The 20 Best Taylor Swift Songs of All-Time

Taylor Swift

Taylor Swift was born on December 13, 1989, in Reading, Pennsylvania. Her first musical inspiration was her grandmother, a former professional opera singer. According to Biography, at 10, she was already singing at local fairs and entering singing competitions. A year later, she sang “The Star-Spangled Banner” at a Philadelphia 76ers game. Swift’s started her songwriting career at age twelve. Her family took her on frequent trips to Nashville, Tennessee, and during one, she performed at The Bluebird Cafe. Big Machine executive Scott loved her performance and signed her, releasing her first single a short time later. The self-titled album sold 5 million copies with the help of other singles like “Our Song,” which shot to number one.

The same year she won the Country Music Association’s Horizon Award and the Academy of Country Music Award for Top New Female Vocalist. In 2012, Swift topped Forbes’ list of the highest-paid celebrities under 30 with a net worth of 57 million. The following year, she donated 4 million dollars to the Country Music Hall of Fame in Nashville to create the Taylor Swift Education center, classrooms, and a learning lab. The singer knows how vital early music discovery is and how it fostered her career. Additionally, she believes songwriting isn’t something that can be taught in school because it’s such a unique art form.

During the opening years of Taylor Swift’s career, many wrote her off as a country music princess. However, over time she started writing more profound pieces. Her relationships may be notorious and almost seem like a way of getting new material. Yet, the singer has produced hit after hit and even given her some self-recognition. Even though Taylor Swift writes powerful songs that speak to the sadder parts of relationships and moments when we need to unleash or begin to realize our faults in relationships, some may call her songs cheesy or write her off as a pop princess. Love her or wish the airwaves would stop playing her songs; she has had many notable hits. These are the 20 best Taylor Swift songs of all-time.

20. Tim McGraw


According to Country Thang Daily, the song was the debut single on Swift’s first album in 2006. The same year she won the Breakthrough Video of the Year at the CMT Music Awards for Tim McGraw. The song’s lyrics speak to the relationships we worry are going to fade after disappearing. Much of the imagery is high school memories like nights that seem to go on forever. Additionally, it’s a tribute to memorable songs that will always hold a special place in our life. Even though some high school loves to turn into lifelong marriages, many more fade when we graduate and become adults.

19. Love Story


Even though many songs in Swift’s catalog are about guys, she dated with less than happy endings, “Love Story” is about someone her parents wouldn’t let her date when she was seventeen. According to Story of a Song, after being told no, she stomped off to her room and wrote this song, not knowing that later it would be a hit.

18. Bad Blood


According to Songfacts, this song is about Swift’s feud with another recording artist who tried to destroy one of her tours. Many people thought it was Katy Perry. Around the same time “Bad Blood dropped,” Perry was dating one of Swift’s ex-boyfriends, John Mayer. After Swift did an interview hinting at the identity of the person in the song, Perry tweeted. “Watch out for Regina George in sheep’s clothing.”

17. Today Was A Fairytale


Featured in the movie Valentine’s Day, the title ended up having a dual meaning since it broke the record for best first-week download sales by a female artist in February 2010. Additionally, it was the second American song to debut at number one on the Canadian Hot 100.

16. You Belong With Me


During an early songwriting session with long-time co-writer Liz Rose, Swift came in with the idea for the song after overhearing a conversation with a friend and his girlfriend. He was making excuses on the phone for having to end the call quickly. Swift was so upset, she put pen to paper and turned the experience into song gold. Even when people don’t treat us the way we expect, we can still do something different and make them like us.

15. 22


One of the best things a woman has is her group of friends. When Swift wrote this, she was starting her ascent into stardom and wanted to celebrate all the incredible milestones in the song. The singer dedicated it to friends Glee actress Dianna Argon and singer Selena Gomez. Later, Diet Coke Used it in a commercial. It’s also an excellent song for the over forty crowds who want to recapture some of their misspent youth.

14. I Knew You Were Trouble


How many people ignore red flags when they first start dating someone. Much of the song’s instrumentation sounds discordant, which Swift explained in an interview mirrored her feelings when she wrote it. “I Knew You Were Trouble” became Swift’s fiftieth song to hit the Billboard Hot 100, accomplished in just over six years to the day her first song “Tim McGraw” debuted.

13. Safe and Sound (Featuring The Civil Wars)


Swift co-wrote the song with Joy Williams and John Paul White as part of The Hunger Games soundtrack. T-Bone Burnett added to the minimalist instrumentation finishing it in a day. Although it’s part of a battle scene in the dystopian movie, the three artists created a soft song that speaks to many characters’ inner rage.

12. Cardigan


According to Nicki Swift, Swift’s latest album was a departure from earlier work because it didn’t contain signature tracks about relationships that left the singer heartbroken. “Cardigan” was the lead single. Many people thought the song was about the singer’s boyfriend, Joe Alwyn. However, the singer later posted it’s a song she wrote to her fans. The line “I knew you would come back to me” is about fans banding together with the artist during her negative press. Additionally, it’s about those who left during the Kanye West drama.

11. Begin Again


This is another highly relatable song from Swift’s catalog. When a relationship ends, many people retreat and decide not to date anymore, thinking they will never recapture the magic they once felt with another person and don’t want to be vulnerable again. However, when you open yourself to the possibility of falling in love again, you open yourself up to the start of something unique.

10. Everything Has Changed


Sometimes relationships fade because it’s difficult to recapture the first butterflies you feel when you begin the heady descent into falling in love. Additionally, you want to make a good impression and put your best foot forward. Many singers focus their lyrics on the later parts of a relationship, but Swift’s music speaks to the almost childlike wonder of meeting someone, getting tongue-tied, and thinking you might have met your person.

9. Back To December


According to Genius, the lyrics in the song are Swift’s apology to Valentine’s Day actor Taylor for breaking up with him. During an interview for his show Scream Queens, Lautner agreed he was the subject of the song. “Back to December” was Swift’s first piece to include orchestral instrumentation. It reached #6 on Billboard Hot 100. Additionally, it won two BMI awards, Publisher of the Year and Award Winning Songs. Swift also received appropriate recognition at the Teen Choice Awards, Choice Breakup Song. It’s a lot of acclaim for a song Swift later confessed was written on a napkin in an airplane bathroom.

8. Wildest Dreams


One-night stands are one of those things people don’t talk about, mainly because it leaves most people with feelings of regret and sometimes wishing things could have been different. It’s a much different take than other songs because it doesn’t focus on a relationship that ended but never happened. One standout on the song is the cadence of Swift’s heartbeats.

7. Pictures to Burn


Although this song doesn’t have the raw rage of a piece like You Outta Know by Alanis Morrissette, it speaks to women who don’t want to do jail time for getting revenge on an ex. The best line in the song is, “So go and tell your friends that I’m obsessive and crazy. That’s fine; I’ll tell mine that you’re gay!” Radio stations edited the line to the more politically correct “That’s fine you won’t mind if I say and by the way.”

6. Cold as You


Swift’s first album shows a depth in her music that was lost in a pop-country scene, radio-friendly songs until later in her career. Swift co-wrote the song with Liz Rose, someone she wrote many of her greatest hits. Despite only being sixteen when she recorded this song, she showed a maturity well beyond her years when singing this song. Later, Swift said this was her favorite song on the album.

5. We are Never Getting Back Together


Sometimes, instead of seeking revenge laughing at the insanity of our last relationship is a welcome panacea. Despite the overall campy feel of this song, it’s a great sing-along when you need to laugh at the end of a relationship instead of mourning how heartbreaking it is to lose the person you were dating.

4. Delicate


Despite Swift’s original image, later in her career, she received a lot of negative press. Unlike other songs, there is much hesitancy in this song, wondering if getting into a relationship is the best option with her turmoil. Despite the lyrics, many people think the song is about Joe Alwyn, her significant other, during the infamous Kanye West feud. The song is also for women who want to be in love but don’t want to let people know the darker parts of their past.

3. Last Time (Gary Lightbody)


The combination of Swift’s voice with Snow Patrol’s frontman Lightbody creates a haunting and powerful song about someone who’s finally ready to give up on a relationship that will never work. It’s one of Swift’s more heartbreaking songs. After all, it speaks to codependency and putting up with much more than we’d ever believed we would in a relationship.

2. Blank Space


Let’s face it; there are some seriously negative stereotypes about women in relationships. Additionally, women tend to gravitate to bad boys only to present themselves differently and then realize they’ve become the worst version of themselves. In this song, Swift sings about the sugar and spice every woman has but showcases in a way that gets people to look at their flaws humorously, so they don’t seem so negative.

1. All Too Well


Even though the studio version of this song is beautiful, Swift’s performance at the 2014 Grammys stripped down with nothing more than the artist and the piano captures the raw emotion and the heartbreak of losing someone we once deeply loved. Additionally, it’s a haunting reminder that memories of someone we once thought were the last person we would kiss and be with are only a song away. Many people suspect that the lyric “plaid shirt days” hints that the song is about Jake Gyllenhaal.

Final Words

Dave Grohl once said, “I don’t believe in guilty pleasures.” He went on to encourage people to admit they like something. Even though many people think they should feel guilty for listening to Swift’s music and write it off as a “guilty pleasure,” she is one of the most talented singers and songwriters of the last twenty years. Yes, her songs may not have the depth of more thought-provoking songs; they speak to a human and vulnerable side everyone has, and some don’t like to admit. So, the real “guilty pleasure” about Swift’s songs is indulging in cathartic emotional release or satisfying moments of hairbrush karaoke because many of her lyrics are so catchy you can’t help but sing along.

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