This week, Sequoia, Jewel and Ryann revisit Taylor Swift’s self-titled debut album in honor of its 20th anniversary. They look back at teenage Taylor’s country music beginnings and early hits like “Our Song” and “Teardrops on My Guitar.” Plus, did Taylor have a real country accent? Why hasn’t her songwriting evolved beyond high school heartbreak? Is she actually upset that we don’t like her? And why is it so hard to be a Black Swiftie? They also get into the “Picture to Burn” controversy, the boyfriends who inspired her best breakup songs (like Jake Gyllenhaal and “All Too Well”), her reputation as a bad style icon, and whether her debut album still holds up 20 years later. Tune in for a jam-packed episode full of hot takes, mid-2000s nostalgia, and the Taylor Swift discourse you’ve been waiting for!
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