Usher Trivia
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60 free Usher trivia questions with answers — music quiz, new questions added Aug 2026.
These Usher trivia questions cover the whole career of Usher Raymond IV, from a nine-year-old in a Chattanooga church choir to the Super Bowl LVIII halftime stage thirty years into his solo run. The easy questions are for casual fans: his birthplace, the album that sold 20 million copies, the singles that went to number one, the singer he duetted with on "My Boo", the teenager he signed and the talent show he coached. The harder half digs into the details: the boy band he was pulled out of at 13, the Boyz II Men song he sang at his audition, the summer he spent living with Sean Combs, the Sinatra album behind My Way, why 8701 is called 8701, the four consecutive number ones from Confessions, his two-month Broadway run in Chicago, the boxer he played in Hands of Stone, the Vegas residency and the wedding he squeezed in on Super Bowl Sunday. Expert questions cover chart records, Grammy categories and label history. Every answer was checked against Usher's Wikipedia article and its cited sources before publishing, and each question shows its citation once you have answered.
30 of 60 questions with answers and explanations. Play the quiz
Q 01Atlanta made Usher a star, but in which city was he born?
Dallas, Texas
Dallas, Texas was only his birthplace. When he was 12 his mother moved the family to Atlanta, a bigger city whose music scene could give his singing a stage.
Q 02In which city did Usher spend most of his childhood before his family moved to Atlanta?
Chattanooga, Tennessee
Chattanooga, Tennessee got a surprise in 2015, when he walked unannounced into an awards assembly at Dalewood, his old middle school, and presented a prize to a straight-A student.
Q 03Usher has been a part-owner of which NBA team since 2005?
Cleveland Cavaliers
The Cleveland Cavaliers: he joined the group that bought the team in 2005, so when LeBron James led it to the 2016 title, Usher became an NBA champion as an owner.
Q 04Which label, home to TLC, released Usher's debut album when he was 15?
LaFace
LaFace signed him in his early teens. He later called that debut "the wrong direction" and said its bad-boy image, all frowning for the camera, was never him.
Q 05Which Usher album sold more than a million US copies in its first week in 2004?
Confessions
Confessions almost went out without its biggest hit: when he first handed the album in, his label asked for more songs, and those extra sessions produced "Yeah!".
Q 06What was Usher's first number-one single on the Billboard Hot 100?
"Nice & Slow"
"Nice & Slow" reached number one in February 1998. "You Make Me Wanna..." had entered the UK chart at number one but stalled at number two at home.
Q 07Which two rappers are featured on "Yeah!"?
Lil Jon and Ludacris
Lil Jon and Ludacris guest on a track Lil Jon also produced. He then leaked it to DJs, and when the label came back from its Christmas break, radio had already played it thousands of times.
Q 08Which Usher single ended the 12-week run of his own "Yeah!" at number one?
"Burn"
"Burn" was the ballad first lined up to launch the album. It took over at number one in May 2004 and spent eight weeks there in all.
Q 09Which singer joins Usher and 21 Savage on the 2023 single "Good Good"?
Summer Walker
Summer Walker had already built her 2019 single "Come Thru" on a sample of his "You Make Me Wanna..." and brought him in to sing on it, so "Good Good" was a rematch.
Q 10Which teenage singer's career did Usher co-found a label to manage in 2008?
Justin Bieber
Justin Bieber sang for him in Atlanta at 13, and Justin Timberlake was reportedly keen to sign the Canadian too. Bieber went with Usher's new joint venture instead.
Q 11Which TV singing competition did Usher join as a panellist in 2013 and again in 2014?
The Voice
The Voice brought him in for CeeLo Green, and his singer Michelle Chamuel finished runner-up in 2013. He came back a year later and won the whole thing with Josh Kaufman.
Q 12Which singer played a guitar solo at Usher's 2024 Super Bowl halftime show?
H.E.R.
H.E.R. was back at the big game with her guitar: three years earlier she had sung and played "America the Beautiful" before kickoff at Super Bowl LV.
Q 13Which bachata star's 2011 duet "Promise" gave Usher his first number one on Billboard's Latin chart?
Romeo Santos
Romeo Santos had just gone solo from Aventura, and "Promise" came from his debut album. The track put Usher on a bachata rhythm, and the pair performed it together at that year's Latin Grammys.
Q 21Which slow jam was the second single from Usher's album 8701 to top the Hot 100?
"U Got It Bad"
"U Got It Bad" did it twice over. A Nickelback hit knocked it off after one week in December 2001, and a month later it took number one back for five more weeks.
Q 22In 2004 Usher became the first act since which group to have the year's top two Hot 100 singles?
The Beatles
The Beatles did it in 1964. Usher's year was built on passing number one between his own songs: twice in 2004 one of his singles was replaced at the top by another of his.
Q 23Whose private life, by his own account, inspired the cheating songs on Usher's 2004 album?
Jermaine Dupri's
Q 14Which Boyz II Men song did Usher sing to win a record deal on the spot?
"End of the Road"
"End of the Road" sealed the deal. A label scout had watched him on the TV talent show Star Search and arranged the audition with the label's co-founder.
Q 15Usher plays himself in a cameo in which 2019 film?
Hustlers
Hustlers has him stroll into the dancers' club as himself. Director Lorene Scafaria wrote the cameo into her script in 2016, three years before he signed on.
Q 16Usher's first solo song, "Call Me a Mack", appeared on the soundtrack of which 1993 film?
Poetic Justice
Poetic Justice starred Janet Jackson and Tupac Shakur. Five years after singing on its soundtrack at 14, he was picked by Jackson to open her Velvet Rope world tour.
Q 17With whom did the label send a 15-year-old Usher to live in New York for what was dubbed "Flavor Camp"?
Sean Combs
Sean Combs put him up at his own house for the stay. Usher later called those the hardest days of his life, yet Combs went on to executive-produce his debut album.
Q 18Which rapper, touring his first album, opened for Usher across North America in 2004?
Kanye West
Kanye West was promoting The College Dropout as the support act. Touring together helped land him a verse on the remix of one of Usher's number ones, its producer said.
Q 19Which DJ and producer brought Usher the idea for his Grammy-winning 2012 single "Climax"?
Diplo
Diplo drew it from his own life, a moment when a romance had peaked and was about to end. The two worked on the song for two months.
Q 20Usher's spokesperson said the 87 in the album title 8701 marks the year he first did what?
Sang in public
Sang in public: in 1987 he first sang for an audience, at church. The album did come out on August 7, 2001, but his team called that match a coincidence.
Jermaine Dupri's, he says. The producer had just fathered a child while he had a girlfriend, and he wrote his own story into the songs so listeners would wonder about Usher.
Q 24Which girl-group singer did Usher date from 2001 until shortly before his biggest album came out?
Chilli
Chilli of TLC split from him just before his album of cheating songs arrived, and fans read the lyrics as the reason. He answered that the story was "the creativity of music".
Q 25Which role did Usher take over on Broadway in 2006?
Billy Flynn in Chicago
Billy Flynn in Chicago was a hit for the box office, and his run was extended. Then strep throat struck, and doctors kept him off stage for what should have been his final week.
Q 26Which number-one single led Usher's 2008 album Here I Stand?
"Love in This Club"
"Love in This Club" got out early when its own producer, Polow da Don, leaked it. Once released, it leapt from number 51 to number one in a single week.
Q 27Which 2010 single made Usher one of the few artists to top the Hot 100 in three consecutive decades?
"OMG"
It features will.i.am and drew flak for its Auto-Tune, but hit number one in the US, UK, Ireland, Australia and New Zealand.
Q 28Which rapper is featured on "DJ Got Us Fallin' in Love"?
Pitbull
It came from the Versus EP; the urban-radio single from the same set, "Hot Tottie", featured Jay-Z.
Q 29Which former boxer did Usher play in the 2016 film Hands of Stone?
Sugar Ray Leonard
Sugar Ray Leonard lost his title to Roberto Durán in June 1980, then won it back five months later when Durán turned away mid-fight, the night remembered as "No más".
Q 30Usher made his acting debut with a recurring role on which UPN sitcom?
Moesha
Moesha cast him as a classmate and love interest for Brandy's title character across several episodes. The part led to a soap role and his first film offers within a year.