The Best Songs From Taylor Swift’s Older Albums

taylor swift

taylor swift is arguably the biggest artist of her generation. But she’s also one of the most empathetic. She knows exactly what it’s like to be a woman in the public eye, to be a pillar of pop culture for a generation, and to deal with the whirlwind that comes with it all.

The arc of a star like Taylor Swift is never a straight line, but it’s hard to deny her meteoric rise over the past decade-and-a-half. She moved from Big Machine to Republic Records, she directed music videos, she even took on acting roles (alongside some of the biggest names in Hollywood). And despite her erratic behavior in recent years—she sparked controversy when she accused her political opponent of lying about an alleged affair—she still managed to sell millions upon millions of albums and dominate dozens of music festivals worldwide.

It’s no wonder that a resurgence of popularity in her older material has fueled the perception of a comeback queen, one who’s learned to ride the wave of public attention rather than fight against it. Her sixth album, reputation, was her most successful to date and it spawned her first No. 1 hit in a decade, “Look What You Made Me Do.” But while there are plenty of singles and songs to enjoy from this era, some of the best taylor swift tracks are found deep in her catalogue.

While her most recent releases are more pop-oriented—2019’s Lover and 2022’s Midnights both topped the Billboard 200—it was the two albums released in 2020, folklore and evermore that really turned up the romance. Released in the middle of the COVID-19 pandemic lockdown, the duo of ruminative indie folk albums showcased new collaborators—including Aaron Dessner from The National and Jack Antonoff, as well as Bon Iver’s Justin Vernon—and tapped into the popular mood of isolation and despair.

It’s interesting to see the way in which this era of taylor swift’s career—which saw her taking on the major streaming services over the way they paid artists for their work—also yielded some of her most heartwarming music. The ode to her grandmother and their close relationship, for example, feels like a throwback to the days when Taylor was just starting out and her grandma’s advice still rang true for her. And while the song “Blank Space” and its accompanying music video feel like a departure from the rest of the album, it’s actually a great reminder that Swift is always willing to take risks in pursuit of what she truly wants.