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50 free Taylor Swift Albums trivia questions with answers — music quiz, new questions added Aug 2026.
Twelve studio albums, four re-recordings, 15 Billboard 200 number ones and 98 weeks at the top: Taylor Swift's discography is its own subject. This quiz goes era by era, from the 2006 debut she promoted on Myspace and wrote during her freshman year of high school, through the most-awarded country album of all time, the album she wrote entirely alone, the breakup record that matched a Beatles chart feat, the synth-pop rebirth named for her birth year, the wiped social media before Reputation, the pastel Lover, the surprise quarantine sister records, the 3am Edition, the two-million-unit week and the four-million-unit week. These 50 questions cover producers (Nathan Chapman to Max Martin, Jack Antonoff and Aaron Dessner), lead singles, Grammy wins, first-week numbers, chart records, the Big Machine and Republic contracts and the masters dispute that led to four Taylor's Versions. Easy questions are the famous facts; the expert tier asks about co-writers, weeks at number one and which album the Library of Congress preserved. Every answer is cited to a page we checked, with a short explanation so you learn something even when you miss.
30 of 50 questions with answers and explanations. Play the quiz
Q 01In what year was Swift's self-titled debut album released?
2006
She made it with producer Nathan Chapman during her freshman year of high school.
Q 02Which social network did Swift use to reach teenagers with her debut?
Myspace
Teenagers had been excluded as a target audience for country music.
Q 03Which two debut-album singles topped the Hot Country Songs chart?
Our Song and Should've Said No
'Teardrops on My Guitar' reached the pop top 10.
Q 04Swift's debut was the longest-charting album of which decade on the Billboard 200?
The 2000s
It also spent 24 weeks at number one on the country albums chart.
Q 05At which ceremony did Swift's second album win Album of the Year in 2010?
The Grammy Awards
It is the most-awarded country album of all time, having already swept the CMA and ACM album prizes in 2009.
Q 06Which singer co-wrote on Fearless alongside Liz Rose and John Rich?
Colbie Caillat
Hillary Lindsey also had co-writing credits on the album.
Q 07How many weeks did Fearless spend atop the Billboard 200?
11
It was the only 2000s album to spend a full year in the top 10.
Q 08Which Fearless songs broke through on both country and pop radio?
Love Story and You Belong with Me
The album became her international breakthrough, topping charts in Canada and New Zealand.
Q 09Which album did Swift write entirely by herself?
Speak Now
She framed it as a loose concept album about the unsaid things she wanted to tell people.
Q 10Which Speak Now single won Best Country Song and Best Country Solo Performance at the 2012 Grammys?
Mean
The album itself was nominated for Best Country Album.
Q 11Which producer worked on Swift's first four albums, from the debut through Red?
Nathan Chapman
Red added Max Martin, Shellback, Jeff Bhasker, Dan Wilson, Jacknife Lee and Butch Walker to the mix.
Q 12Red made Swift the first act since which band to have three straight albums top the chart 6+ weeks?
The Beatles
Red spent seven weeks on top.
Q 13Which Red single became Swift's first Billboard Hot 100 number one?
We Are Never Ever Getting Back Together
'I Knew You Were Trouble' reached number two.
Q 21Reputation was Swift's first tour of what kind?
All-stadium
The 2018 Reputation Stadium Tour became the highest-grossing US tour in history at the time.
Q 22Reputation was Swift's fourth straight album to sell how many US copies in its first week?
One million
Speak Now, Red and 1989 had each done it before.
Q 23Which album was Swift's first after leaving Big Machine for Republic Records?
Lover
The move triggered the public dispute over ownership of her earlier masters.
Q 24How did Swift describe Lover?
Q 14Where did Red land on Rolling Stone's 2023 revision of the 500 Greatest Albums?
99th
Critics retrospectively called it her career-defining album.
Q 15What is the album 1989 named after?
Swift's birth year
She called it a symbolic rebirth as she moved from country to pop.
Q 16Which three 1989 singles hit number one on the Hot 100?
Shake It Off, Blank Space and Bad Blood
'Style' and 'Wildest Dreams' made the top ten.
Q 17For roughly how long was 1989 withheld from free streaming services?
Nearly three years
The stand sparked an industry debate about streaming and record sales.
Q 18Which Swift album did the Library of Congress add to the National Recording Registry in 2026?
1989
It also won Album of the Year at the 2016 Grammys.
Q 19Which electronic musician is credited as a producer on 1989 alongside Max Martin and Shellback?
Imogen Heap
Jack Antonoff and Ryan Tedder also produced tracks.
Q 20What did Swift do to her website and social accounts before announcing Reputation?
Cleared them all out
The blackout generated huge media attention before 'Look What You Made Me Do'.
A love letter to love
Its visuals leaned heavily on bright pastel colours.
Q 25Which Lover track became a Hot 100 number one four years after the album, in 2023?
Cruel Summer
It was released as the album's fifth single during the Eras Tour.
Q 26Which producer made Lover with Swift alongside Joel Little, Louis Bell and Frank Dukes?
Jack Antonoff
He has worked on every Swift studio album since 1989.
Q 27On what date was Folklore surprise-released?
July 24, 2020
It was written during quarantine with Aaron Dessner and Jack Antonoff working remotely.
Q 28Which member of the National produced much of Folklore and Evermore?
Aaron Dessner
Evermore was recorded mainly at his Long Pond Studio in the Hudson Valley.
Q 29Which Folklore song went to number one on the Hot 100?
Cardigan
'Exile', featuring Bon Iver, and 'The 1' also made top tens internationally.
Q 30Folklore's Grammy win made Swift the first woman to win Album of the Year how many times?
Three
Midnights later made her the first artist of any gender to win it four times.