The Best Taylor Swift Songs Through the Eras

Anyone born between the years 1990 and 2000 has grown up with Taylor Swift’s music. Her songs poetically narrate the feminine experience, and her music has aged like fine wine with her audience. Even today, her music resonates with her now-grown-up audience.

It wouldn’t be fair to have only one favorite Taylor Swift song when she has an extensive discography backing her up. As a fan of Taylor’s music since I was twelve years old, here are her best works through the eras, based on lyricism and overall reception.

10. “Teardrops on My Guitar”

Taylor Swift (2006) made us all cry with her guitar and a boy named Drew. “Teardrops on My Guitar” is a song about unrequited teenage crushes, and even if you didn’t have a crush on anybody back when it was released or had any boy named Drew in your life, you probably took this song personally.

This is one of Taylor’s oldest songs, but every Swiftie out in the wild is eager to hear Taylor’s Version of this gut-wrenching classic.

9. “Love Story”

“Love Story” is a modern retelling of Romeo and Juliet. Even at nine years old, Taylor had me singing every word of this song as if I had a childhood crush I wanted to run away with. More than a decade later, Swifties are still singing the song’s chorus in unison whenever it plays in grocery aisles or on car radios.

Among all of Taylor’s songs on Fearless (2008), “Love Story” is the most recognizable, even by those who don’t consider themselves to be Taylor Swift’s fans. Unlike the classic by William Shakespeare, Taylor gives Romeo and Juliet a much happier ending in her song.

8. “Mean”

“Mean” stirred up controversy when it was released. Many assumed that this song was inspired by Kanye West’s actions against Taylor Swift in the 2009 VMAs. This was proven to be untrue, but it remained an amazing song about resilience against bullying.

Taylor Swift has several hits from her Speak Now (2010) album, and Swifties will forever be divided on which song on this album is the best, but “Mean” is special for having an inspirational narrative about overcoming bullying for the sake of your dreams. Plus, its country pop beat never gets old!

7. “All Too Well”

When “All Too Well” came out in Taylor’s version, ancient Swifties rose from their graves to play the ten-minute version in all its variations on a loop. The ten-minute version gives us more context about Taylor’s failed romance with one of her exes, which was even more heartbreaking than the original version of the song.

Red (2012) had a lot of heartbreaking songs with masterful lyricism, and it all boils down to which song is the fan-favorite pick. Even among all the sad girl songs on this album, “so casually cruel in the name of being honest” is a line that stings like no other.

6. “Blank Space”

This song was parodied to no end, but they all missed the point. Taylor was making fun of the media perception of her at the time as a serial dater on the verge of a breakdown, even if she was just a girl going on dates.

We at least have these people to thank for “Blank Space” from Taylor’s 1989 (2014) album, which remains a catchy beat today. But even if it’s a Taylor Swift parody by Taylor herself, “Blank Space” is a fun song about a whirlwind romance and a deadly woman. It was the Taylor Swift-gone-dark era, and we were all here for it.

5. “Getaway Car”

Forget what I said about going dark in the previous entry. Reputation (2017) was Taylor’s real dark era, where she artistically bit back against her critics and their vilification of her in the media. It’s become so popularized that you know somebody entered their “reputation era” when they stopped caring about what others had to say about them.

But among these songs, what makes “Getaway Car” the best? We never thought we needed Taylor’s take on Casablanca until “Getaway Car,” which sings about a doomed romance about two runaway fugitives. It looks like crime and romance just don’t go hand in hand.

4. “Cornelia Street”

Lover (2019) has many fluffy romantic songs, but no Taylor Swift fan is unfamiliar with the line, “I’d never walk Cornelia Street again.” Taylor has many memories of Cornelia Street, and even if we weren’t there to see it happen, the song makes us see them through Taylor’s perspective.

Cornelia Street is a perfect song that tries to encapsulate a moment and a person we never want to let go of. It’s such an iconic song that many Swifties get their pictures taken at Cornelia Street, which is located in New York City’s Greenwich Village.

3. “Cardigan”

Cardigan is a word that’ll remind you of Taylor Swift based on her fashion choices. But her song gives so much more sentimentality about a young, distant past lover who keeps the clothes of his exes tucked safely under somebody’s bed.

I’m not one to give sweaters or hoodies to lovers, but to be a favorite ex sounds like something incredibly fond. That’s what Taylor made us feel with “Cardigan,” so maybe you can forgive your ex for keeping your favorite jacket to themselves. They just can’t tell you they miss you.

2. “Champagne Problems”

Not everybody’s lucky both in life and love. Taylor’s “Champagne Problems” tells the story of a wealthy woman who couldn’t settle. The song was co-written by Joe Alwyn, whose relationship with Taylor ended in 2023.

There’s tragedy in loving somebody who wouldn’t choose you, and even if you might not have champagne problems, the feeling of inadequacy for a lover is a universal feeling when you think you’re dating somebody who’s “too good” for you.

1. “Anti-Hero”

Our biggest enemy could be ourselves, and Taylor’s “Anti-Hero” from her Midnights (2022) album showed that even Taylor has her own demons. “Midnights become my afternoons” is such a bop, but its openness about Taylor’s mental health struggles is what makes it open and raw.

Everybody has their own anti-hero within them, and it’s exhausting to have it win all the time. Taylor’s feeling of resignation is what makes this song extremely relatable, and it came perfectly during the sad autumn season, too.

(featured image: Taylor Swift Productions)