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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This week, Sequoia and special guest and comedian Ify Nwadiwe celebrate the 20th anniversary of My Chemical Romance’s iconic rock opera concept album, The Black Parade. They unpack the album’s legacy, Gerard Way’s powerful voice, and why its messages about life and death—especially through “The Patient”—still resonate today. Plus, is “Welcome To The Black Parade” the band’s best song? Does “Teenagers” hit differently as you get older? And did The Black Parade help make emo culture mainstream? They also discuss whether Disney rock acts like the Jonas Brothers were a stepping stone to more traditional rock music, what it was like growing up as Black emo kids, and how My Chemical Romance compares to Paramore, Fall Out Boy, Panic! At The Disco, and Green Day. Tune in for a jam-packed episode fit for the album’s 20th anniversary!

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This week, Sequoia, Jewel and Ryann celebrate Insecure 10 years after the hit HBO series premiered. They get into the messiness of your late twenties and adult friendships and, of course, Issa and Lawrence’s complicated relationship history. Plus, was Insecure written for Black Twitter? Who was the best match for Issa—Daniel, Nathan, or Lawrence? Was Molly secretly jealous of Issa? And what did the show get right (and wrong) about sex, mental health, and friendship? They also debate whether Los Angeles is a character, where Insecure ranks among other ensemble female comedies, and break out the mirror raps one more time. Tune in for a mega-sized episode fit for the show’s 10th anniversary!

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