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50 free 2020s Music trivia questions with answers — trivia quiz, new questions added Aug 2026.
The 2020s began with cancelled tours and livestreamed lockdown albums and turned into the decade of TikTok hits, vinyl outselling CDs and the Eras Tour. These 50 questions cover the pop records (Anti-Hero's clean sweep of the top 10, As It Was's 15 weeks at number one, Blinding Lights' 90 weeks on the chart), the breakout stars (Olivia Rodrigo, Sabrina Carpenter, Chappell Roan, Doechii), the country and regional Mexican booms, K-pop's first Grammy nomination, reggaeton's takeover of the Hot 100, and the rock comebacks from AC/DC to the last Beatles record. Built for a music round where everyone in the room has heard the songs, even if they can't name the year. Every answer is sourced.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which Weeknd single spent a record 90 weeks on the Billboard Hot 100?
Blinding Lights
It came from his fourth album, After Hours, and became the biggest Hot 100 song of all time.
Q 02Which Taylor Swift song made her the first artist to hold the entire Hot 100 top 10 at once?
Anti-Hero
Its parent album went on to win Album of the Year at the 66th Grammys.
Q 03Which 2020 Swift album spent a record eight weeks atop the Billboard 200 and won Album of the Year?
Folklore
Journalists filed it and its sister album Evermore as "pandemic projects" built on indie folk and chamber pop.
Q 04Which ten-minute track became the longest song ever to reach number one on the Hot 100?
All Too Well (Taylor's Version)
It was never even released as a single; it appeared on Red (Taylor's Version) in 2021.
Q 05Which was the first re-recorded album ever to reach number one on the Billboard 200?
Fearless (Taylor's Version)
It and Red (Taylor's Version) were the two best-selling country albums of 2021.
Q 06Which Olivia Rodrigo single debuted at number one in January 2021 and won Best Pop Solo Performance?
Drivers License
She also took Best New Artist and Best Pop Vocal Album for Sour at the same ceremony.
Q 07Which singer broke through in 2024 with "Espresso" after opening for Taylor Swift on tour?
Sabrina Carpenter
Her album Short n' Sweet put "Espresso", "Please Please Please" and "Taste" all in the Hot 100 top three.
Q 08Whose single "Good Luck, Babe!" preceded a Best New Artist win at the 67th Grammys?
Chappell Roan
Her debut album is The Rise and Fall of a Midwest Princess, home to "Pink Pony Club" and "Hot to Go!".
Q 09Which Miley Cyrus song became the fastest to reach 100 million Spotify streams, within a week?
Flowers
It brought her first Grammy wins: Record of the Year and Best Pop Solo Performance.
Q 10Which Billie Eilish song from the Barbie soundtrack won her a second Academy Award?
What Was I Made For?
Her first Oscar was for the Bond theme "No Time to Die".
Q 11Which Lady Gaga and Ariana Grande duet from Chromatica topped the Hot 100?
Rain on Me
It won Best Pop Duo/Group Performance at the 63rd Grammys.
Q 12Which Dua Lipa album produced "Don't Start Now" and "Levitating"?
Future Nostalgia
Both singles peaked at number two in the US, and the album won Best Pop Vocal Album.
Q 13What was Harry Styles' first Billboard Hot 100 number one, in 2020?
Watermelon Sugar
It came from his 2019 album Fine Line and won Best Pop Solo Performance.
How many non-consecutive weeks did "As It Was" spend at number one on the Hot 100?
Q 21What was Doja Cat's first number-one single?
Say So
Her album Planet Her went on to spend 26 weeks in the Billboard 200 top 10.
Q 22Which Megan Thee Stallion collaboration with Beyoncé won Best Rap Song and Best Rap Performance?
Savage
She was named Best New Artist at the same 63rd Grammys.
Q 23Who became only the third woman to win Best Rap Album, for Alligator Bites Never Heal?
Doechii
The mixtape spawned "Nissan Altima" and "Denial Is a River".
Q 24Which 2022 Beyoncé album took her into house music and won Best Dance/Electronic Album?
15
Its album, Harry's House, took Album of the Year at the 65th Grammys.
Q 15Which Weeknd song reached number one seven years after its original 2016 release?
Die for You
It came from Starboy; an Ariana Grande remix helped push it to the top.
Q 16What was SZA's first Hot 100 number one, from her album SOS?
Kill Bill
All 23 tracks on SOS charted on the Hot 100 in the same week.
Q 17How many weeks did SOS spend atop the Billboard 200, a record for a female R&B artist since 1986?
Twelve
The previous mark belonged to Whitney Houston's self-titled debut.
Q 18Who scored a first number one with "Bad Habit" and won Best Progressive R&B Album for Gemini Rights?
Steve Lacy
He came up as the guitarist in the band The Internet before his solo run.
Q 19Which Kendrick Lamar diss track won both Record and Song of the Year at the 67th Grammys?
Not Like Us
He performed it at the Super Bowl halftime show with SZA shortly afterwards.
Q 20Which Nicki Minaj single was the first by a female rapper to debut at number one since 1998?
Super Freaky Girl
The last to do it had been Lauryn Hill with "Doo Wop (That Thing)".
Renaissance
Its lead single "Break My Soul" went to number one and "Cuff It" won Best R&B Song.
Q 25Which number one single led Beyoncé's first country album, Cowboy Carter?
Texas Hold 'Em
The album won Album of the Year and Best Country Album at the 67th Grammys despite zero CMA nominations.
Q 26Which 2024 Charli XCX album became her biggest seller and spawned "Apple" and "Guess"?
Brat
It won Best Dance/Electronic Album, and "Von Dutch" took Best Dance Pop Recording.
Q 27Which Lizzo single won Record of the Year at the 65th Grammys?
About Damn Time
It was the lead single from her fourth album, Special, and reached number one on the Hot 100.
Q 28Which BTS song earned the first Grammy nomination for a Korean pop act, in November 2020?
Dynamite
They were nominated again the following year with "Butter".
Q 29Which Blackpink album was the first girl-group number one on the Billboard 200 since 2008?
Born Pink
It also topped the US and UK album charts simultaneously, a girl-group first since Destiny's Child's Survivor in 2001.
Q 30Which Japanese duo's "Idol" was the first Japanese-language song to top Billboard Global Excl. US?
Yoasobi
Oricon and Billboard Japan both named it the best-performing song of 2023 at home.