Taylor Swift's Biggest Hits Trivia Quiz

Answer: "The Life Of A Showgirl"

The lead single on "The Life Of A Showgirl" was released on October 3, 2025. The song paid homage to Ophelia from William Shakespeare. Swift's growth as an artist was evident with choosing Max Martin as producer. Max is famous for his glossy Swedish pop styling on many huge singles and "The Fate Of Ophelia" captured that poppy, New Wave-ish style.

Answer: "Speak Now"

"Speak Now" was Taylor's third album and released in 2010. The single "Mean" came out in 2011. The music video featured Taylor tied to train tracks like the Old Western movie scripts. The song won Best Country Solo Performance at the 2012 Grammy Awards and featured banjos and steel guitars on the track.

Answer: "Fearless"

"Fearless" was Taylor Swift's second album and released in 2008. The music video for "You Belong With Me" featured Taylor playing the dual role of a popular cheerleader and also a sympathetic less popular girlfriend. When Taylor won the MTV video award for the song, Kanye West took the moment to jump up on stage and declare that Beyoncé should have won the award.

Answer: "Folklore"

"Cardigan" was released on the 2020 album, "Folklore". The single was not the traditional bouncy pop song that Taylor had been releasing but more of a softer folk rock song including violins and a piano. Swift was nominated for Song of the Year for "Cardigan" and Best Pop Solo Performance at the 63rd Annual Grammy Awards.

Answer: "Midnights"

The chorus for "Anti-Hero" goes, "It's me, hi, I'm the problem, it's me". The song's theme was taking personal responsibility for your actions and it was a massive pop hit for Taylor. The song was released in 2022 on her tenth studio album, "Midnights".

Answer: "Reputation"

2017 brought us one of Taylor Swift's biggest selling albums, "Reputation". The album was loaded with huge pop hits and accompanied by Swift's first mega concert arena tour. The lead single "Look What You Made Me Do" addressed some of the media rumors swirling around the pop star. The song set a Guinness World Record for most streams in the first 24 hours of a song's release on Spotify.

Answer: "Lover"

2019 brought us "Cruel Summer" which teamed Taylor Swift with producer Jack Antonoff of Bleachers and songwriting co-credits to St. Vincent. The single was released in 2019 on Taylor's seventh studio album "Lover". The second single on the album was later recognized by Rolling Stone magazine as one of the 500 Greatest Songs Of All-Time.

Answer: "Red"

In 2012, Taylor Swift released the single "All Too Well" on her fourth album "Red". The original release was five and a half minutes long and discussed a mysterious ex-lover who did her wrong. Ten years later, Taylor re-recorded the song as "All Too Well (Taylor's Version) 10 Minute Version". Many attribute the lyrics to reference a short relationship with actor Jake Gyllenhaal.

Answer: "1989"

Taylor Swift began her career as a country music artist often seen playing an acoustic guitar. By 2014 and the release of "Shake It Off", Swift adopted a full pop star sound. The uptempo dance track featured clapping in the chorus. The song was included on her breakthrough pop album "1989" which paid homage to the year she was born.

Answer: "Taylor Swift" (Debut)

Taylor Swift's first three singles were "Tim McGraw", "Teardrops On My Guitar", and "Our Song" on her 2007 debut album. The latter song reached number 16 on the Billboard Hot 100. The song had a definite country music vibe and won the Video of the Year at the 2008 CMT Music Awards.