60 Songs That Explain the '90s

The Ringer

  • 1 hour 33 minutes
    Bruce Springsteen — “The Rising”

    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

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    18 February 2026, 7:39 pm
  • 1 hour 36 minutes
    Britney Spears – “Toxic”

    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

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    11 February 2026, 11:00 am
  • 1 hour 42 minutes
    “Buy U a Drank”— T-Pain

    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

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    4 February 2026, 1:00 pm
  • 1 hour 42 minutes
    “Hallelujah” — Jeff Buckley

    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

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    3 December 2025, 11:00 am
  • 1 hour 36 minutes
    “A-Punk” — Vampire Weekend

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    20 August 2025, 10:00 am
  • 1 hour 24 minutes
    "Grindin’"— The Clipse

    This week, Rob explores the biblical complexities of brotherhood throughout popular song, and uses those musical examples to highlight this eternal dichotomy: Some days when you aren’t Abel, there is always Cain. This sentiment rings glaringly true as he dissects the career of Virginia brothers The Clipse and their massive 2002 hit ‘Grindin’’, arguably the Neptunes finest production moment. Later, Rob is joined by Ringer alum Shea Serrano to explain why Malice and Pusha T’s elegant street poetry transcends the simple ‘coke rap’ designation critics have hastily assigned to their legacy.

    Host: Rob Harvilla
    Guest: Shea Serrano
    Producers: Chris Sutton, Olivia Crerie, and Justin Sayles

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    13 August 2025, 3:34 pm
  • 1 hour 32 minutes
    “Heavy Metal Drummer”—Wilco

    In this week’s episode, Rob uses the blueprint he learned from all of his favorite rock band movies, like 'Dig!' and 'The Great Muppet Caper,' to better understand the self-proclaimed misunderstood band Wilco. He takes us through Jeff Tweedy’s journey, starting with Wilco’s predecessor Uncle Tupelo, which diverged from the marketable grunge movement of its time to make forthright folk music. Unsurprisingly, Tweedy continued not to write music for the masses and the labels, inadvertently making hits like “Heavy Metal Drummer.” Later, Rob is joined by Dylan Tupper Rupert, who explains how she discovered Wilco as a 12-year-old and how a band can make even the most childless of listeners feel like a dad (in the best way).


    Host: Rob Harvilla

    Guest: Dylan Tupper Rupert

    Producers: Olivia Crerie, Chris Sutton, and Justin Sayles

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    6 August 2025, 10:00 am
  • 1 hour 40 minutes
    "The House That Built Me"— Miranda Lambert

    This week, Rob shines a light on the many ways singer-songwriters have utilized the concept of the word ‘home’ to convey where the heart and the human spirit truly reside. These musings serve as a springboard for a thorough analysis of country superstar Miranda Lambert’s hit song from 2010 ‘The House That Built Me’, and the defiantly authentic discography that preceded it. He’s then joined by friend and culture writer Elamin Abdelmahmoud from CBC’s ‘The Commotion’ podcast to expound further on Lambert’s infectious Texas charm.

    Host: Rob Harvilla
    Guest: Elamin Abdelmahmoud
    Producer: Chris Sutton, Olivia Crerie, and Justin Sayles

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    30 July 2025, 10:00 am
  • 33 minutes 29 seconds
    “Live Like You Were Dying”— Tim McGraw

    This week, Rob puts his pretensions about country music aside with a closer look at Tim McGraw’s simple but moving song, “Live Like You Were Dying,” that encourages even the most sarcastic of 20-something-year-olds to romanticize their life. He talks about his late father-in-law who shared the same zest for life as the song’s narrator, and he encourages all his listeners to go sky diving, rocky mountain climbing, and to share a song they love with someone they love.


    Host: Rob Harvilla

    Producers: Olivia Crerie, Chris Sutton, and Justin Sayles

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    23 July 2025, 3:05 pm
  • 1 hour 41 minutes
    “Ms. Jackson”— Outkast

    Why would the best ever want to stop being the best? Rob tries to figure this out in this week's episode covering Outkast. He proves that Big Boi and André 3000 will always be better together by comparing the tag team effort in their hit song, “Ms. Jackson,” and their split album ‘Speakerboxxx/The Love Below’. Later, he is joined by ‘Last Song Standing’ hosts, Cole Cuchna and Charles Holmes, to discuss how Outkast has aged for newer rap listeners and to share their favorite Outkast album in their self-proclaimed old age.


    Host: Rob Harvilla

    Guests: Charles Holmes and Cole Cuchna

    Producers: Olivia Crerie, Chris Sutton, and Justin Sayles

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    16 July 2025, 10:00 am
  • 1 hour 31 minutes
    “Can’t Stop”—The Red Hot Chili Peppers

    Rob initiates this week’s show by waxing poetic on the mortality of his musical idols and the treasure trove of emotional tribute songs that proliferated after the tragic passing of Nirvana frontman Kurt Cobain. His insightful homage leads perfectly into a loving soliloquy on the chaotic beauty of the Red Hot Chili Peppers' catalog, particularly their gigantic hit from 2002, “Can’t Stop.” Rob is then joined by both members of English pop duo the Ting Tings, who not only share his infatuation with bassist Flea’s instrumental prowess but also cite the RHCP's unbridled artistic vision as a major influence on their music.

    Host: Rob Harvilla
    Guests: Katie White and Jules De Martino of The Ting Tings
    Producers: Chris Sutton, Olivia Crerie, and Justin Sayles

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    9 July 2025, 1:00 pm
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