Getting your questions ready
Getting your questions ready
Beat the crowd
10 questions No timer
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 01In which city was Usher born?
Dallas, Texas
He is a Texan by birth only; the family moved to Chattanooga, then to Atlanta to find him a bigger stage.
Q 02In which city did Usher spend most of his childhood and join a church youth choir at nine?
Chattanooga, Tennessee
The city later named a road Usher Raymond Parkway in his honour, in 2001.
Q 03Usher's surname and suffix are what?
Raymond IV
His father was Usher Raymond III, who left when his son was a year old and reconciled with him shortly before dying in 2008.
Q 04How old was Usher when his self-titled debut album came out in 1994?
15
The songs were about sex, and the public had trouble believing a singer that young was singing them.
Q 05Which 2004 album remains the best-selling album by a Black artist of the 21st century?
Confessions
It sold nearly 1.1 million copies in its first week, then the most ever for a male R&B artist.
Q 06What was Usher's first number-one single on the Billboard Hot 100?
"Nice & Slow"
It topped the chart in January 1998; "You Make Me Wanna..." had gone to number one in the UK but not the US.
Q 07Which two rappers are featured on "Yeah!"?
Lil Jon and Ludacris
Lil Jon also produced it and called the crunk-meets-R&B sound "crunk&B".
Q 08For how many consecutive weeks did "Yeah!" top the Billboard Hot 100?
12
The song that finally knocked it off was Usher's own follow-up, "Burn".
Q 09Who duets with Usher on "My Boo"?
Alicia Keys
It gave the album its fourth straight number one and won the pair a Grammy for R&B duo performance.
Q 10Which teenage singer's career did Usher co-found a label to manage in 2008?
Justin Bieber
Raymond-Braun Media Group was a joint venture with the teenager's manager, Scooter Braun.
Q 11On which TV singing competition did Usher serve as a coach in 2013 and 2014?
The Voice
He replaced CeeLo Green, lost the first final with Michelle Chamuel and won the second with Josh Kaufman.
Q 12In what year did Usher headline the Super Bowl halftime show?
2024
It marked thirty years since his solo debut, and he married Jenn Goicoechea in Las Vegas the same night.
Q 13Which local R&B group was 12-year-old Usher a member of before his mother pulled him out?
NuBeginning
Their one album was re-released in 2002 as NuBeginning Featuring Usher Raymond IV; his mother later called it "a bad experience".
Q 21Which two 8701 singles both reached number one on the Hot 100?
"U Remind Me" and "U Got It Bad"
They spent four and six weeks on top respectively; "Pop Ya Collar" had flopped in the US a year earlier.
Q 22Which four singles from Usher's 2004 album went to number one consecutively?
"Yeah!", "Burn", "Confessions Part II", "My Boo"
He was the first artist ever to land four consecutive number ones on the Hot 100 Airplay chart; "Caught Up" only reached eight.
Q 23Whose personal life, rather than Usher's, actually inspired the infidelity songs on his 2004 album?
Q 14Which Boyz II Men song did Usher sing to win a record deal on the spot?
"End of the Road"
An A&R man had spotted him on Star Search and set up the audition with the label's co-founder.
Q 15Which label co-founder signed Usher as a teenager?
L.A. Reid
The two reunited in 2023 to found the independent label Mega with Larry Jackson's Gamma.
Q 16Usher's first solo song, "Call Me a Mack", appeared on the soundtrack of which 1993 film?
Poetic Justice
The Janet Jackson and Tupac drama came out a year before his own debut album.
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
He described the stint as the hardest days of his life, and the host ended up co-executive-producing his debut.
Q 18Which producer became Usher's close collaborator on his second album, My Way?
Jermaine Dupri
The two were still working together decades later on "Don't Waste My Time" and "SexBeat".
Q 19Usher named My Way after a 1969 album by which singer?
Frank Sinatra
The record also gave him his first UK number one with "You Make Me Wanna...".
Q 20Why is Usher's third album titled 8701?
It was released on August 7, 2001
It had been announced as All About U before leaks forced a retool and a rename.
Jermaine Dupri's
Fans assumed the songs explained his split from TLC's Chilli, and she did not exactly deny it on Atlanta radio.
Q 24Which TLC member did Usher date for three years from 2001?
Chilli
The relationship ended around the time his 2004 album's songs about cheating came out.
Q 25Which role did Usher take over on Broadway in 2006?
Billy Flynn in Chicago
Strep throat ended the run after two months and cost the production an estimated $400,000 in refunds.
Q 26Which number-one single led Usher's 2008 album Here I Stand?
"Love in This Club"
It became his eighth Hot 100 number one and the fastest-rising song of his career.
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
Édgar Ramírez played Durán, with Robert De Niro as his trainer.
Q 30Usher made his acting debut with a recurring role on which UPN sitcom?
Moesha
That led to his first film, The Faculty, and even a stint on The Bold and the Beautiful.