Lovett or Leave It — "Ronald Reagan, Welcome to the Resistance"

Podcast: Lovett or Leave It / Crooked Media
Host: Jon Lovett
Guests: Steph Tollef, Daniel Webb
Date: November 1, 2025

Episode Overview

This Halloween-themed live episode is packed with signature Lovett or Leave It energy: rapid-fire takes on the week’s wildest and dumbest headlines, comedic debates about everything from AI erotica to household robots, and personal horror stories that double as dating advice. Lovett, joined by comedians Steph Tollef and Daniel Webb, tackles political absurdities under Trump’s third-term chatter, MAGA theatrics, and the bizarro direction of American governance, before letting the stage devolve into a laugh-out-loud therapy session about apps, assholes, and why you maybe shouldn’t get a taco tattoo for love.

1. "What a Week" – Trump’s Third Term & GOP Cowardice

[03:09 – 18:25]

Key Points

• Trump and Third Term Fantasies:
  • Steve Bannon and even Trump himself play coy about running for an unconstitutional third term, with Bannon calling Trump "a vehicle of divine providence."
    • "Divine providence. Maybe if God is named in the Epstein files at first." — Lovett [03:29]
• Constitutional Reality Check:
  • Lovett sharply reminds the audience (and Tommy Tuberville) the 22nd Amendment isn’t mere suggestion:
    • "The whole point of having a Constitution is that it’s actually not up to him. That’s what the Constitution is, a document that says it’s not up to him." — Lovett [04:32]
• MAGA Trolling Tactics:
  • Trump's refusal to rule out wild, lawless maneuvers is less about realistic plotting, more a mix of trolling and autocratic normalization.
    • "It's a joke and it's serious. But it doesn't matter how serious Trump is. What matters is how serious we are." — Lovett [06:09]
• Ongoing Trump Overreach:
  • Abuse of emergency powers (tariffs on Canada in response to an Ontario ad quoting Ronald Reagan anti-tariff rhetoric)
  • Lovett's recurring punchline: "Go off Ronald Reagan." [08:56]
  • Indictments against political opponents (progressive House candidate Kat Abu Ghazale), classified attacks on alleged drug traffickers without public evidence ("I know I'm always saying this on this show and I'm sorry to be repetitive, but go off Rand Paul." — Lovett [11:03])
  • Congressional complicity: quips about Speaker Mike Johnson's conduct and the absurdity of preventing new members (Adelita Grijalva) from being sworn in to block embarrassing votes.
    • "A bottom tries being a top and then holds a press conference..." — Lovett [05:50]

Notable Moments

• Lovett foreshadows a joke that “will require you to believe”—a meta-moment on live audience dynamics and comedic risk-taking. [06:09]
• Commentary on the existential dread of 2029 Trump:
  • "Presidential terms are like martinis. One isn't enough, two is too many, and three makes you puke and hug strangers on the train." — Lovett [06:09]

2. Government Overreach and Everyday Impact

[14:20 – 18:25]

Highlights

• "The problem isn't just that Trump wants to be a dictator. We live under a contract that contemplates would-be tyrants. The problem is that Congress is filled with spineless little freaks, and Trump knows that too." — Lovett [14:22]
• Examples of institutional decay:
  • Trump’s use of tariffs to punish allies
  • Suspension of SNAP benefits to pressure Democrats (with children and families suffering the real-life costs)
  • Federal election monitors sent to blue states as pretext for future voter intimidation

Notable Quotes

• "It only underscores why Democrats were right to draw a line in the first place... there are many ways in which we can lose even if we win. But the surest way for Trump and his allies to stay in power is to convince us that we cannot stop them. But that is just not true. At least not yet. And sorry if it is true by Saturday." — Lovett [17:30]

3. Segment: "Is This Good?" with Steph Tollef & Daniel Webb

[20:01 - 37:10]

A hilarious, lively debate segment where panelists must argue for or against new trends and tech—whether they believe in them or not.

Debate #1 — ChatGPT Erotica

[22:24 – 26:55]

• Pro (Steph):
  • Good for OnlyFans creators—let the robots do the work, human creators can finally get some rest.
  • "These gals can finally put their feet up and not be smothered by sick, disgusting, pervert pig men." — Steph [23:20]
• Con (Daniel):
  • AI-generated sexy content will never get human bodies quite right and could present safety issues ("I’m in immediate danger of electrocuting myself" — Daniel [24:35]).
  • On the educational upside: "It will help people learn to spell all the bad words." — Daniel [25:03]
• Lovett’s verdict: Daniel wins for the "danger of electrocuting myself" point.

Debate #2 — Airing Out Partners via Song (Lily Allen’s album)

[26:57 – 31:31]

• Con (Daniel):
  • “Straight white men need grace; the world is tough for them now.” (delivered with irony)
  • Steph explodes: Pro side is that public shaming is justified for cheating men.
  • "Are you fucking crazy? I'm sick and fucking tired of these white straight men cheating on all these fucking hot babes that are bringing in all the fucking money. Suck our fucking dick." — Steph [28:45]
• Daniel again declared winner, but the audience and Lovett agree Steph's side was more impassioned.

Debate #3 — $20,000 Home Robot (Neo)

[32:27 – 37:10]

• Pro (Steph):
  • Robots give time back to creators, could even double as a sexual companion: "Maybe put on a strap on. Who knows what I'm gonna do with the guy." — Steph [32:57]
• Con (Daniel):
  • Doesn't trust robots in the house, especially with shady remote operators, and wants design improvements: "Enough with the...is it a Sia music video? What am I watching? He obviously fences. But does he clean?" — Daniel [34:23]
• Steph wins this round for pitching practical and creative uses.

4. Dating Horror Shows, Halloween Edition: "28 Dates Later"

[39:55 – 57:48]

A riotous storytelling contest about truly terrifying dating experiences.

Memorable Stories

• "A man bit my neck mole off during sex." — Steph [40:31]
  • Required a trip to the “mole doctor” (dermatologist); audience howling at the gross and hilarious details.
• Daniel’s date trimmed bangs in the bathroom during a Grindr hookup:
  • "He cut bangs to blind himself so that he could just...without having to look at me." [47:10]

"Red Flag Dating Bracket" Game

• Least-bad options:
  • Offered $25 Chili’s gift card after sex ("This fucking slaps. What are you talking about? Are you kidding me? I love this." — Steph [48:14])
  • "Says their ex is crazy," "Doesn’t believe in sunscreen," “Being ghosted” all rate as manageable red flags.
• Undisputed worst dating scenario:
  • Getting matching tattoos; Steph recounts an agonizing, years-long removal process for a taco tattoo.
  • "That's 10 fucking sessions of my skin getting grilled off...Never get a matching tattoo with anybody in your life." — Steph [54:35]
• Runner-up horror:
  • Made to hold their gun after sex (Steph’s actual experience).
• Lovett sums up: The scariest dates are often right at the junction of poor judgment, mental illness, and weaponry.

5. Lightning Round: Biopic Details, Bruce Springsteen Hates Mustard, and Personal Truths

[62:47 – 66:19]

A segment riffing off the revelation that a new Springsteen biopic gets the Boss’s condiment preferences wrong.

Panelists’ Picks for Details to Get Right

• Steph:
  • “I don't actually hate my big labia...People tell me about labiaplasty, but honestly, my boyfriend doesn't mind it, I don't mind it, and men have never complained." [63:09–64:18]
• Daniel:
  • Wants his biopic to clarify that he is, in fact, on Lily Allen’s side. [64:42]

Notable Quotes

• "The surest way for Trump and his allies to stay in power is to convince us that we cannot stop them. But that is just not true. At least not yet." — Lovett [17:30]
• "People are complicated. Every once in a while, just to mix it up, a bottom tries being a top and then holds a press conference..." — Lovett [05:50]
• "Let's face it. Fuck. Senator Rand Paul said Congress had not been briefed about the attacks, nor has Trump presented any evidence as to whether the people killed were involved in drug trafficking." — Lovett [10:40]
• "Life is so short. And I think that’s kind of interesting. Cause it was a moment in time, and that’s who you were. And nothing to be ashamed about. You made your choice." — Lovett (to Steph, about her tattoo) [57:29]

Timestamps for Key Segments

• [03:09] – MAGA third-term trolling, constitutional analysis
• [08:56] – Reagan, tariffs, and the Ontario World Series ad
• [12:04] – Kat Abu Ghazale indictment, attacks on dissidents
• [14:22] – Autocratic creep, Congress as "spineless little freaks"
• [22:24] – “Is This Good?”: ChatGPT Erotica
• [26:57] – “Is This Good?”: Airing Out Partners in Song
• [32:27] – “Is This Good?”: $20K Humanoid Home Robot
• [39:55] – “28 Dates Later” Dating Horror Stories
• [54:35] – Worst dating horror: matching tattoos
• [62:56] – Minor facts biopics must get right about panelists

Final Thoughts

This Halloween installment is a perfect example of Lovett or Leave It at its best: trenchant, hilarious political comedy paired with disarmingly honest personal storytelling. Lovett’s eye-rolling through-line—reminding the audience how authoritarian creep mingles with dumb headlines—is interspersed with irreverent debates and comic stories that somehow link only fans, household robots, and tacos tattooed in the name of doomed love.

Don’t miss: Steph’s horror story about the bitten-off mole [40:31], Daniel’s bang-trimming hookup [46:02], and Lovett’s ongoing flirtation with meta-commentary on how to sell a joke to a nervous live crowd.

For more:

• Stand-up specials: Steph Tollef’s "Filth Queen" (Netflix), Daniel Webb’s live dates at thedanielweb.com
• CrookedCon details at crookedcon.com
• Subscribe for ad-free episodes and extras at crooked.com/friends