Taylor Swift has become one of the biggest pop stars on the planet. Ever since her debut single "Tim McGraw" in 2005, Swift has taken the music world by storm bringing in multiple Grammys and CMA Awards and becoming a fashion and music icon in the process.
Videos by Wide Open Country
Swift's family moved her to Nashville when she was just a teenager to pursue a music career, and she's been unstoppable ever since. As a child, she knew this is what she wanted to do after watching a documentary about Faith Hill. After relocating with her family and trying to get a label's attention with her demo, she was discovered by Dreamworks executive Scott Borchetta while performing at the famous Bluebird Cafe. Borchetta signed Swift to his new independent label, Big Machine Records, and helped her release her self-titled debut album.
Swift was able to tap into the "teen country fans" market and became an overnight success with her albums full of songs that she either co-wrote or completely penned herself. Despite her transition from country music to pop, the superstar has not completely turned her back on her country roots. In 2017, she won a CMA Award for writing Little Big Town's "Better Man," which won song of the year. She was also featured on Sugarland's 2018 hit, "Babe." Not to mention she's in the process of re-recording all of her old albums and the Taylor's Version cuts of Red and Fearless were instant hits.
1. "Love Story"
The lead single from Swift's 2008 album Fearless, "Love Story" was inspired by the timeless story of Romeo and Juliet. Though the song peaked at number four on the Billboard Hot 100 charts, it is still one of her signature songs and one of the most downloaded to date. The music video won video of the year at the CMA Awards and CMT Music Awards. Fearless even won four Grammys, making Swift the youngest recipient of Album of the Year.
2. "Tim McGraw"
Her debut single hit No. 6 on the country charts. Swift wrote the song during her freshman year of high school while anticipating the pending breakup with her senior boyfriend when he left for college. The music video won Breakout Video of the Year at the CMT Music Awards. Her first album led her to a multitude of opening act opportunities, including Tim McGraw and Faith Hill's joint tour, where she was able to perform this song.
3. "Our Song"
"Our Song," also from Taylor Swift, hit number one on the country charts, making the singer the youngest person to write and perform a number one hit on the country Billboard charts. Swift wrote the song for a talent show in high school about a boyfriend who she didn't have a song with. She included it on her first album because she remembered how much her classmates loved it.
4. "Mean"
From Swift's third album, Speak Now, "Mean" was an instant hit. It also won Best Country Song and Best Country Solo Performance at the Grammys. Swift has said that the song was written in response to people criticizing her for everything little thing she does.
5. "Fifteen"
From 2008's Fearless, "Fifteen" was written about the pain of teenage heartbreak inspired by her best friend Abigail Anderson's breakup during freshman year of high school. The song shows a different side to the singer since it's more emotional, while the lyrics serve as a caution to teenagers about the pain that comes with young love. The music video, nominated at the MTV Video Music Awards, even features Anderson playing herself as they recount the pain of her high school story.
6. "Begin Again"
"Begin Again" was one of the many strong songs off Swift's fourth studio album Red in 2012. The song is all about the pain of a breakup and how you have to get up and move on. There is pain and vulnerability in putting yourself out there again, and this song captures it perfectly. The ballad was nominated for Best Country Song at the Grammys and for Video of the Year at the CMT Music Awards.
7. "You Belong With Me"
Easily one of the singer's most popular songs of all time, "You Belong With Me" was another successful hit from Fearless. She was inspired to write the song after hearing a friend argue with his friend on a phone call. The song became one of the biggest country-pop crossover hits since Faith Hill's "Breathe." The lyrics of the unrequited love story were perfectly captured in the music video of two high schoolers, winning music video of the year at the MTV Video Music Awards.
8. "We Are Never Ever Getting Back Together"
The lead single from Red became Swift's first number one hit on the Billboard Hot 100. It also topped the country charts for ten weeks. The song was first inspired when a friend of the singer's ex came into the recording studio talking about rumors that they were getting back together. Swift and her producers quickly came up with the catchy title, and fans were given the ultimate breakup anthem.
9. "Enchanted"
While this is one of Swift's songs that didn't reach the top of the charts, this song from Speak Now is one of her best ballads. It was inspired after meeting a man for the first time in New York, though his identity is unknown. Swift included the word "wonderstruck" that he had used in an email so he'd know it was about him.
10. "Should've Said No"
While her debut album was pretty much all gold ("Teardrops On My Guitar" anyone?), "Should've Said No" was Swift's second No. 1 hit for a reason. The lyrics are directed at a lover who cheated, and Swift wrote the song when she was 16 to cope with that craziness. She wrote the song overnight as a last-minute addition to the album. According to the singer, the lyrics were based on actual words she used to confront her boyfriend at the time.
11. "No Body No Crime" feat. Haim
"No Body, No Crime" is absolutely one of the standout tracks on Evermore. This country rock song follows a woman who confronts her cheating husband and gets killed for it. Swift brought in her longtime pals, Este, Danielle, and Alana Haim of the band Haim to join in the song since Este herself served as a bit of inspiration for the song's leading lady.
"Working with the Haim sisters on 'No Body, No Crime' was pretty hilarious because it came about after I wrote a pretty dark murder mystery song and had named the character Este, because she's the friend I have who would be stoked to be in a song like that," Swift told EW.
12. "Betty"
We know that Swift is the queen of writing about teen romance, and this song from Folklore is no exception. Using longtime friend Blake Lively's children's names for inspiration -- Betty, James, and Inez, "Betty" is told from the perspective of a 17-year-old boy, James, caught in a love triangle. He lost the love of his life after making a mistake and doesn't understand how to get back what he lost. As usual, Swift's lyrics perfectly capture the pain of lost teen love and some of the big life lessons you learn at that time in your life.
READ MORE: Taylor Swift's 'Tim McGraw': Who Inspired Her Bittersweet Debut?
Editor's Note: Products featured on Wide Open Country are independently selected by our editors. However, when you buy something through our links, we may earn a commission.
This article was originally published in 2020. It was updated in 2022.
