60 Songs That Explain the '90s

60 Songs That Explain the '90s

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First came '60 Songs That Explain the '90s.' (We did that.) Then came '60 Songs That Explain the '90s: The 2000s.' (We're doing that now—and yes, that's the actual name.) But whether you want to jump back to the Clinton years or join us as we reboot our old iPods, you can find all of the collected works of Rob Harvilla below. Come back each Wednesday for a new episode.

Episode List

Bruce Springsteen — “The Rising”

Feb 18th, 2026 7:39 PM

In the uncertain moments following 9/11, we were searching for comfort and someone to help us make sense of it all. Today, Rob discusses the one musician who was capable of stepping up and capturing the emotions the American people were feeling: Bruce Springsteen. Rob recaps the political statements Springsteen had been making in the decades before, which prepared him for the creation of “The Rising.” Finally, he is joined by music critic and Springsteen expert Steven Hyden to discuss where the album ‘The Rising’ ranks in his discography. Host: Rob Harvilla Producers: Justin Sayles and Olivia Crerie Additional Video Editing: Kevin Pooler Guest: Steven Hyden Learn more about your ad choices. Visit podcastchoices.com/adchoices

Britney Spears – “Toxic”

Feb 11th, 2026 11:00 AM

Before he vows to leave her alone, Rob breaks down the cataclysmic career of a pop star who did it for the love of the game and the disgust of the fame. Britney Spears had the power to shift culture with a single VMAs performance, yet her music reflected a desperation to control her own personal life. Despite the public’s continuous mistreatment of Britney, she selflessly gifted us one of the most iconic bangers of our time: “Toxic.” Afterwards, Rob speaks with music journalist Jeff Weiss to talk about the unfinished evolution of Britney’s career, the difference in today’s celebrity culture, and creation of his book, ‘Waiting for Britney Spears,’ in the time of the Free Britney movement. Host: Rob Harvilla Guest: Jeff Weiss Producers: Justin Sayle and Olivia Crerie Additional Video Editing: Kevin Pooler Learn more about your ad choices. Visit podcastchoices.com/adchoices

“Buy U a Drank”— T-Pain

Feb 4th, 2026 1:00 PM

At long last, Rob has returned to your speakers and screens, triumphant in the face of his haters. In this way, he is no different than the subject of today’s episode: T-Pain. Even though he wrote, produced, and performed some of the greatest hits of the 2000s, T-Pain’s use of auto-tune overshadowed his talent. However, after his 2014 Tiny Desk Concert, it is safe to say we all owe T-Pain an apology (and a drank). Finally, Rob talks to The Ringer’s Tyler Parker, who speaks to the shock of hearing “I’m n Luv (wit a Stripper)” for the first time and becoming fascinated with T-Pain’s style and his version of the club. Host: Rob Harvilla Guest: Tyler Parker Producers: Justin Sayle and Olivia Crerie Additional Video Editing: Kevin Pooler Learn more about your ad choices. Visit podcastchoices.com/adchoices

“Hallelujah” — Jeff Buckley

Dec 3rd, 2025 11:00 AM

Today, Rob returns with a gift in time for the holidays, breaking down what many would call the voice of an angel. He takes us back to the ’90s, when one of the most covered songs on the planet was merely a forgotten, horny track from Leonard Cohen’s catalog. While many artists cover songs in an attempt to replicate the original (or just sing it more loudly), Rob explains how Jeff Buckley covered the song and made it new. Later, Rob is joined by documentary filmmaker Amy J. Berg to discuss her new project ‘It’s Never Over, Jeff Buckley.’ She describes the intimate moments of Buckley’s mother she captured, how Buckley’s father affected his relationship with success and music, and the difficulties of what to do with an artist’s unfinished discography posthumously. Host: Rob Harvilla Guest: Amy J. Berg Producers: Justin Sayles, Chris Sutton, and Olivia Crerie Learn more about your ad choices. Visit podcastchoices.com/adchoices

“A-Punk” — Vampire Weekend

Aug 20th, 2025 10:00 AM

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