Our list of the top 10 Taylor Swift’s songs presents a look at the work of one of the most loved and successful singer songwriters of the past twenty years. Taylor Swift is a artist who enjoys creating music across many genres. She got her start in country but quickly incorporated pop, electronic, rock, and other styles into her sound. As her albums progressed, one could witness her growth and development as a musician. As one of the best-selling artists out there, Taylor Swift has won many awards and accolades, including 10 Grammy Awards, 27 Guinness World Records, and an Emmy. In addition, she has achieved the most American Music Awards by an artist and the most Billboard Music Awards by a woman. Taylor Swift’s competition for radio dominance and awards has come mostly from other big time female recording artists such as Katy Perry, Lady Gaga Rihanna, Maria Carey and Beyoncé.
Taylor Swift’s debut singles, “Our Song” and “Teardrops on My Guitar,” were released in 2006 and quickly gained traction. In 2010, 2015, and 2019, Taylor Swift was named on Time’s 100 most influential people in the world lists. Billboard named her Woman of the Decade for the 2010s. In addition, she was on Forbes Celebrity 100 list in 2016 and 2019.
Top 10 Taylor Swift Songs
# 10 – I Knew You Were Trouble
Kicking off our Taylor Swift Sings list is “I Knew You Were Trouble,” which was released to promote the album Red in 2012. Co-written with Max Martin and Shellback, a pair of Swedish songwriters who have produced hits like “I Knew You Were Trouble” and “We Are Never Ever Getting Back Together,” the song has been described as a “breakup banger.” The track premiered on Good Morning, America, where Taylor Swift called it “one of [her] favorites on the album” because of the sheer chaos it felt like. The song is about ignoring all the red flags someone is throwing up and being frustrated with yourself when they hurt you like you knew they would. It was inspired by Harry Styles, who showed the world he was a cheater. “I Knew You Were Trouble” peaked twice on Billboard Hot 100, once at #3 and once at #2.
# 9 – Cardigan
Released as the first single for the album Folklore in 2020, “Cardigan” is written from the perspective of Betty, one of two young women involved in an unfortunate love triangle. It’s one of three songs about the triangle, which was between Betty, James, and an unnamed young woman. The day it was released on Spotify, the song had the biggest opening day for an album released by a female artist. It even broke the Guinness World Record. Unlike the hype built up surrounding other singles before they released, Taylor Swift opted to announce this one mere hours before it came out. Released during COVID-19, Taylor Swift says that the pandemic reminded her “that nothing is guaranteed,” so she just wanted to “put it out into the world.” “Cardigan” peaked at #11 of Billboard’s The 100 Best Songs of 2020, as well as # 6 on Cleveland’s Best Songs of 2020 and #3 on Complex’s Waiss Aramesh’s Best Songs of 2020.
# 8 – Bad Blood (ft. Kendrick Lamar)
Written alongside Max Martin and Shellback, “Bad Blood” was released from the 2014 album, 1989. The pop song features heavy, stomping drums with a military-esque “Hey!,” a common favorite with Martin. The song is about losing a close friend and betrayal by them. Though the song is directly about a female musician in the music industry who made attempts to sabotage her tour, Swift kept the lyrics vague, as she wanted “people to apply it to a situation where they felt betrayed in their own lives.” The remix version of the song, which features Kendrick Lamar, was released as the 4th single off the album. It gained popularity worldwide, reaching #1 in New Zealand, Canada, Australia, and Scotland, as well as #1 on Billboard Hot 100, Mainstream Top 40, and Adult Top 40.
# 7 – You Belong with Me
“You Belong with Me” was released as a single in November 2008 as part of an iTunes-exclusive campaign to promote Fearless, Swift’s second album. The song was inspired by a fight she overheard, in which her male friend argued with his girlfriend over the phone. She co-wrote “You Belong with Me” with Liz Rose, who assisted in fleshing out the song’s storyline. The pop-country song peaked at #2 on the Hot 100 list and was the first country song to reach #1 on the Radio Songs all-genre chart since 1990. It was in the top 10 in several countries, including Australia, New Zealand, Canada, and the US.
The music video, produced by Roman White, was shot at her younger brother’s high school. The video won Best Female Video at the 2009 MTV Video Music Awards, which is famed as the night Kayne proclaimed that Beyonce’s “Single Ladies” was “the best music video of all time.” Though the interruption kept Swift from giving her acceptance speech, Beyonce gave her the opportunity to finish it when “Single Ladies” won Video of the Year.
# 6 – We Are Never Ever Getting Back Together
The lead single track on Red, “We Are Never Ever Getting Back Together” sings about an ex-partner who wants to rekindle a relationship the narrator simply wants to move on from. The song came about because a friend of her ex came by her studio as she was working with producers Max Martin and Shellback for clarity on a rumor he had heard. Upon sharing more details with her producers, Martin declared that they were going to write that song. The song premiered in August 2012 on a Google+ live chat, where she reportedly joked that the song was “really romantic… touching and sensitive… to my lovely ex-boyfriend.” “We Are Never Ever Getting Back Together” broke the Guinness World Record for Fastest Selling Single in Digital History. It also held #1 on Billboard Hot 100 chart for over a week, as well as topping the charts in Canada and New Zealand.
# 5 – Love Story
“Love Story” was the lead single off the album Fearless. This love song was inspired, as many of Taylor Swift’s songs are, by a disagreement with her parents about a boy she thought she was in love with. Surprisingly, her parents were correct in thinking that he was a creep, according to Swift. She also drew inspiration from Romeo and Juliet, though she gave it the happy ending she had always wanted for Juliet. While the song didn’t initially garner support from her parents or record label, she fought for its production. “Love Story” is a mid-tempo country-pop song sung from the perspective of Juliet. The song was re-recorded in 2021 after Scooter Braun’s company bought her master records. It was dropped in 2021 on Valentine’s Day and topped County charts at #1, just as it had when it was originally released.
# 4 – Teardrops on My Guitar
“Teardrops on My Guitar” was released on her self-titled debut album, as well as on her second studio album, Fearless. She worked with Liz Rose to write the piece and it was produced by Nathan Chapman. “Teardrops on My Guitar” was about Drew Hardwick, a classmate, and friend that she was crushing on hard but who was clueless about her feelings. Because he had a crush on another classmate, she kept her feelings a secret. Two years following the release of the album, he stood in her driveway while she rejected him, telling him “you’re too late.” He and his wife were arrested in 2015 for child abuse, so she dodged a bullet. The song peaked at #13 on the Billboard Hot 100 and was her debut entry on the Billboard Year-End Hot 100.
# 3 – Our Song
Produced by Nathan Chapman, “Our Song” was released as the third single from her self-titled debut studio album, which both surprised and pleased Taylor Swift. She wrote the song while in high school about a boyfriend with whom she didn’t have a song. However, the song itself was written to be performed in the talent show as a freshman. The song resonated with her classmates, who months later would be stopping her in the hallway and commenting on or even singing the song. The song talks about a couple who made parts of their life into their song. She wanted it to be the last track on the album in hopes that it would subliminally encourage listeners to play it again. “Our Song” held the number 1 spot on the Hot Country Songs chart for six weeks, which made Swift the youngest performer to compose and sing a chart-topping country song.
# 2 – Shake It Off
When “Shake It Off” was released, the song was everywhere. It was even referenced in an episode of The Big Bang Theory, “The Anxiety Optimization.” The song was a single off the album 1989, which is named for the year she was born. It was another collaboration with Max Martin and Shellback. Swift has referred to the album as a “rebirth” for her. “Shake It Off” was a diss track in response to rumors spread following Red, which released in 2012. Throughout the song, “shake it off” is said 36 times while the word “shake” is said a total of 70. “Shake It Off” peaked at #1 on the Hot 100 list, where it lasted two weeks. In one scene of the music video, which was directed by Mark Romanek, Swift rounded up a bunch of fans and surprised them with a dance.
# 1 – Blank Space
We close out our Top 10 Taylor Swift songs list with the 1989 amazing song “Blank Space.” “Blank Space” made Taylor Swift the first woman to dethrone her own song, “Shake It Off,” on the Hot List. The single spent seven weeks at the top of the list from 2014 to 2015. A collaboration with Max Martin and Shellback, the song was inspired by the media’s inaccurate portrayal and unnecessary criticism of her romantic life. It was satirical, mocking the perspective that she was a serial-date and a “psychopath.” The electropop song contains the often misheard line “Got a long list of ex-lovers,” which is often heard as “All the lonely Starbucks lovers.” Starbucks’ response was “Wait, it isn’t?”
The music video for “Blank Space” was shot primarily at Oheka Castle on Long Island, though some scenes were captured at Woolworth Estate. The video was leaked by Yahoo! the day before it was scheduled to premiere on Good Morning, America. It won Best Pop Video and Best Female Video at the MTV Video Music Awards in 2015. The RIAA certified the song as platinum eight times. It also topped music charts in Iceland, Canada, Scotland, Australia, and South Africa.
Top 10 Taylor Swift Songs article published on Classic RockHistory.com© 2021
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