107 Taylor Swift Trivia Questions and Answers for Swifties

Are you a true Taylor Swift fan? Put your knowledge to the test with our exciting set of Taylor Swift trivia questions! Whether you’ve followed her from the days of “Teardrops on My Guitar” or just discovered her with “Folklore,” this quiz promises to challenge and entertain you. Grab your friends, sharpen your memories of America’s favorite pop-country star, and get ready to see who’s the ultimate Swiftie!

Taylor Swift Trivia Questions and Answers

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Early Life

In what year was Taylor Swift born?
Answer: 1989.
What is Taylor Swift’s middle name?
Answer: Alison.
In which U.S. state was Taylor Swift born?
Answer: Pennsylvania.
At what age did Taylor Swift first start playing guitar?
Answer: 12 years old.
Who inspired Taylor Swift to pursue country music?
Answer: Shania Twain.
What was the name of Taylor Swift’s debut album?
Answer: “Taylor Swift.”
Which song did Taylor Swift perform at her school talent show that helped her gain local fame?
Answer: “Big Deal” by LeAnn Rimes.
Taylor Swift moved to Nashville at what age to pursue her music career?
Answer: 14.
What was Taylor Swift’s first Billboard Hot 100 single?
Answer: “Tim McGraw.”
At what age did Taylor Swift sign her first record deal?
Answer: 15.
Which record label was the first to sign Taylor Swift?
Answer: Big Machine Records.
What songwriting contest did Taylor Swift win at age 11, prompting her to travel to Nashville?
Answer: A national poetry contest with her poem “Monster in My Closet.”
Which music legend did Taylor Swift open for in 2006 during her early career?
Answer: George Strait.
How old was Taylor Swift when she released her first album?
Answer: 16.
What personal milestone inspired the song “The Best Day” on her album “Fearless”?
Answer: Her relationship with her mother and family.

Breakthrough

Which 2008 album marked Taylor Swift’s breakthrough in the music industry?
Answer: “Fearless.”
What song from the album ‘Fearless’ became Taylor Swift’s first #1 on the Billboard Hot 100 chart?
Answer: “Love Story.”
At the 2009 MTV Video Music Awards, which song was Taylor Swift accepting an award for when she was interrupted on stage?
Answer: “You Belong With Me.”
What significant record did ‘Fearless’ set in terms of digital album sales?
Answer: It was the best-selling digital album by a female artist at the time.
Which song from ‘Fearless’ won the Grammy Award for Best Country Song in 2010?
Answer: “White Horse.”
How many Grammy Awards did Taylor Swift win in 2010, and which major category did she win for the first time?
Answer: She won four Grammy Awards, including Album of the Year for ‘Fearless.’
What headlining tour did Taylor Swift embark on in 2009-2010 to support ‘Fearless’?
Answer: The Fearless Tour.
Which 2010 album followed ‘Fearless’ and included the hit single “Mine”?
Answer: “Speak Now.”
What unique feature distinguished ‘Speak Now’ from Taylor Swift’s previous albums?
Answer: Taylor Swift wrote all the songs on the album without any co-writers.
What historic achievement did Taylor Swift accomplish with her ‘Speak Now’ World Tour?
Answer: It grossed over $123 million and became one of the highest-grossing tours of the decade.
Which 2012 album marked a significant genre shift for Taylor Swift from country to more pop-oriented sounds?
Answer: “Red.”
Which hit song from ‘Red’ spent 10 weeks at #1 on the Billboard Hot 100, making it one of her most successful singles?
Answer: “We Are Never Ever Getting Back Together.”

Key Albums and Songs

Which 2014 album marked Taylor Swift’s official transition to pop music?
Answer: “1989.”
What groundbreaking music video from ‘1989’ won the MTV Video Music Award for Video of the Year in 2015?
Answer: “Bad Blood.”
Which single from ‘1989’ became Taylor Swift’s first to top the Billboard Hot 100 for multiple weeks?
Answer: “Shake It Off.”
Name the song from ‘1989’ that Taylor Swift co-wrote with Ryan Tedder that discusses media perception of her personal life.
Answer: “Blank Space.”
What unique record did Taylor Swift set with the release of ‘Reputation’ in 2017?
Answer: It was the first album in history to have its opening week sales surpass one million copies for three consecutive albums.
Which song from ‘Reputation’ addresses her feuds with other celebrities and the media?
Answer: “Look What You Made Me Do.”
Name the 2019 album that features a collaboration with Brendon Urie of Panic! at the Disco.
Answer: “Lover.”
What is the name of the song from ‘Lover’ that promotes acceptance and equality, becoming an anthem for the LGBTQ+ community?
Answer: “You Need to Calm Down.”
Which 2020 album was Taylor Swift’s first “alternative” album, a surprise release recorded during the lockdown?
Answer: “Folklore.”
Name the song from ‘Folklore’ that won the Grammy Award for Song of the Year in 2021.
Answer: “Cardigan.”
Following ‘Folklore’, what was the title of the second surprise album Taylor Swift released in 2020?
Answer: “Evermore.”
What song from ‘Evermore’ features a duet with indie folk band Bon Iver?
Answer: “Evermore.”
Which album did Taylor Swift start re-recording in 2021 as part of her effort to own her early work, starting with her 2008 album?
Answer: “Fearless (Taylor’s Version).”
From ‘Fearless (Taylor’s Version)’, what is the name of a “From the Vault” song that features Maren Morris?
Answer: “You All Over Me.”
Which song from Taylor Swift’s debut album was inspired by a high school crush?
Answer: “Teardrops on My Guitar.”
What is the name of the song from the album ‘Speak Now’ that Taylor Swift wrote about her feelings on Kanye West’s interruption at the VMAs?
Answer: “Innocent.”
Which track from ‘Red’ lyrically describes a tumultuous relationship and is known for its emotional depth?
Answer: “All Too Well.”
Name the opening track of Taylor Swift’s album ‘1989’ that sets the theme for her pop transition.
Answer: “Welcome to New York.”
From the album ‘Reputation’, which song reflects on the beginnings of a relationship in the midst of media chaos?
Answer: “Delicate.”
Which song from ‘Lover’ features a collaboration with the Dixie Chicks and is a heartfelt homage to family and illness?
Answer: “Soon You’ll Get Better.”
In Taylor Swift’s ‘Folklore’, which track tells a fictional story of a teenage love triangle?
Answer: “Betty.”
From the album ‘Evermore’, which song narrates a story from three different perspectives within a fictional town?
Answer: “Ivy.”
Which song from ‘Fearless’ captures the youthful excitement and anticipation of turning fifteen?
Answer: “Fifteen.”
What is the lead single from Taylor Swift’s ‘1989’ that critiques the media’s portrayal of her dating life?
Answer: “Shake It Off.”
From ‘Speak Now’, which song is written about Taylor Swift’s admiration for her mother?
Answer: “The Best Day.”
Which track from ‘Reputation’ is known for its darker tone and introspective lyrics, discussing past feuds and personal struggles?
Answer: “I Did Something Bad.”

Collaborations

Which artist featured on Taylor Swift’s 2012 hit “Everything Has Changed”?
Answer: Ed Sheeran.
Who joined Taylor Swift for the duet “Both of Us” in 2012?
Answer: B.o.B.
In the music video for “Bad Blood” (2015), which famous rapper collaborated with Taylor Swift?
Answer: Kendrick Lamar.
Name the song from Taylor Swift’s ‘Lover’ album that features the Dixie Chicks.
Answer: “Soon You’ll Get Better.”
Which band did Taylor Swift collaborate with on the song “Exile” from her ‘Folklore’ album?
Answer: Bon Iver.
Who is featured in Taylor Swift’s “End Game” from her ‘Reputation’ album?
Answer: Ed Sheeran and Future.
For which soundtrack did Taylor Swift collaborate with Zayn Malik on the song “I Don’t Wanna Live Forever”?
Answer: The soundtrack for the film “Fifty Shades Darker.”
Who collaborated with Taylor Swift on the song “ME!” from her ‘Lover’ album?
Answer: Brendon Urie of Panic! at the Disco.
Which song from ‘Evermore’ features indie artist HAIM?
Answer: “No Body, No Crime.”
Taylor Swift released a version of “Lover” remixed by which popular DJ in 2019?
Answer: Shawn Mendes.
Who joined Taylor Swift for the live performance of “Only the Young” at the 2020 Democratic National Convention?
Answer: Nobody; this was a solo performance, but the trivia could explore her engagement in political themes.
What is the name of the song that features Taylor Swift on Calvin Harris’ 2016 album and includes a pseudonym for Taylor in the credits?
Answer: “This Is What You Came For,” credited to Nils Sjoberg.
Taylor Swift and which artist released “Coney Island” on the ‘Evermore’ album?
Answer: The National.
Which “From the Vault” track features Keith Urban and appears on ‘Fearless (Taylor’s Version)’?
Answer: “That’s When.”

Awards

What award did Taylor Swift win at the 2009 MTV Video Music Awards that was interrupted during her acceptance speech?
Answer: Best Female Video for “You Belong with Me.”
How many Grammy Awards did Taylor Swift win for her album ‘Fearless’?
Answer: Four, including Album of the Year.
Taylor Swift won her first Billboard Music Award in what year?
Answer: 2011.
Which Taylor Swift album earned her a second Album of the Year Grammy in 2016?
Answer: “1989.”
At the American Music Awards in 2018, Taylor Swift set a record for the most wins in what category?
Answer: Artist of the Year.
Which song won Taylor Swift her third Song of the Year Grammy in 2021?
Answer: “Cardigan” from the album “Folklore.”
Taylor Swift received the Brit Award for Global Icon in what year?
Answer: 2021.
In which year did Taylor Swift win her first Country Music Association Award for Entertainer of the Year?
Answer: 2009.
What special award did Taylor Swift receive at the Teen Choice Awards in 2011?
Answer: The Ultimate Choice Award.
Which Taylor Swift single won the Grammy for Best Music Video in 2016?
Answer: “Bad Blood.”
Taylor Swift was the youngest-ever recipient of the Grammy for Album of the Year in 2010. How old was she?
Answer: 20 years old.
Which award did Taylor Swift win at the MTV Europe Music Awards for the first time in 2012?
Answer: Best Live Act.
Taylor Swift has won the Billboard Woman of the Year Award multiple times. How many times has she won this as of 2023?
Answer: Three times (2011, 2014, 2019).
What unique award did Taylor Swift receive at the Nashville Songwriters Association International, making her the first artist to win it three times?
Answer: Songwriter/Artist of the Year.
Taylor Swift won a special Grammy in 2021 recognizing her achievements during the pandemic. What was the name of this Grammy?
Answer: There is no specific Grammy for achievements during the pandemic; she won Album of the Year for “Folklore.”

Personal Life

Where does Taylor Swift own homes in the United States?
Answer: Nashville, Tennessee; Beverly Hills, California; New York City, New York; and Watch Hill, Rhode Island.
What is the name of Taylor Swift’s beloved Scottish Fold cat, featured frequently on her social media?
Answer: Meredith Grey.
Taylor Swift is known for her philanthropy. What cause did she support by donating $1 million in 2016?
Answer: Louisiana flood relief.
What year did Taylor Swift testify in a court case regarding a groping incident, and what was the outcome?
Answer: 2017, and she won the case.
Taylor Swift has a holiday she particularly loves and often throws parties for. Which holiday is it?
Answer: Fourth of July.
Which political party did Taylor Swift publicly endorse for the first time in 2018?
Answer: The Democratic Party.
Taylor Swift has been known to surprise her fans with gifts and personal visits. What is this practice affectionately called by her fans?
Answer: “Swiftmas,” occurring around Christmas when she sends gifts to fans.
What is Taylor Swift’s favorite number, which she often references?
Answer: 13.
Taylor Swift has a younger sibling. What is his name?
Answer: Austin Swift.
Which hobby did Taylor Swift famously take up during the 2020 quarantine, as mentioned in her documentary ‘Folklore: The Long Pond Studio Sessions’?
Answer: Birdwatching.
In what year did Taylor Swift make her acting debut, and in which movie?
Answer: 2010, in the romantic comedy “Valentine’s Day.”
Taylor Swift attended high school in Pennsylvania. What was the name of the school?
Answer: Hendersonville High School.
What type of diet does Taylor Swift follow, as she has mentioned in interviews?
Answer: She has described herself as mostly following a pescatarian diet.
Which artist and friend painted the original oil painting that appeared on Taylor Swift’s ‘Red’ album cover?
Answer: Her friend, who is an artist, but not widely known outside of Swift’s personal circle.
What significant personal event did Taylor Swift celebrate by releasing the song “The Moment I Knew”?
Answer: Her 21st birthday, reflecting on a moment of personal disappointment.

Recent and Upcoming Projects

What was the title of Taylor Swift’s 2020 surprise album, her first of the alternative genre?
Answer: “Folklore.”
Which album did Taylor Swift release shortly after ‘Folklore’ at the end of 2020?
Answer: “Evermore.”
Taylor Swift began re-recording her earlier albums in 2021. What is the first album she re-released in this series?
Answer: “Fearless (Taylor’s Version).”
What is the name of the short film Taylor Swift directed that features the extended version of her song “All Too Well”?
Answer: “All Too Well: The Short Film.”
In 2022, Taylor Swift released ‘Red (Taylor’s Version)’. Which previously unreleased song from this album became a fan favorite?
Answer: “All Too Well (10 Minute Version).”
Which 2022 award show did Taylor Swift open with a performance from her ‘Eras Tour’?
Answer: The 2022 MTV Video Music Awards.
Taylor Swift announced a major tour in 2022. What is the tour called, celebrating her career-spanning catalog of music?
Answer: The Eras Tour.
Which album is Taylor Swift scheduled to re-record next, following ‘Fearless’ and ‘Red’?
Answer: “1989 (Taylor’s Version)” is speculated to be next, but as of my last update, there was no official release date.
Taylor Swift ventured into film by contributing an original song to which 2021 movie’s soundtrack?
Answer: “Where the Crawdads Sing.”
What significant recognition did Taylor Swift receive at the 2022 American Music Awards?
Answer: She was awarded the Artist of the Year and received the most awards of the night.