Lovett or Leave It: “What a Year” (Best of 2025)

Podcast: Lovett or Leave It | Host: Jon Lovett (Crooked Media)
Episode: What a Year | Date: December 20, 2025

Episode Overview

This “best of” episode looks back at Lovett or Leave It’s wild, exhausting, and hilarious 2025 season. Host Jon Lovett and a cast of favorite guests and writers revisit the funniest, strangest, and most memorable moments—from absurd right-wing culture war panics to the collapse of late-night TV and the simple joys (and disputes) of relationships. Standout guests include Bob the Drag Queen, Roy Wood Jr., Tig Notaro, Stephanie Allen, Andy Richter, Henry Winkler, and more. The show leans into both the political weirdness of the year and the healing power of irreverent comedy, with Lovett’s trademark self-deprecating wit and frank discussions on everything from gay TSA beams to dog poop etiquette.

Highlights & Key Segments

1. Looking Back on a Chaotic 2025

Main Theme:
Lovett opens by reflecting on the “1,000 years long” that was 2025—emphasizing the need for humor in the face of political and cultural chaos.

• “Is this the end of American democracy? Has the social contract been irrevocably broken? And most importantly, do white jeans make you gay? The answer to all of those questions is we don't think so.” (01:22)

[00:00–01:30]

• Lovett lays out the episode’s premise: a “best of” lover’s choice, with reactions to heavy headlines and goofy culture war flare-ups.
• Guests: Bob the Drag Queen, John Marco Cerese, Roy Wood Jr., Tig Notaro, Stephanie Allen.
• Tease for “Sandwich of Justice” with writers Sarah Lazarus & Hallie Kiefer.

2. “Look Over They Them There”: Culture Wars Absurdities

[01:55–14:10]
Segment Highlights:

• Satire of right-wing panic over gender/sexuality:
  • “The claim that sitting in front of a screen makes you a woman.”
  • The body-scanner “gay beam” conspiracy.
  • Whether men can wear white jeans.

Notable Quotes:

• Roy Wood Jr.: “That man knows the flavor of penis… That is dick.” (03:49)
• Stephanie Allen: “No, because they shit themselves so much.” (12:10, on men wearing white jeans)
• Roy Wood Jr.: “White jeans are high risk, high reward, for sure.” (13:05)
• John Lovett: “Maybe the TSA body scanner turns you gay.” (10:14)
• Stephanie Allen: “I can’t. I’m sorry. I just can’t take it.” (10:57)

Memorable Tangents:

• Fast food beverage rankings devolve into affectionate debate about Diet Coke and Mountain Dew Baja Blast (05:56–07:41).
• Running joke: Lesbians don’t wear white jeans. (“If I see it, I’ll say, not a lesbian. You can’t fool me, bitch.” – Roy Wood Jr., 13:49)
• Ari Schwartz and John Lovett discuss their relationship dynamic and Jewish identity.

3. Vegan Poop and Dog Park Ethics (with Andy Richter & Paula Poundstone)

[14:32–17:24]

• Stormy debate: Can compostable poop bags go in yard waste? (Spoiler: No, because poop isn’t compostable—unless you’re a horse.)
• Andy Richter’s confession: “I would say that the reason I wasn’t putting human waste in the yard waste bin… is not because I knew I couldn’t… it’s just simply that I wouldn’t.” (15:47)

4. The Newlywed Game: Lovett, Ari, Tig Notaro & Stephanie Allen

[19:46–33:41]
A heartwarming—and occasionally cutting—group dynamic emerges while couples try to match “most annoying habit” and “most likely to ruin a vacation.”

• Stephanie Allen: “I gave Ari some suggestions backstage. I’m not gonna lie.” (26:31)
• Roy Wood Jr.: “What a nasty fight.” (28:20, on dog poop-picking technique)
• Tig Notaro sums up: “My body has failed me a few times.” (30:02)

Notable Quote:

• John Lovett: “There’s no amount of testosterone that can kill the part of a Jewish woman that wants a big diamond.” (21:57)

5. Henry Winkler: On Insecurity, Dyslexia, and the Fonz

[34:08–40:30]
A candid, moving segment where Henry Winkler shares his journey:

• Struggles with family support, academic difficulties, and dyslexia:
  • “My parents were really not supportive at all. They would call me Dummerhunt, which means dumb dog.” (35:57)
  • “I am in the bottom 3% academically in America.” (35:58)
• Finding meaning and self-acceptance in his later years:
  • “It is only in the last 10 years, I saw myself as a block of Swiss cheese filled with holes. And in the last 10 years, I have tried to make myself into a block of cheddar.” (36:20)
• Authoring children’s books, inspiration for Hank Zipser (38:56).

6. The Future of Political Comedy & The Collapse of Late Night

[43:17–59:57]
A raw, sharp analysis on:

• CBS canceling The Late Show with Stephen Colbert, after a Trump settlement:
  • Roy Wood Jr.: “You don’t do it like that if it’s about budget.” (50:45)
• The economics of late night, rise of podcasts, and the South Park/Paramount+ $1.5 billion deal.
• How comedy got more partisan under Trump, and the consequences.
• Lee I. Heisenberg:
  • “The problem with that is I did think you created a partisan late night that did turn off a lot of people… I think they should have been meaner to all people in power or more apolitical, one of the two you choose.” (56:23)

Notable Quotes:

• Gianmarco Cerese: “What you’re talking about is noble. It’s very noble. But it’s not maximum profit.” (58:56)
• “The moment you start isolating and you push people away and then you never bring them in… your entire audience are people who just are being pandered to and kind of get some steam off every night.” (Lee I. Heisenberg, 57:00)

7. Jewish Stereotypes & Family: “If the Jew Fits”

[62:48–69:31]
Rachel Bloom, Robby Hoffman, and the Lovett family lovingly dissect Jewish stereotypes (kvetching, temperature battles) and queerness.

• “To complain is to enjoy. To me, they’re one and the same.” (Sarah Lazarus, 62:48)
• Stephanie Allen: “My family… would have to restaurant hop if the restaurant was too cold.” (63:11)
• Generational stories about learning acceptance of LGBTQ family members:
  • “Some men love men and some women love women. They go, okay, it’s so fun.” (66:36)
  • “If you make it a big deal… They’re going to be screaming, crying.” (Sarah Lazarus, 69:11)
• John Lovett: “It’s almost like we need to take the whole conservative movement and just… show them a bunch of trans and gay people and just go, you’re okay. It’s no big deal. You’re okay.” (69:13)

8. Best Curmudgeons Game: Rank the New York Nudge

[69:34–78:49]
David Krumholtz reveals a rocky encounter with Danny DeVito, by way of a blind-rank contest for classic New York “curmudgeons” (Bernie Sanders, Fran Lebowitz, Larry David).

• “Danny DeVito fucking hated me and it was so bad that I had to quit.” (75:42)
• “He cursed me out one day… and my wife was pregnant with my first child and I had like all this insecure I was like, freaking out, and I was like—I need a break.” (76:01)

9. “Sandwich of Justice”: Writers vs. Lovett Joke-Off

[80:31–89:41]
Lovett, Sarah Lazarus, and Hallie Kiefer revisit a “Sandwich of Justice” bet where Lovett stubbornly insisted a convoluted joke would land—it didn’t.

• Sarah Lazarus: “I take pleasure in being right. I take pleasure in eating a sandwich.” (81:00)
• Lovett: “The joke bombed… And then you just keep mugging. You’re mug crazy.” (85:00)
• Dissection of joke mechanics, team chemistry:
  • “The beautiful magic between the three strange aspects of our personality…” (88:44)

Standout Moments and Quotes

• Lovett’s recurring bit on the year: “We came, we saw, we screamed, we laid down, we made some jokes and the some of them, dare I say many of them, even landed.” (00:22)
• On right-wing culture panic, Roy Wood Jr.: “Tariffs cure cancer. Tariffs gives you girlfriends. Tariffs gives you wings. Don’t drink a tariff after 3pm.” (08:45)
• Lovett’s reflection on comedy’s purpose: “I don’t know how I would have gotten through this year not being able to write jokes about what is happening. I feel like that is the function of this show for so many people, both who work on it and the listener.” (90:27)

Timestamps for Key Segments

| Segment | Timestamp | |--------------------------------------------------------|----------------| | Opening & Year Recap | 00:00–01:55 | | Culture Wars Segment: “Look Over They Them There” | 01:55–14:10 | | Vegan Poop Rant Wheel (Andy Richter, Paula Poundstone) | 14:32–17:24 | | Newlywed Game (Lovett, Ari, Tig, Stephanie) | 19:46–33:41 | | Henry Winkler Interview | 34:08–40:30 | | Late Night’s Demise (Colbert/South Park) | 43:17–59:57 | | Jewish Stereotypes & Acceptance | 62:48–69:31 | | "Curmudgeons": Ranking NYC Nudge | 69:34–78:49 | | “Sandwich of Justice” Segment | 80:31–89:41 |

Conclusion

Lovett or Leave It: What a Year gleefully wraps up a bruising 2025—showcasing the show’s strength as a cathartic, community-building engine of smart, pointed, and ultimately healing comedy. Whether tearing apart the latest political absurdity, picking over family foibles, or celebrating unlikely victories (and catastrophic joke failures), Lovett and friends remind listeners why laughter and honest conversation matter—especially when everything feels a little insane.

“Thank God for jokes and one sandwich.”
— John Lovett (90:44)