was stated to be released in early 2001. The first single, “Pop Ya Collar”, was released in late 2000 and became a number two hit in the UK but underperformed in the United States. The album was subsequently pushed back and retooled after select tracks were later leaked to the radio and Internet. After having revised and renamed to 8701, the album was released on August 7, 2001 (8.7.01). The first two singles “U Remind Me” and “U Got It Bad” each topped the Billboard Hot 100 for four and six weeks, respectively. 8701 has been certified four-time platinum in the United States.

Usher appeared in the 2001 film Texas Rangers. In February 2002, Usher won a Grammy for Best Male R&B Vocal Performance for “U Remind Me”. The next year, he won the same award for “U Don’t Have to Call”, making Usher the only artist aside from Luther Vandross and Stevie Wonder to win this award consecutively. In the summer of 2002, Usher contributed vocals to P. Diddy’s “I Need a Girl, Part I”. The year closed out with a trio of TV series appearances, all in November, on The Twilight Zone, 7th Heaven, Moesha, and American Dreams, the latter in which Usher portrayed Marvin Gaye.

Usher’s fourth studio album, Confessions, was released on March 23, 2004—just as its first single, “Yeah!”, was in its sixth week at number one on the Billboard Hot 100 and fifth week on top of the Hot R&B/Hip-Hop Singles Chart. The album’s nearly 1.1 million unit debut sales was the highest first-week numbers ever scanned by a male R&B artist and the seventh best of the Nielsen SoundScan history. The album has since sold over 15 million copies worldwide, with over 10 million in the United States, earning the album a Diamond certification by the RIAA.

The album’s second and third singles, “Burn” and “Confessions Part II”, also topped the Billboard Hot 100, the former for eight weeks. Usher became the first artist to top the Billboard Hot 100 Airplay with four consecutive number-one singles, In September 2004, “My Boo”, a duet with American singer-songwriter Alicia Keys, also peaked at number one at the Billboard Hot 100, becoming the album’s fourth number-one single. In December, the album’s final single “Caught Up” peaked at number eight on the Hot 100.

Confessions earned Usher numerous awards, including four American Music Awards, two MTV Europe Music Awards, two MTV Video Music Awards, and three World Music Awards. At the 47th annual Grammy Awards ceremony in 2005, Usher won three awards, including: R&B Performance by a Duo or Group With Vocals for “My Boo”, which he shared with Keys; Rap/Sung Collaboration for “Yeah!”; and Contemporary R&B Album for Confessions. At the 2004 Billboard Music Awards, Usher was recognized Artist of the Year, in addition to receiving 10 other accolades.

Usher supported Confessions with “The Truth Tour”. The tour set featured a small stage up on top of the main stage, where the band played with Usher and his supporting dancers left with enough room to perform. The smaller stage had a mini platform attached to it which lowered to the main stage and had two big staircases on both sides of it. To the left, a group of circular staircases climbed to the top, and to the right, there was a fire escape replete with steps and an elevator. Kanye West and Christina Milian were the opening acts for the tour. Usher at select dates would bring out a special guest, during his Atlanta show taping he brought out his artist at the time Rico Love to rap a verse on the song “Throwback”. During a more intimate part of the show, Usher’s dancers selected singer Monica from the crowd to be serenaded by Usher while he sang album favorites “Do it to Me” and “Superstar”. Usher also performed the Confessions Pt. II remix, where Kanye West would appear from back of the stage. Then lastly Usher would also bring out artist Lil Jon and Ludacris where they would finish the show performing the hit “Yeah”. This concert date was filmed to make the official tour DVD of Truth Tour: Behind the Truth “Live from Atlanta”. It has been certified by the RIAA selling more than 7 Million copies.

In the spring of 2005, Usher scored a number three Hot 100 hit as a featured vocalist on Lil Jon’s “Lovers & Friends”. In 2007, Usher also collaborated with R. Kelly on the track “Same Girl”, for Kelly’s album Double Up. He was also featured in a remix version of Omarion’s “Ice Box”. Usher also appeared on the track “Shake Down” on American singer-songwriter Mary J. Blige’s 2007 album Growing Pains. According to Robert Hilburn of Los Angeles Times, Usher was voted number-one on the executive voting based “Pop’s Power List” and described as a “sure-fire property”. In November 2005, Usher starred as a disc jockey named Darrell in the Lions Gate film In the Mix.

On August 22, 2006, Usher took over the role of Billy Flynn in the long-running Broadway revival of the musical Chicago. Usher’s opening night brought out stars Penélope Cruz, Gabrielle Union, Clive Davis, and Rosie Perez among others. Usher played the role of Flynn for two months but a case of strep throat brought an abrupt ending to Usher’s run in Chicago, which saw a spike in ticket sales after he joined the cast. The New York Post reports that Usher’s absence cost the production an estimated $400,000 in refunds to disappointed ticket buyers. The producer of Chicago, Barry Weissler, issued a statement sending his “thoughts and best wishes to Usher for a quick and speedy recovery. Usher made a spectacular Broadway debut, bringing a great dedication, work ethic and his amazing talent to the show. We all hope that he might return at some point for the many fans that were unable to see his wonderful performance as Billy Flynn. Usher has found a new home on Broadway and is welcomed back anytime.”

Here I Stand was released on May 26 in the United Kingdom and May 27, 2008 in the United States. The album debuted at No. 1 on the Billboard 200 Chart with first-week sales of over 433,000 copies. To date Here I Stand has sold over 1.5 million copies in the United States, been certified platinum by the RIAA, and has sold over 5 million copies worldwide. While not approaching the success of his previous album, it received positive reviews from most music critics, who praised the maturity in the album’s lyrics. To promote Usher’s fifth studio album, the single “Love In This Club” was sent to radio in February 2008 and peaked at number one on the Billboard Hot 100. It went on to spend three consecutive weeks at the top—becoming Usher’s eighth number-one single and the fastest-rising song of his career. It also reached No. 1 on the Hot R&B/Hip-Hop Songs chart. The single was another huge international success for Usher. It reached No. 1 on the New Zealand Singles Chart, No. 3 on the Irish Singles Chart, No. 3 on the Eurochart Hot 100, No. 4 on the UK Singles Chart, No. 5 on the Japan Hot 100, No. 5 on the German Singles Chart, No. 5 on the Belgian Singles Chart (Flanders), No. 6 on the Canadian Hot 100, No. 8 on the Swedish Singles Chart, No. 8 on the Australian Singles Chart, No. 9 on the French Singles Chart, No. 9 on the Swiss Singles Chart, No. 10 on the Norwegian Singles Chart, No. 12 on the Austrian Singles Chart, No. 13 on the Belgian Singles Chart (Wallonia), and No. 18 on the Finnish Singles Chart. The follow-up single “Love in This Club Part II”, which features American singer Beyoncé and rapper Lil Wayne, peaked at No. 18 on the Billboard Hot 100 and No. 7 on the Hot R&B/Hip-Hop Songs chart. Its third single “Moving Mountains” peaked at No. 18 on the Hot R&B/Hip-Hop Songs chart and reached No. 6 on the New Zealand Singles Chart. The album’s fifth single “Trading Places” peaked at No. 4 on the Hot R&B/Hip-Hop Songs chart. In September 2008, Usher announced he would embark on the 15-date tour One Night Stand, in which the audience is only females. On January 18, 2009, Usher performed with Stevie Wonder and Shakira at the We Are One: The Obama Inaugural Celebration at the Lincoln Memorial. He also sang “Gone Too Soon” at the memorial of Michael Jackson on July 7, 2009.

Raymond v. Raymond was released on March 26, 2010 in Germany, on March 30, 2010 in the US, and on April 26, 2010 in the UK. The album was expected to follow in Usher’s Confessions album’s footsteps. Raymond v. Raymond was released only months after Usher’s divorce from Tameka Foster. “Papers”, a song about divorce, was released as the first single for the album in October 2009. It topped the Hot R&B/Hip-Hop Songs chart for two consecutive weeks, becoming his tenth number one single on that chart. It also peaked at number 31 on the Billboard Hot 100 in the United States. Critics praised the song for its emotion. “Hey Daddy (Daddy’s Home)” was released as the second single on December 8, 2009. The single peaked at number 24 on the Billboard Hot 100 chart and number 2 on the Hot R&B/Hip-Hop Songs chart. The song was released as the second international single in July 2010. “Lil Freak” was announced as the album’s official second single in the United States. Usher and Nicki Minaj shot the music video for the song on March 9, 2010 in Los Angeles with director TAJ Stansberry. It reached number 8 on the Hot R&B/Hip-Hop Songs chart and number 40 on the Billboard Hot 100. It became Usher’s fourth Top 40 hit single from Raymond v. Raymond, when including the buzz single “Papers”.

“OMG”, which features will.i.am, is the third official US single and the first international single. The song received mixed reviews, complimenting the song’s dance and club vibe but criticizing the Auto-Tune effect. It reached number-one in Ireland, New Zealand, the United Kingdom, Australia and the United States. The song became his ninth number one in the United States, making him the first 2010s artist to collect number one singles in three consecutive decades, and only the fourth artist of all-time to achieve the feat. Usher also became the third artist to have at least one number one song from five consecutive studio albums. The song’s choreography and dance-heavy accompanying music video has been compared to that of “Yeah!”. “There Goes My Baby” was released to airplay as the album’s fourth single in the United States on June 15, 2010. The song reached number 25 on the Billboard Hot 100, and number-one on the Hot R&B/Hip-Hop Songs chart, becoming Usher’s eleventh number-one hit on that chart. The song ended up tying with “You Make Me Wanna” for fourth longest stay on the chart with 71 weeks. All of the album’s singles received very heavy air play. On April 7, 2010, Raymond v. Raymond debuted at number No. 1 on the US Billboard 200 chart, becoming his third consecutive No. 1 album and selling an impressive 329,107 copies in its first week of release, making him the first male artist since Eminem to have three consecutive albums debut at number one on the Billboard 200 chart. After one month of release the album was certified Gold by the RIAA. On June 17, 2010, the album was certified Platinum by the RIAA.

Raymond v. Raymond also dominated the International Charts, debuting inside the top 10 in Canada, the United Kingdom, Holland, Australia, Germany, Spain, and Italy. Due to the huge international success of Usher’s single “OMG” and the good first week sales for Raymond v. Raymond, the album reached number two in Australia and has been certified gold by the Australian Recording Industry Association (ARIA). The album debuted at number four in Canada and has been certified Gold by the Canadian Recording Industry Association (CRIA). Raymond v. Raymond debuted at number-two in the United Kingdom.

Usher announced on July 8, 2010, a follow-up extended play to his sixth studio album Raymond v. Raymond called Versus, and a deluxe edition of Raymond v. Raymond, both to be released on August 24, 2010. Usher described Versus as “the last chapter of Raymond v. Raymond“, and that it would explore the subjects of being newly single and a father. The album included 9 tracks, including 7 new tracks, Raymond v. Raymond single “There Goes My Baby”, and Justin Bieber single “Somebody to Love (Remix)”. The tracks would be included on a deluxe edition of Raymond v. Raymond. The album debuted at number four on the Billboard 200 chart and is preceded by the singles “DJ Got Us Fallin’ In Love” featuring Pitbull, for mainstream audiences, and “Hot Tottie” featuring Jay-Z, for urban circuits.

The first single from the album, “DJ Got Us Fallin’ In Love”, was released to iTunes on July 13, 2010, and sent to radio on July 20, 2010. Due to strong digital sales the song debuted at number nineteen on the Billboard Hot 100. The song became the fourth highest debut on the Billboard Hot 100 of his career, behind 1997’s “Nice & Slow” at number nine, 1998’s “My Way” at eight, and 2010’s “OMG” at number fourteen. Since its release, it has gained international success, peaking in the top 5 in the United States, Australia, and New Zealand. It reached the top 10 in Canada and Europe. It reached number-nine on the Billboard Hot 100 in its third week of release, and became the first time Usher has had two top-ten hits on the Billboard Hot 100 at the same time since his album Confessions. It also became Usher’s sixteenth Billboard Hot 100 top-ten hit of his career. The second single, Hot Tottie, reached number nine on the Hot R&B/Hip-Hop Songs chart and number twenty-one on the Billboard Hot 100.

Usher appeared at the 2010 MTV Video Music Awards on September 12, 2010. He then performed at the 2010 American Music Awards on November 21, 2010, and also won the awards for Male Soul/R&B artist and Favorite Soul/R&B album for his album Raymond v. Raymond. According to Rap-Up.com, Usher started working on his next studio album, again teaming up with long-time collaborator Rico Love. The OMG Tour began in November 2010 and ended on June 1, 2011.

On September 8, 2011, Usher appeared on Romeo Santos’ second single “Promise” from his debut studio album Formula, Vol. 1. The song was his first number-one on the Billboard Latin Songs chart.

Usher also made an appearance in the Super Bowl XLV halftime show to sing his song “OMG” with The Black Eyed Peas’ singer will.i.am.

In November 2011, Usher revealed that for his next album he was working on a new type of music which he has depicted as “revolutionary pop”, which combines different genres to form a new sound. His seventh studio album Looking 4 Myself was released on June 8, 2012 worldwide, and received generally positive reviews from contemporary music critics. American singer-songwriter and record producer Rico Love was interviewed by Billboard magazine, where he spoke about his relationships with artists and experiences. He commented on how Usher wanted to do things differently on the album compared to his previous efforts, saying: “What he wanted to do [on Looking 4 Myself] was explore himself musically. He stepped outside of what was safe and normal. He wanted to make an album that expressed where he was going sonically and not just where he’s been for the past 12 to 15 years. He’s growing, developing, moving, shaking, and being something that’s new, cultural, and that’s affecting people sonically. That’s kind of forcing the people to grow and elevate”. In an interview for MTV News, Usher stated that Looking 4 Myself is “the most artistic of an album” he has ever had in history. When questioned by Reuters during an interview regarding the latter quote, and how this project was different, Usher explained that he felt he was near a ‘rebirth’ and that prior to Looking 4 Myself, he felt restricted and conformed to a specific standard. He said to himself “I gotta go with what I feel and hopefully people will follow me”.

The lead single from Usher’s seventh studio album is titled “Climax”. It impacted Urban radio on February 21, 2012, and was made available for purchase as a digital download on February 22, 2012. It impacted US mainstream radio on March 13, 2012. The second single released from the album was “Scream” and the third single “Lemme See” which features Rick Ross. “Scream” was premiered on April 26, 2012, while “Lemme See” was premiered on May 8, 2012. On Billboard Hot R&B/Hip-Hop Airplay, “Climax” enabled Usher to add a second song of his in the six longest stays at number one for 11 weeks after “You Make Me Wanna” with 12 weeks.

In 2013, Usher substituted for CeeLo Green as a coach for the fourth season of NBC’s The Voice. His last act, Michelle Chamuel, lost the winning title to Danielle Bradbery, mentored by Blake Shelton. He returned for the sixth season and his last act, Josh Kaufman, won.

On March 19, 2013, Usher announced that his eighth studio album, titled UR, was in the works. Talking to The Fader, he described the album as “everything you can imagine”, saying that it’s “gonna be freaking out of here”. Singer-songwriter Eric Bellinger told Rap-Up that he, along with Jermaine Dupri, Bryan-Michael Cox, and Brian Alexander Morgan, was working on Usher’s next album. Bellinger compared the album’s music to Usher’s Confessions (2004), saying that it is “more R&B, more urban” than Usher’s Looking 4 Myself. The latter declared that his next album would show that he is “still Usher”. “Good Kisser”, a dance-heavy throwback R&B track, was released as the first single allowing Usher to achieve his 13th no.1 on the Airplay chart, tying Drake for most leaders in the list’s history. Produced by Pop & Oak, it was performed at The Voice. Since then, two other singles have been released from the album: “She Came to Give It to You” featuring Nicki Minaj and “I Don’t Mind” featuring Juicy J. The latter allowed Usher to lead the Rhythmic charts with the most number ones (13).

On August 25, 2014, Usher announced his UR Experience Tour in support of his then-titled eighth studio album UR. The UR Experience started in Montreal, Quebec on November 1 and ended in Tampa, Florida on December 14. The 27 city North American leg was supported by opening acts DJ Cassidy and R&B newcomer August Alsina. The European leg of the tour visited 23 cities and the support would be Nico & Vinz. “With The UR Experience, I want to give my fans an ever-changing live show full of surprises and special guests,” Usher says, via a press release. “I am really excited to be with my fans and give them an Usher experience like they’ve never seen or heard before.” While on tour, with the collaboration of Honey Nut Cheerios, he released “Clueless”, a new song that could be downloaded free using a code from specially-marked Honey Nut Cheerios boxes bought from Walmart.

On October 16, 2015, Usher released an interactive music video exclusively on the music streaming platform Tidal called “Chains” featuring artists Nas and Bibi Bourelly. “Chains” literally forces the viewer to confront the issue of racial profiling and police brutality head-on: By utilizing the webcam on the viewer’s computer as well as facial recognition technology, “Chains” paused mid-song whenever the viewer’s eyes deviate from the video. Usher performed the song for the first time at the Tidal X:1020 concert on October 20, 2015 at Brooklyn’s Barclays Arena. On January 14, 2016, after continual delays of his eighth album, Usher announced via Daniel Arsham Instagram post that he changed the title of the album from UR to Flawed. It was scheduled to be released in April 2016, but has been pushed back with no release date. On February 29, 2016, Yuna released “Crush” as the first single from her forthcoming album Chapters featuring Usher. On June 9, 2016, Usher released a new single from his expected forthcoming album Flawed on the music streaming platform Tidal titled “No Limit” featuring Young Thug, along with a second single titled “Crash” on June 10 for all digital platforms.

On June 12, 2016, it was reported that Raymond signed a management deal with business partner Scooter Braun. Braun already represented Justin Bieber and had a joint venture with Raymond and Bieber. This report was confirmed by Usher during a sit down interview with Ryan Seacrest at the 73rd annual Cannes Festival on June 21, 2016. Usher furthered his acting career, starring as American former professional boxer Sugar Ray Leonard in the 2016 American-Panamanian biographical sports film Hands of Stone about the career of Panamanian former professional boxer Roberto Durán. In it, he starred opposite of Édgar Ramírez, Robert De Niro and Ruben Blades. On August 26, 2016, Hands of Stone premiered worldwide. “Missin U” was also released as a third single by RCA Records for online streaming and digital download, along with “Champions (from the Motion Picture Hands of Stone)”, both on Vevo. On August 30, “Rivals” featuring Future was released and debuted exclusively on Tidal with its accompanying video. It was released on Vevo on September 2, 2016. On September 13, 2016, both “Missin U” and “Rivals” were sent to radio as the album’s third and fourth singles.

The album Hard II Love was released on September 16, 2016, and received generally positive reviews from contemporary music critics. It debuted at number 5 on the US Billboard 200, and sold 28,000 copies in the United States in its first week.^[126] It also became his seventh consecutive top ten album in the United States. The lead single, “No Limit” featuring rapper Young Thug initially was serviced to Urban radio on June 9, and eventually peaked at number 1 on the Mainstream R&B/Hip-Hop airplay chart, number 32 on the Billboard Hot 100, and number 9 on the Hot R&B/Hip-Hop Songs. On December 16, 2016, Chris Brown released “Party” as the second single from his forthcoming album Heartbreak on a Full Moon featuring Usher and Gucci Mane.

On October 12, 2018, Usher released his ninth studio album, titled simply A. The official tracklist contains 8 songs with features from Future and Gunna. The album was produced entirely by Zaytoven, who previously collaborated on Usher’s Raymond v. Raymond album as a co-producer for the single “Papers”.

Between November 9–17, 2018, Usher served as the headliner for the RNB Fridays Live concert series. The six date stadium tour in Australia and New Zealand sold over 150,000 tickets On November 14, 2018, Billboard reported that Usher signed a worldwide management deal with Luke Mitzman and 100 Management. It was also reported he is working on a follow up album that will be released in 2019. On December 2, 2018, Usher performed at the Global Citizen Festival: Mandela 100 in Johannesburg, South Africa, celebrating the legacy of Nelson Mandela. Usher and DJ Black Coffee performed a mash-up featuring the South African Indigenous Dance Academy (IDA).

Usher had a cameo in the crime film Hustlers, which was released on September 13, 2019, and stars Jennifer Lopez, Constance Wu, Keke Palmer, Cardi B, and Lili Reinhart.^[135] In September 2019, director Lorene Scafaria told Vulture magazine his cameo was written into the script in 2016, before the film went into development.^[136] Usher is featured on the film’s soundtrack, with his single ”Love in This Club“.^[137]

In March 2019, Usher posted a photo of himself in the studio next to a whiteboard with the title “Confessions 2” and a blurred out tracklisting. The following day producer Jermaine Dupri, who produced the original Confessions went live on Instagram and previewed new music.

On June 15, 2019, Usher, alongside Erykah Badu, headlined the second annual Smoking Grooves Festival at the Queen Mary Events Park in Long Beach, California.

On September 6, 2019, Usher returned for season seventeen of NBC’s The Voice. He joined John Legend team as this season’s battle advisor. On September 10, 2019, DJ Black Coffee released his single “Lalala” featuring Usher from his forthcoming album. It reached number one on the South Africa airplay charts. Usher appeared on Summer Walker’s debut album Over It, which was released on October 4, 2019. They collaborated on “Come Thru”, which samples “You Make Me Wanna…”, his hit from his second album, My Way. Time, Entertainment Weekly, and Paper all named it one of the best songs of the week.

On December 13, 2019, Usher released the lead single, “Don’t Waste My Time”, featuring British singer-songwriter Ella Mai for his upcoming ninth studio album. It was co-produced by longtime collaborators Bryan-Michael Cox and Jermaine Dupri. Usher, Ella Mai, and Jermaine Dupri performed the song on BET’s SOS: Saving Ourselves – A BET Covid 19 Relief Special, to benefit African American Communities Impacted By Coronavirus on April 22, 2020. It topped the Adult R&B Chart, becoming his fifth number one single on that chart.

Usher performed at the 62nd Annual Grammy Awards on January 26, 2020. Usher and Shelia E. performed a special tribute honoring Prince. This performance was teaser for the Let’s Go Crazy: The Grammy Salute to Prince concert at the Staples Center scheduled for January 28, 2020 on CBS featuring performances from, Alicia Keys, John Legend, Chris Martin, H.E.R., and more.

Usher had been set to host and perform at the 2020 iHeartRadio Music Awards, which had been set scheduled to broadcast live on Fox on Sunday, March 29. The event was postponed due to concerns over the spread of coronavirus.

Usher served as executive producer and judge on a dance competition series called The Sauce. The seven-episode series premiered on April 6, 2020, on the streaming service Quibi. On April 11, 2019, Usher released his second single, “SexBeat”, featuring former collaborators Lil Jon and Ludacris. It was co-written by Jermaine Dupri and Antoine Harris. The release of “SexBeat” came days after Lil Jon premiered the track on April 5 during an online music battle called #VERZUZ hosted by Swizz Beatz and Timbaland. He appeared on NBC’s Songland and released the song “California” featuring Tyga on June 15, 2020. On June 26, 2020, Usher released “I Cry”.

On September 4, 2020 Usher announced he will be headlining a 12 show residency at the Colosseum at Caesars’ Palace in Las Vegas, Nevada. The show is scheduled to start on July 16, 2021 and is slated to run until January 1, 2022. Live Nation Las Vegas and Caesars Entertainment will be donating $1 from every ticket purchased to Usher’s New Look foundation.

Usher released the single “Bad Habits” on September 10, 2020 as the second single off his forthcoming studio album. The music video directed by Chris Robinson accompanied the song. It topped the Adult R&B Chart, becoming his sixth number one single on that chart.

On June 30, 2022, Usher performed on NPR’s Tiny Desk Concerts series. He was joined by vocalists Eric Bellinger and Vedo, bassist, Dmitry Gorodetsky, trombonist Lemar Guillary, trumpeter Brandyn Phllips, saxophonist Jay Flat, keyboardist Darek Cobbs, guitarist Erick Walls and drummer Ryan Carr. A clip from the performance of Usher whispering “watch this” went viral on the internet as a meme.