Happy Birthday, Taylor Swift! 13 Songs to Help You Understand the ...

A pop-music giant if ever there was one, Taylor Swift has had an astonishing year, what with her ultra-lucrative Eras Tour finally wrapping up; her 11th studio album, The Tortured Poets Department, breaking all manner of records; and the Recording Academy recently showering her with six more Grammy nominations. (She’s now been up for 58 in total, 14 of which she’s won.)

As she celebrates her 35th birthday today, Vogue is taking a long look back at—you guessed it—13 of the best, most memorable, and otherwise most important songs of Swift’s unparalleled career. Follow (and listen!) along below.

After signing with her first major label, Big Machine Records, in 2005, Swift had her first big hit with “Our Song,” the third single on her debut album. Written for a high-school talent contest, the song made her the youngest artist (aged 17 at the time) to reach number one on the Hot Country Songs chart.

Swift’s songwriting talents were later confirmed with Fearless, her Grammy-winning sophomore album, released in 2008. Among its biggest songs was “You Belong With Me,” in which the singer portrayed herself as the dorky secret admirer of a high-school classmate, himself obsessed with the most popular girl in town. Besides reaching number two on the Billboard Hot 100, the song also occasioned one of the wildest moments in pop-culture history. (A hint: “You Belong with Me” was up against Beyoncé’s “Single Ladies (Put a Ring on It)” for best female video at the 2009 MTV Video Music Awards, and Kanye West was not happy with the result.)

After the success of Fearless, Swift faced a wave of criticism, with some claiming she didn’t write her own songs. In response, she released Speak Now, her third album, which she composed entirely on her own. Infused with more rock energy than her previous works, the album aimed to establish Swift as a bona-fide songwriter. The track “Long Live” in particular served as a direct message to her fans, reflecting on her journey so far. (Swift was, at the time, all of 21.)

In the breakup ballad “All Too Well,” the fifth song on Swfit’s fourth album, Red, she addresses a former lover much older than herself, trying to understand the reasons for their setbacks. Already a fan favorite, the song—widely believed to be inspired by her brief relationship with Jake Gylenhaal—was re-released as a 10-minute epic in 2021, alongside a short film, starring Sadie Sink and Dylan O’Brien, directed by Swift herself.

2014 marked an important turning point for Swift, who, with her fifth studio album, 1989, finally went full pop. The shift had already begun with songs like “I Knew You Were Trouble” and “We Are Never Ever Getting Back Together” (both from Red), but it was with “Shake It Off” that Swift scored her first global pop hit. Nevertheless, “Out of the Woods” is the most memorable of 1989’s pop gems, ingeniously produced by Jack Antonoff, in his and Swift’s first-ever collaboration.

After Swift’s initial clash with Kanye West in 2009, tensions between them escalated further when, in 2016, West released the track “Famous,” rapping: “I feel like me and Taylor might still have sex. Why? I made that bitch famous.” Those lyrics did not sit well with the pop star—though the media firestorm that followed ultimately created more questions than it answered. Did Swift know about the lyrics before the song’s release, as Kim Kardashian suggested by sharing a snippet of a phone conversation between Swift and West? Was the recording edited to portray Swift as a liar? While the full truth never quite came out, Swift’s reputation suffered a major blow. Branded as manipulative, she faded from the public eye for a time…before making a powerful comeback in 2017, with Reputation’s “Look What You Made Me Do.” A direct response to the attacks, the song was accompanied by an iconic music video filled with references to those who had wronged her, including Kardashian and, for different reasons, Katy Perry.

Although perceived as a vindictive album, Reputation is also a sentimental one, with its fair share of love songs. Case in point? “Delicate,” a synth-pop ballad sprinkled with vocoder-driven vocals about the dawn of a new romance.

Following the end of her contract with Big Machine, her first label, Swift signed with Republic Records, a subsidiary of major label Universal Music, in 2018. After being painted as a singer with a permanently broken heart, Swift released Lover, the romantic title track of which is a standout. Produced by Antonoff, the song blends country and folk sounds, as if heralding the stylistic turn to come…

In the midst of the pandemic, with the whole world in lockdown, Swift unveiled her surprise eighth studio album. Soberly titled Folklore, it welcomed a new collaborator into her sonic universe: musician and producer Aaron Dessner of The National. With his and Antonoff’s input, Swift took a turn towards folk and soft rock on the album, matching minimalist productions to fictional narratives that borrowed from classic stories. The opening track, “The 1,” introduced Swift’s bold new mode: “I’m doing good, I’m on some new shit / Been saying ‘yes’ instead of ‘no,’” she sings. A few months after its release, Folklore would win the Grammy for album of the year.

Six months after Folklore came out, Swift unveiled Evermore, another surprise album, imagined as a counterpart to its predecessor. Carried by the same folk melodies and produced by the same people (namely, Swift, Antonoff, and Dessner), Evermore included an appearance from Este, Danielle, and Alana Haim. On “no body, no crime,” they join her in telling the story of an adulterous man’s doomed fate, doing some of Swift’s very best (and spookiest) storytelling.

Midnights, Swift’s 10th studio album, released in 2022, spanned intimate explorations of regret, longing, bitterness, and nostalgia. Yet it’s in the final song, “Mastermind,” that Swift is her most bravely transparent, painting herself as a veritable mastermind who plans her every move in advance, wanting only to be loved for who she is: “No one wanted to play with me as a little kid / So I’ve been scheming like a criminal ever since / To make them love me and make it seem effortless…”

Just three hours after Midnights came out, Swift revealed an extended 3am Edition, including the song “Would’ve, Could’ve, Should’ve”—easily among the songwriter’s masterstrokes. Produced by Aaron Dessner, the track—which recalls a love affair when Swift was 19—is built on a breathless drum beat and galloping vocal, gaining in intensity as it progresses.

Touted as a breakthrough album, The Tortured Poets Department, released in April 2024, is complex and intimate, reflecting Swift’s doubts in the light of her success and its consequences on her life. A double album, TTPD blends elements of both Midnights and Folklore, probing the tragic, the sublime, and the comic in equal measure. The song that closes the first part of the opus, “Clara Bow,” is a perfect example: Named for the 1920s comedienne, it allows Swift to build her own mythology, while excoriating the constant comparisons made between women in the entertainment industry. In particular, she invokes Stevie Nicks, who responded with a poem that Swift’s fans discovered when they bought the physical album.