Lovett or Leave It – "Give Me Liberty, or Give Me Gutfeld"

Date: September 20, 2025
Host: Jon Lovett (Crooked Media)
Guests: Michaela Watkins, Colton Dunn
Location: Dynasty Typewriter, Los Angeles

Episode Overview

This episode kicks off the new season of Lovett or Leave It with Jon Lovett breaking down the week's absurd and troubling news, particularly the fallout from conservative influencer Charlie Kirk's assassination, the subsequent political and media reactions, and attacks on free speech. Lovett is joined by actor-comedian Michaela Watkins and actor-writer Colton Dunn for candid and comedic conversation on everything from trash TV to Hollywood labor and the challenges of activism in the streaming age. The episode closes with a round of affectionate tributes to living legends, emphasizing the need to celebrate icons while they're still with us.

Key Discussion Points & Insights

1. The Week’s News: Political Violence, Free Speech, and Media Crackdowns

(00:00–16:35)

• Charlie Kirk's Murder and Political Fallout:

  • Lovett opens with biting satire on Trump and Melania’s UK trip, Trump’s literary name-drops, and the distinctions (or lack thereof) he draws between thinkers like Tolkien, Shakespeare, and Orwell.
  • Shifts to the aftermath of Charlie Kirk’s death, dissecting how it has spurred renewed calls for a crackdown on dissent and vigilantism against “hate speech.” Notable conservatives like Stephen Miller and JD Vance are lampooned for advocating aggressive government action.
    • "With God as my witness, we are going to use every resource… to identify, disrupt, dismantle and destroy these networks and make America safe again for the American people. It will happen, and we will do it in Charlie's name." — Stephen Miller via Lovett (06:32)
  • Lovett urges the left to acknowledge the reality if political violence emerges from either side, but rejects collective blame tactics from the right.
    • "To do anything other than scream from the rooftops that this person does not speak for us is to act just a little bit like you've internalized the right's logic.” — Jon Lovett (06:20)
  • Critiques Attorney General Pam Bondi for over-broad “hate speech” crusades, later narrowed after criticism. Political absurdities are highlighted: hypotheticals about forced cake baking with Kirk’s image, radical bakers, etc.

• The Kimmel Precedent and FCC Threats:

  • Recaps how Jimmy Kimmel’s late-night show was taken off the air after FCC Chair Brendan Carr threatened action over on-air comments regarding Kirk’s death. Corporate cowardice leads affiliates to pre-empt Kimmel and even demand public penance.

    • "We can do this the easy way or the hard way." — Brendan Carr (12:31)

  • Lovett skewers both right-wing overreach and media conglomerates for spinelessness—"corporate cowardice on an absolutely mind-boggling scale” (42:16).

  • Satirical previews are offered of imaginary reactionary ABC programming, lampooning the dumbing down and politicization of network television.

2. Trash TV, Pop Culture, and the Hollywood Hustle

(19:09–35:19)

• Defending 'Hunting Wives':

  • Michaela Watkins admits to a complicated relationship with the Netflix hit “Hunting Wives”—a trashy, MAGA-laden, sex-filled drama about Texas wives—which she ultimately defends for its acting and guilty-pleasure appeal:
    • “Maybe you come for the hype about it and the tatas, but you stay for the really quality acting with really questionable material.” — Michaela Watkins (25:18)

• Brain Candy Shows:

  • Colton Dunn reveals his go-to escapist fare is “Emma Cruises” on YouTube, a British woman’s cruise review channel with a special focus on Diet Coke availability.
    • “Her big thing is whether or not they have Diet Coke on the cruise. She’s a big Diet Coke fan…She does not like fountain Diet Coke. She only wants Diet Coke from the bottle." — Colton Dunn (25:34)

• Wigs and Production Gripes:

  • An extended, tongue-in-cheek discussion of the bad wigs on “Hunting Wives” becomes a larger reflection on TV budgets, the shifting entertainment landscape, morale-killing labor climates, and the experience of actors in streaming-era productions.

• Coping with Political Despair:

  • Lovett channels the anxiety many listeners feel about U.S. politics and culture, expressing his own through recurring “spiky dreams” and comic descriptions of nighttime panic.

3. Culture Wars, Protest, and the Limits of Boycotts

(41:08–45:37)

• Should We Boycott Hulu/Disney?
  • As streaming services bend to political pressure, Lovett ponders: should liberals mount a serious, coordinated boycott? Guests debate the efficacy.
    • "If we're going to say, all right, this is the place. We're drawing the line. We're all going to cancel Disney. We're all going to cancel Hulu. It has to be both clear, serious. It has to actually have a goal.” — Jon Lovett (43:34)
  • Colton argues that cancellations directly hit streamers where it hurts, while Lovett cautions that success depends on focus and achievable demands.

4. Comedy Game: "Was I In This?"

(36:52–54:26)

• A recurring segment where Lovett quizzes guests on whether they were in various shows/movies—exposing obscure IMDb credits, cracking jokes about careers, and swapping behind-the-scenes stories (e.g., James Gandolfini anecdotes, hormone patches, and TV hair transplants).

5. Giving Living Legends Their Flowers

(56:37–66:52)

• Tributes to Hollywood Icons:

  • Inspired by the death of Robert Redford, the panel spins a “wheel” to celebrate still-living nonagenarians:

  • Shirley MacLaine:

    • Watkins shares near-miss stories of working with her and celebrates her enduring iconoclasm.
      • “She was never just… What's his face's brother Warren’s. She was her own whole damn thing.” — Michaela Watkins (60:17)

  • Dick Van Dyke:

    • Colton and Lovett salute his comedy legacy, lack of scandal, and universal appeal.
      • “Guy made tripping over an ottoman an icon.” — John Lovett (62:30)
      • “To rock the name Dick and like have it work. Never even connects with… And Dyke. He’s got it all in there.” — Colton Dunn (62:52)

  • Mel Brooks:

    • Lovett celebrates his unique combination of funny, positive, and Jewish sensibilities, recalling old Hollywood stories and the anticipation for “Spaceballs 2.”
      • “It’s a really funny, positive Jewish comedian. Wow, that’s a triple threat… Joyous, joyous.” — Jon Lovett (64:22)
    • Watkins shares having done a game show with Brooks and Cloris Leachman’s notorious on-set hijinks.

  • Panel reflects on Redford’s legacy—his roles, influence, and enduring “smoke show” status.

    • “He’s so hot it’s disturbing. Nobody should be.” — Michaela Watkins (65:49)

Notable Quotes & Memorable Moments

• On Political Violence:

  • “To do anything other than scream from the rooftops that this person does not speak for us is to act just a little bit like you've internalized the right's logic.” — Jon Lovett (06:20)

• On Corporate Cowardice/Free Speech:

  • "Corporate cowardice on an absolutely mind-boggling scale. Just people giving the administration rights it actually couldn't take, giving it power it couldn't seize and would never be able to win in court." — Jon Lovett (42:16)

• On Boycotts:

  • “Once you take yourself out of there, their whole business model is to figure out how to get you back.” — Colton Dunn (43:04)

• On ‘Trash’ TV:

  • “Maybe you come for the hype about it and the tatas, but you stay for the really quality acting with really questionable material.” — Michaela Watkins (25:18)

• On Anxiety and Politics:

  • “The eyes go down, and I'll try to take this thing down with a big old Xanax. Just a good old chemical… But the dreams, the spiky dreams, the anxiety, the points push through the cotton of the Xanax, poke through into the open air.” — Jon Lovett (45:11)

• Celebrating the Living:

  • “Why wait to have the feelings when they're gone?” — Jon Lovett (58:50)
  • “It’s a really funny, positive Jewish comedian. Wow, that’s a triple threat… Joyous, joyous.” — Jon Lovett (64:22)

Important Timestamps

• 00:00–01:19: Opening sponsor/FFRF plug and Lovett’s intro
• 01:20–16:35: Weekly news — Trump, Kirk’s murder, right-wing reactions, FCC-Kimmel saga
• 19:09–30:00: Comedy roundtable with guests, defending “Hunting Wives,” trash TV, bad wigs
• 30:01–35:19: Cultural snacking, hair transplants, Emmy speeches, political free speech debate
• 36:52–54:26: Game segment – “Was I In This?” (TV/film trivia and behind-the-scenes)
• 56:37–66:52: Celebratory “Giving Living Legends Their Flowers” and Robert Redford tribute

Tone and Language

The episode blends sharp satire, comic exasperation, cultural critique, and personal candor. Lovett maintains his trademark blend of earnest liberal anxiety and punchy, sometimes profane one-liners, with guests leaning warmly into self-deprecation and observational comedy. Jokes are often meta, with extended set-ups and audience/guest interplay reminiscent of live variety theater.

Summary for the Uninitiated

This episode is a must-listen for those seeking insight into the current state of U.S. media, free speech, and the escalated culture wars, all filtered through sharp comedic lens. It’s also an affectionate showcase of the messiness, humor, and solidarity found in both pop culture and political resistance—a place where trashy TV, personal anxieties, and robust debate all have a seat in the conversation.