Bryson Tiller
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40 free Bryson Tiller trivia questions with answers — music quiz, new questions added Oct 2026.
Bryson Tiller went from uploading songs made at home to defining a sound. His 2015 debut, Trapsoul, blended moody R&B melodies with trap drums and rapped verses, and it has shaped how a good deal of R&B has sounded ever since. This quiz covers the whole story: his Kentucky upbringing and the day jobs that came before the music, the singles and albums that made his name, the older records he samples, and the guest verses that put him on some of the biggest hits of the past decade. There are questions on trophies, tours and music videos too, plus a few on the private life of an artist who famously keeps a low profile. It is written for fans who know the albums front to back and for casual listeners who know a hit or two. The questions are multiple choice, and every answer comes with a short explanation, so you will leave knowing a little more than when you started.
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Q 01Which milestone did Bryson Tiller reach in June 2020, years after topping the Billboard 200?
Graduating high school
Graduating high school came late for Bryson Tiller, who earned his diploma through Iroquois High School nearly five years after his debut album.
Q 02Which superstar shares guest vocals with Bryson Tiller on DJ Khaled's 2017 hit Wild Thoughts?
Rihanna
Rihanna and Bryson Tiller took Wild Thoughts to number two on the Billboard Hot 100, then performed it with DJ Khaled at the Grammys in January 2018.
Q 03Before fame, Bryson Tiller supported his first child by working at UPS and which pizza chain?
Papa John's
Papa John's and UPS paid the bills after Bryson Tiller took a break from music in 2013, the year before he uploaded the song that made his name.
Q 04Bryson Tiller's single Sorry Not Sorry samples sounds from which classic arcade fighting game?
Street Fighter II
Street Fighter II: The World Warrior supplies game sounds on Sorry Not Sorry, alongside the intro of the Carrie Lucas song Questions.
Q 05In which Kentucky city was R&B singer Bryson Tiller born and then raised by his grandmother?
Louisville
Louisville is where Bryson Tiller started singing and rapping at age 15, years before its mayor named March 12 after him.
Q 06Which Bryson Tiller debut single, made in his living room, climbed to number 13 on the Hot 100?
Don't
Don't first appeared online in October 2014, and Bryson Tiller nearly lost it for good: he deleted the upload until a friend talked him into restoring it.
Q 07Bryson Tiller turned down an offer to join OVO Sound, the label co-founded by which rapper?
Drake
Drake co-signed Bryson Tiller early and wanted him on OVO Sound, but Tiller signed with a major label instead in August 2015.
Q 08Which Canadian pop star sings with Bryson Tiller on Lonely Christmas, from Tiller's 2021 holiday EP?
Justin Bieber
Justin Bieber's own Christmas music helped inspire the EP, A Different Christmas, which Bryson Tiller made for fans spending the holidays alone.
Q 09Which honor did Bryson Tiller receive from his hometown in March 2016, along with a day in his name?
Key to the city
The key to the city went to Bryson Tiller on March 12, 2016, barely five months after his debut album, on what the mayor declared Bryson Tiller Day.
Q 10Bryson Tiller and Jazmine Sullivan recorded the 2017 title track for which HBO series from Issa Rae?
Insecure
Insecure premiered on HBO in 2016, and the duet made for it went on to earn Bryson Tiller and Jazmine Sullivan an NAACP Image Award nomination.
Q 11Which singer's 2018 single Could've Been features Bryson Tiller and earned two Grammy nominations?
H.E.R.
H.E.R. already knew Bryson Tiller well, having opened the North American leg of his Set It Off tour the year before their duet came out.
Q 12Which singer's 2025 single It Depends samples Usher's Nice & Slow and features Bryson Tiller?
Chris Brown
Chris Brown's single with Bryson Tiller reached number 16 on the Billboard Hot 100, and Usher himself later joined the pair on its remix.
Q 13Bryson Tiller's verse on Wild Thoughts rides the guitar riff of Maria Maria, a hit by which band?
Santana
Santana's Maria Maria runs all through Wild Thoughts, right down to ad-libs from Wyclef Jean, who co-wrote and produced the 1999 original.
Q 21Which producer gave Bryson Tiller two Trapsoul beats and bought him gear to record in a Miami hotel?
Timbaland
Timbaland handed over the beats for Sorry Not Sorry and Been That Way, then bought the equipment because Bryson Tiller dislikes big studios.
Q 22Bryson Tiller guests on the extended Playing Games, from which singer's 2019 debut album Over It?
Summer Walker
Summer Walker built Playing Games on Destiny's Child's Say My Name, and Bryson Tiller's verse is heard only on the extended cut, not in the video.
Q 23Bryson Tiller's breakthrough single borrows a lyric from Shake It Off, a 2005 song by which singer?
Mariah Carey
Q 14Which 2020 Bryson Tiller album, dedicated to his late grandmother, debuted at number five in the US?
Anniversary
Anniversary arrived five years to the day after Trapsoul and grew out of ideas Bryson Tiller found while digging through that album's archives.
Q 15Which Bryson Tiller mixtape song got an official release in 2024 after taking off on TikTok?
Whatever She Wants
Whatever She Wants began life on the second Slum Tiller mixtape and became a top-20 hit, with Bryson Tiller rapping instead of singing.
Q 16Which platform hosted Bryson Tiller's breakthrough 2014 uploads and later his Slum Tiller mixtapes?
SoundCloud
SoundCloud brought Bryson Tiller four million streams in six months for his breakthrough song, and he returned in 2023 to release music free of sample clearances.
Q 17Which fellow Kentucky rapper featured Bryson Tiller on the 2019 single Thru the Night?
Jack Harlow
Jack Harlow shares a hometown with Bryson Tiller, and the pair teamed up again on Luv Is Dro, from Harlow's album Thats What They All Say.
Q 18Which sportswear giant partnered with Bryson Tiller in 2017 to rebuild basketball courts in his hometown park?
Nike
Nike and Bryson Tiller reopened the rebuilt courts at Wyandotte Park on June 7, 2017, with a skills clinic for local children, less than two weeks after his second album came out.
Q 19At which 2016 ceremony did Bryson Tiller win both Best New Artist and Best Male R&B/Pop Artist?
BET Awards
The BET Awards of June 2016 handed Bryson Tiller both trophies on a night when he also performed, less than nine months after Trapsoul came out.
Q 20Which rock band's One More Light was knocked off number one by Bryson Tiller's True to Self in 2017?
Linkin Park
Linkin Park lost the top of the Billboard 200 when True to Self arrived with 107,000 units, a month ahead of its announced release date.
Mariah Carey released Shake It Off on The Emancipation of Mimi, and Bryson Tiller reworks one of its lines in his second verse.
Q 24Which Trapsoul single samples Swing My Way and earned Bryson Tiller his first Grammy nomination?
Exchange
Exchange was nominated for Best R&B Song at the 2017 Grammys, and it was the song Bryson Tiller picked for his first US television performance.
Q 25Which singer's remix Rambo: Last Blood appears on the deluxe edition of Bryson Tiller's Trapsoul?
The Weeknd
The Weeknd first shared the remix online in 2015, and the two singers performed it together in Berlin during the Trapsoul Tour.
Q 26Bryson Tiller's Outside samples Wait (The Whisper Song) by which rap act, who appear in its video?
Ying Yang Twins
The Ying Yang Twins scored a hit with the whispered original in 2005, and seventeen years later they turned up in person for Bryson Tiller's video.
Q 27Which New Orleans rapper does Bryson Tiller credit with making him fall in love with hip-hop?
Lil Wayne
Lil Wayne's radio singles were his way into rap, Bryson Tiller has said, though R&B remains what he calls his first love.
Q 28Which former B2K singer's debut solo album first made Bryson Tiller want to start singing?
Omarion
Omarion's first album reached Bryson Tiller through an uncle, and he began listening every day and singing along to what he heard.
Q 29What did Bryson Tiller say in 2017 he would probably never do, wanting to stay a shadowy figure?
Filmed interviews
Filmed interviews were what Bryson Tiller ruled out, keeping a low profile that one critic called among the singer's most endearing qualities.
Q 30Which singer supported Bryson Tiller on the European leg of his 2017 Set It Off tour?
SZA
SZA joined Bryson Tiller for the European dates that autumn, in the same year she released her debut album Ctrl.