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The ultimate Taylor Swift playlist
Taylor Swift, one of the most influential artists of the 21st century, has sold over 200 million records worldwide and won 14 Grammy Awards.
With 11 studio albums, Billboard named her the top female artist of the 2010s, and she is the only artist to win Album of the Year four times at the Grammys. This playlist takes you through the times that formed Taylor Swift’s music.
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Our Song – 2006
“Our Song” is from Taylor Swift’s first album, which came out in 2006. Swift wrote it all by herself, and it was her first song to reach No. 1 on the Billboard Hot Country Songs chart.
It was certified 4× Platinum by the RIAA and helped her become known in country music. This song is excellent for a Taylor Swift playlist because it was her first big hit and shows her songwriting talent when she was young.
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You Belong With Me – 2008
“You Belong With Me” is a song by Taylor Swift from her 2008 album named Fearless. It is one of her biggest songs that got to many different people.
The song got to No. 2 on the Billboard Hot 100 and won the MTV Video Music Award for Best Female Video in 2009. Co-written with Liz Rose, it highlights Swift’s talent for creating lyrics.
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Love Story – 2008
“Love Story” is a song by Taylor Swift from her 2008 album Fearless. It is one of her most famous songs. Swift wrote it all by herself, and it gives a new twist to Shakespeare’s Romeo and Juliet, making it end happily.
The song reached No. 4 on the Billboard Hot 100 and was number one in several countries, like Australia. It got 8× Platinum certification from the RIAA. The song was necessary for her change from country music to popular music.
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Mean – 2010
“Mean” is a song by Taylor Swift from her 2010 album Speak Now, and she wrote it all by herself. The song answers harsh critics and shows how she can turn her experiences into strong, uplifting melodies.
It won two Grammy Awards in 2012 for Best Country Song and Best Country Solo Performance. “Mean” reached No. 11 on the Billboard Hot 100 and got a 3× Platinum certification from the RIAA.
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All Too Well (10 Minute Version) – 2021
“All Too Well (10 Minute Version)” is on Red (Taylor’s Version), which came out in 2021. Taylor Swift and Liz Rose wrote this long song.
It started at No. 1 on the Billboard Hot 100, becoming the longest song (10 minutes and 13 seconds) to reach the top of the chart. The song got a nomination for Song of the Year at the 2023 Grammy Awards.
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I Knew You Were Trouble – 2012
“I Knew You Were Trouble” is a song by Taylor Swift from her 2012 album Red. The song was written by Max Martin and Shellback.
It has dubstep and electronic sounds, showing a significant change in how it was made. It reached No. 2 on the Billboard Hot 100 and got a 7× Platinum certification from the RIAA.
The song got a lot of good reviews for being new and different. It was also nominated for awards at the MTV Video Music Awards and the Grammys.
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Blank Space – 2014
“Blank Space” is a popular song by Taylor Swift from her 2014 album 1989. It was written together with Max Martin and Shellback.
It got to No. 1 on the Billboard Hot 100, making it her third song to reach the top and staying there for seven weeks. It got three Grammy Award nominations and won the American Music Award for Song of the Year.
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Shake It Off – 2014
“Shake It Off” is the first song from Taylor Swift’s 2014 album 1989. It shows her move from country music to pop music. It started at No. 1 on the Billboard Hot 100 and stayed in the top 10 for 24 weeks.
The song got three Grammy Award nominations, including for Record of the Year and Song of the Year. Its huge success and influence make it a must-have for the perfect Taylor Swift playlist.
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Delicate – 2017
“Delicate” is an excellent song from Taylor Swift’s 2017 album Reputation. Max Martin, Shellback, and Ali Payami wrote it. It mixes gentle electropop sounds with personal singing.
“Delicate” wasn’t a typical radio single at first, but it became popular over time, reaching the top of Billboard’s Adult Pop Songs and Mainstream Top 40 charts.
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Cruel Summer – 2019
“Cruel Summer” is an excellent song from Taylor Swift’s 2019 album Lover. It was written together with Jack Antonoff and St. Vincent. It tells the story of a hidden and passionate summer love.
It wasn’t released as a single initially, but it became very popular with fans and went viral on social media.
In 2023, it was officially played on the radio and then got to No. 1 on the Billboard Hot 100. “Cruel Summer” has become a big hit, even if it took some time.
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You’re On Your Own, Kid – 2022
“You’re On Your Own, Kid” is the fifth song on Taylor Swift’s 2022 album Midnights. The song talks about being independent and growing as a person.
It reached No. 8 on the Billboard Hot 100, although it was not released as a single. Its chart success and theme make it an excellent fit for a perfect Taylor Swift playlist.
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Anti-Hero – 2022
“Anti-Hero” is the main song from Taylor Swift’s 2022 album Midnights. Taylor Swift and Jack Antonoff worked together to write and produce it.
The song talks about being hard on yourself and unsure about who you are. When it came out, it started at No. 1 on the Billboard Hot 100 and stayed there for eight weeks.
It became Swift’s longest-running No. 1 hit and helped her become the first artist to have all 10 spots in the top 10 on the Billboard Hot 100.
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Betty – 2020
“Betty” is the fourteenth song on Taylor Swift’s 2020 album Folklore. Swift and Joe Alwyn worked together to write and produce it.
The song tells a made-up story about a teenage love triangle. It is from the point of view of a boy named James who wants to say sorry to a girl named Betty.
It includes sounds from country and folk music. “Betty” started at No. 6 on Billboard’s Hot Country Songs chart and No. 42 on the Billboard Hot 100.
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Champagne Problems – 2020
“Champagne Problems” is the second song on Taylor Swift’s 2020 album Evermore. Taylor Swift and Joe Alwyn worked together to write and produce it, with Joe using the name William Bowery.
The song is about a woman who says no to a marriage proposal and how she feels after that. When it came out, it started at No. 21 on the Billboard Hot 100.
Don’t miss out on how Taylor Swift saved the day at the 2025 Grammys.
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Last Updated: September 24, 2025
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