Podcast Summary: The Nerve with Maureen Callahan

Episode: "How Timothée Chalamet, Taylor Swift and Other Celebs Try Too Hard To Be Cool and The MTV Revolution"

Date: December 3, 2025
Host: Maureen Callahan
Guests: Tom Freston (former MTV CEO), Elle Hunt (Guardian writer)

Overview

In this sharp, smart, and entertaining episode, Maureen Callahan examines the concept of "cool"—who has it, who desperately chases it, and why it's so elusive—through the lens of celebrity culture and media history. The show features a deep-dive interview with Tom Freston, the MTV exec responsible for some of pop culture’s most iconic moments, and a hilarious, insightful conversation with journalist Elle Hunt about a global academic study on what actually makes people cool. Maureen also reads audience feedback and riffs on everything from Van Halen to Taylor Swift to Timothée Chalamet's try-hard Ping Pong movie campaign.

Main Segments & Key Insights

1. The Rise and Fall of MTV with Tom Freston

[06:25–38:13]

The Legacy of MTV

• Maureen brings on Tom Freston, the co-founder and former CEO of MTV (and Viacom), to discuss his new memoir "Unplugged: Adventures from MTV to Timbuktu."
• Tom Freston on the Death of MTV's Cool Factor:
  “It like stumbled on the Internet. ... MTV was one of the networks that had, you know, sustained some of the most damage as its viewers were like, we were like the canary in the coal mine.” (07:32)
• MTV's transition from the epicenter of youth culture and music to reality TV filler is tied directly to the rise of the internet (“YouTube made the inherent problem for MTV’s original format... which was a linear television network... on demand is cooler than what you were doing, even though what you were doing for a long time was kind of cool and fun.” [36:14])

Iconic Moments

• The “Lost Weekend with Van Halen” Contest:
  Maureen and Tom relive the story of one of MTV’s earliest and wildest sweepstakes—a nerdy suburban kid plunged into rock debauchery, with little people as security guards backstage.
  • “You could never do this today. ... David Lee Roth would be cancelled for making fun of little people. ... That was giving the average suburban kid a real backstage pass.” – Maureen (12:48)

MTV Unplugged

• Nirvana's legendary unplugged show: Kurt Cobain thought he’d bombed due to the subdued audience, not realizing the performance’s cultural impact.

  • “To us, this was the way they wanted to express themselves... No one was going to stand up and say, 'Oh no, we’re not going to air that because it doesn’t meet our standards.'” – Tom (16:00)

• Tom’s favorite: LL Cool J’s Unplugged, “...it was a fusion of rock and hip hop and it was so electrifying. Everybody in the studio is punching the air. ... Mama gonna knock you out.” (17:01)

• Why Unplugged died: Corporate shift, music people left, budgets dried up—“They kind of walked away from music to the point where... they even took music off the bottom of the logo. They didn’t want anything to do with it.” (18:32)

MTV News

• Tom describes the birth of MTV News:
  “We could be a bigger place... if we were about some of the things, what the music was about, like fashion, news, sports... News was a key thing. ... We hired Kurt Loder and put in place a real news operation. ... We became a go-to place for news about popular culture.” (20:22)

Presidential Moments & Corporate Scandal

• Bill Clinton’s “boxers or briefs” exchange with the MTV audience, showing MTV's cultural reach.

  • “Mr. President, the world's dying to know, is it boxers or briefs?” – Classic clip [24:25]
  • “He had an hour of substantive conversations... But that’s the thing that the media seized on.” – Tom (24:28)

• Wild tales from MTV/Viacom’s corporate heyday, from record execs sending strippers to the office to Tom touring Bangkok sex clubs with Sumner Redstone.

  • “If a Page Six had gotten a hold of this ... what would have happened to Sumner? ... I don't know... it was at a different era.” (27:28)

The Loss of MTV’s Cool

• Maureen asks when MTV truly lost its cool:
  “Unless you’re like James Dean or Jimi Hendrix and you die really young, you’re always cool... I think when MTV began to lose its mojo was really with the birth of YouTube... The gatekeeper status that you had, the control over your audience, has disappeared...” – Tom (35:27)

2. What Is “Cool,” Anyway? With Elle Hunt

[51:04–79:04]

The Academic Study of Cool

• Maureen introduces Elle Hunt, Guardian columnist, who explored a rigorous, multi-country academic study dissecting the meaning of “cool.”
• Study looked at over 10 countries and dozens of cultural perspectives; found remarkable agreement about key traits:
  • “The attributes [for cool] were extroverted, open, hedonistic, adventurous, autonomous, and powerful.” – Elle Hunt (56:37)

Key Insights and Disagreements

• “Trying to be cool will only make you further uncool. Cool people don’t seem to express emotion.” – Elle quoting the study, but Maureen disagrees:

  • “I think you have to be an original.” – Maureen (59:12)

• Elle raises the rarely acknowledged role of physical attractiveness: “Being physically attractive really helps [with] being cool... If you’re not either of those things, it’s an extra disadvantage you’ve got to overcome.” (61:02)

• The paradox: True cool is about authenticity, not effort.

  • “You need some mystique to be cool... Kate Moss learned very early on and has largely stuck to [that].” – Maureen (66:43)

Cool vs. Try-Hard & Case Studies

• Maureen and Elle dissect modern celebrities’ attempts and failures at cool:

  • Taylor Swift: “She cares way too much what others think... and she does try to be all things to all people and she's swatty.” – Maureen (63:28)

  • Adam Levine: “He just reeks profoundly of uncool... That stink is still on him.” – Maureen (64:53)

  • Timothée Chalamet: Maureen roast his high-strung, try-hard Hollywood marketing meeting: “This is the opposite of cool. ... Timothy Chalamet, there’s bigger stuff going on than your little stupid ping pong movie.” (70:12)

  • The Royals, Harry & Meghan:
    “Whenever you start a company based on yourself... you think you’re cool, which automatically makes you uncool.” – Maureen (71:19)
    “They are two of the most profoundly uncool people on the world stage.” – Maureen (73:22)

A Memorable Quote

• “Cool people don’t give a shit what you think about them, including whether you think they’re cool or not.” – Maureen (75:22)

Cool Is Un-definable But Recognizable

• “We can only measure if people are perceived as cool. Cool is not a static or definable... quality. ... That’s what makes people want to chase it or possess it—because you can’t really ever buy it.” – Elle (74:32)

3. Audience Feedback Highlights

[41:21–48:42]

• Maureen reads and responds to humorous listener emails about A-Rod being “as fake as they come” [41:21], smoking in movies, and why Michelle Obama’s hair excuses for not swimming are “offensive” and “dangerous.”
• Zings Cheryl Hines for “dating Bobby while he was still married to Mary ... so fuck off. Okay? All the way off.” (47:34)

Notable Quotes & Timestamps

• On the MTV Awards’ fall:
  “It didn’t really land in the culture the way, I mean, it used to... You had to watch it live. You never knew what was going to happen.” – Maureen (08:31)
• On the death of creativity in legacy media:
  “Where the focus is not so much on creativity, but on cost cutting, data, and a lot of things that, you know, we didn’t have to deal with too severely when the business was ascendant.” – Tom Freston (34:04)
• On the myth of “cool people are always good”:
  “I don’t think the two have anything to do with each other.” – Maureen (54:50)
• On Taylor Swift:
  “She cares way too much what other people think and she does try to be all things to all people.” – Maureen (63:28)
• On the modern impossibility of celebrity cool:
  “It’s much harder in some ways to be cool in this time because celebrities... are expected to be so visible on social media... It’s very hard to retain that sense of mystery.” – Elle (65:48)
• On “coolness” as a paradox:
  “You know it when you see it, but it’s very hard to actually define or imitate.” – Elle (73:22)

Timestamps for Key Segments

• 06:25 – Tom Freston joins to discuss MTV’s history and influence
• 10:17 – “Lost Weekend with Van Halen” story
• 14:05 – Nirvana’s Unplugged taping and cultural impact
• 20:15 – The invention and legacy of MTV News
• 24:25 – The Bill Clinton “boxers or briefs” moment
• 27:28 – Scandalous corporate tales, including Bangkok sex clubs
• 35:27 – When MTV finally lost “cool” (YouTube effect)
• 51:04 – Elle Hunt on the science of cool, “Can I Learn To Be Cool?”
• 56:37 – Cool’s six core attributes (from the global study)
• 63:28 – Taylor Swift & Adam Levine dissected
• 70:12 – Timothée Chalamet’s “cringe” marketing Zoom
• 73:19 – Meghan & Harry: Why “trying to be cool” fails

Tone and Language

• Maureen’s tone is witty, bracingly honest, and occasionally acerbic.
• The show is irreverent, skeptical, and direct (“...so fuck off. Okay? All the way off.”).
• Guests match Maureen's intellectual and humorous vibe, leaning conversational and sharp.
• Heavy mix of personal anecdote, cultural critique, and pop psychological analysis.

Takeaways

• MTV’s “cool” was built on risk-taking, music culture, and breaking rules—a magic lost to corporatization, the digital revolution, and safe, sanitized reality TV.
• Cool can't be bought, manufactured, or studied into existence; authentic originality, autonomy, and a dash of rebellion are universally recognized components.
• Celebrities who try the hardest to appear cool (Taylor Swift, Timothée Chalamet, Adam Levine, Meghan Markle) are often the ones who miss the mark, underlining the paradox of cool: it’s only yours if you don’t declare it.
• Even as “cool” is picked apart by academics and culture writers, its very essence remains elusive, contextual, and eternally subjective.

Suggested Listening

If you want a crash course in pop culture’s shifting sense of “cool”—with plenty of sharp jokes and insider storytelling—this is a must-listen.