This Past Weekend w/ Theo Von – Episode #608: Jim Norton

Air date: September 5, 2025
Guest: Jim Norton
Host: Theo Von

Overview

This episode features comedian, radio icon, and podcaster Jim Norton in his first appearance on "This Past Weekend." The conversation runs the gamut: from the realities and quirks of podcasting and standup, to deep dives on personal relationships, sexuality, addiction, the comedy scene, and philosophical perspectives on self-identity and society. True to form, both Theo and Jim bring their trademark candor, sharp wit, vulnerability, and humor to a freewheeling, very human exchange.

Key Discussion Points

Podcasting Pet Peeves & Microphone Etiquette

• The episode opens with the two comics riffing about podcast annoyances—like guests who eat or chew gum on mic, dry mouth sounds, and self-awareness behind the microphone.
  • Memorable quote (Jim): “That sticky fruit roll-up sound. Yeah.” [02:07]
  • Both confess to their own podcasting faux pas and the anxiety of letting listeners down.

Aging, Self-Image, and Comedy

• Jim discusses body image, aging, and evolving self-perception:
  • “I went from mediocre to kind of shitty... I feel fat and just mushy and my neck is fat.” [03:31]
  • Theo notes that Jim seems to be growing into himself nicely, even as they both joke about losing their youthful spark.

Naming "Unconceivable" & Life on the Fringes

• Jim details the intent behind the title of his new special "Unconceivable," revealing layers of meaning related to both an archaic term and his wife’s infertility.
  • “It’s unconceivable on purpose. An old way of saying it. But also a nod to my wife who cannot conceive.” [05:08]
  • The duo riffs on dark, self-deprecating ways comics process being outsiders.

Memorable Nostalgia: The Shamokin Dunkin Donuts Saga

• The hosts revisit a classic viral moment: a Shamokin, PA news segment featuring locals mourning the closure of a Dunkin Donuts, idolizing the personalities involved.
  • “A lot of my friends go in there, get the cold coffee, iced coffee, I guess it’s called.” [08:07, Edna Faust]
  • This quirky story exemplifies how odd internet ephemera bonds the comedy community.

Jim Norton’s Marriage & Navigating Commitment

• Jim opens up about marrying a trans woman after a 90-day fiance visa, living in Montreal during the pandemic, and adapting to married life.
  • “You fight different when you’re married, because you can’t just go, fuck you, get out.” [10:24]
  • Both discuss past struggles with relationships, self-sabotage, and intimacy.

Understanding Sexual Orientation and Attraction

• In a frank, nuanced discussion, Jim explains his attraction to trans women, facing societal judgment, and how sexuality often defies categories.
  • “I don’t have the answer... It’s a pull, you don’t choose what direction you get pulled in.” [13:28]
  • Talks about the curiosity and questions he gets from men, including fighters, and stresses living authentically.

Relationship Strengths: Humor, Acceptance, & Transparency

• Jim celebrates how his wife’s humor and confidence allow him to be candid about their relationship on stage:
  • “She loves the stuff I talk about, no matter how embarrassing… She doesn’t give a fuck.” [17:59]
  • Importance of self-acceptance and not living for others' approval.

Comedy, UFC, and the Urge to Be Seen

• Jim discusses his UFC Unfiltered podcast with Matt Serra, paralleling fighters, comics, and strippers as people compelled to “show something private and want them to like it.” [23:14]
  • Commentary on why applause breaks don’t move him—only genuine laughter matters.
  • Praise for comics like Louie CK and insight into standup craft.

Mental Health, Addiction, and Recovery

• Both comics get candid about issues with porn, sex addiction, loneliness, and emotional maturity.
  • “I hate the way I feel the next day [after watching porn]... I feel kind of dissolved.” [37:25, Theo]
  • “That’s addiction. Sex is hard... porn, I still struggle with it.” [37:53, Jim]
  • They explore the “hunt” and ritualistic aspects of addiction vs. authentic intimacy.

On Growing Up and Identity

• The conversation delves into how comedy can delay emotional growth and the pros/cons of not following the conventional “adult” path.
  • “When you’re not following the pattern... you always feel like the end is not directly in front of me.” [41:30, Jim]
  • They discuss the challenge of finding and owning one’s identity in a noise-filled, judgmental world.

Kids, Family & Generational Shifts

• Theo expresses a desire for kids as a way to serve something beyond himself; Jim’s content without but supportive if his wife wants to adopt after he’s gone.
  • “I have nothing against it... But when I hear somebody who wants them, it supposedly opens up a part of you.” [44:23, Jim]

Sex, Society, & Changing Attitudes

• Addressing sexual taboos, hypocrisy among moralizing public figures, and societal evolution.
  • “But the majority who are scolding... in DC these prostitutes are going, do you know how many of these senators I fuck?” [31:33, Jim]
• Hilarious, offbeat banter about Mayflower sexual dynamics, shame, and repression.
  • “You gonna tell me Miles Standish didn’t get his asshole played with?” [32:24, Jim]

Honest Look at Friendship, Masculinity, and Emotional Bonds

• Vulnerable discussion on missing male affection and friendship, parsing the difference between homosexual attraction and deep platonic love.
  • “There's a moat between... loving a friend and wanting to peck them on the neck, for sure…” [62:18, Jim]

Political/Nuanced Takes

• Jim and Theo discuss polarization, groupthink, and the dangers of purity testing and conformity in politics and comedy.
  • “They’re joiners, masquerading as brave truth-tellers. It’s annoying.” [27:29, Jim]
  • “People give themselves the ability to go through information intelligently, but they think the rest of the public can't.” [117:19, Jim]
  • Praise for Trump’s sharpness and the privilege of interviewing world leaders, regardless of personal politics.

Comedians Supporting Comedians

• Both reflect on the importance of receiving encouragement from comics and even staff early in their careers.
  • “...the bartender said, hey, man, you did a good job. And just something like that little kept me coming back for the next two months.” [109:22, Theo]
  • Jim underscores not tearing down others just for social climbing or virtue signaling.

Reflections on Fame, Meeting Idols, and Humiliation

• Both share stories of meeting celebrities (and mistaking regular people for them), the strangeness of status, and their own embarrassing moments.
  • “I realized it was a Johnny Depp impersonator… Stupid, no show biz Jim Norton.” [95:35, Jim]

Kill Tony, Modern Standup, & New Comics

• Jim is celebrated as a standout guest on Kill Tony, and both dissect why the show works: honesty, pressure, and fairness in the process.
  • “If you could survive in that... If you're just doing the Mothership, you still know how many people are going to see it… If you're good, he’ll acknowledge you as being funny…” [112:48, Jim]

Notable Quotes & Memorable Moments

• Jim Norton, self-deprecating on his special's title:
  “If it was about me and my existence, I would have called it ‘should have been a load in a sock’.” [05:47]

• On attraction and the spectrum of sexuality:
  “You don’t choose what direction you’re going to get pulled in…something hits me and I lock into it.” [13:28 – Jim]

• Theo, on comedy stunting adulthood:
  “When you're comedian, you don’t ever have to grow or…I’ve struggled at certain points in my life to grow up.” [41:06]

• On being comfortable discussing being with a trans partner:
  “I have fun with her. She’s my favorite person. She’s the person I should have married. Do I get guys who are curious? Yes...I don’t talk about it in some serious...like, nobody wants to be scolded. Just be with whoever you like.” [20:03 – Jim]

• On addiction and ritual:
  “The ritual for me was looking and talking [to prostitutes]…Sometimes it’s the whole idea of doing something even more than doing it.” [36:21 – Jim]

• On seeking validation/friendship:
  “There was a part of me, for a little bit, [that thought] ‘is this a gay thing, or is this just a friend thing?’” [61:34 – Theo]

• On politics and performative outrage:
  “These purity tests are just one more way for people to climb the ladder. They give you a purity test, you fail, they climb a little higher because they gave the test. It’s nonsense.” [116:31 – Jim]

Timestamps by Topic

• [01:05] – Podcast etiquette, mics, and pet peeves
• [03:00] – Aging, self-consciousness, body image
• [05:08] – The meaning behind "Unconceivable"
• [07:00] – Shamokin Dunkin Donuts news clip
• [10:17] – On marriage, living together, changing as a partner
• [12:26] – Jim’s wife is transgender: what it means, societal views
• [13:28] – Attraction, sexuality, and living authentically
• [16:11] – Moving to Montreal during COVID, relationship test
• [23:14] – Comedy, UFC and the need for attention/validation
• [35:26] – Intimacy, addiction, pornography
• [41:29] – Growing up, resisting “adulthood,” and identity
• [44:23] – Kids, family, adoption
• [51:14] – Inflection point: a cocaine-fueled night leads Theo to recovery
• [66:35] – Jim discusses being bullied for his sexuality
• [109:07] – Importance of encouragement, camaraderie in comedy
• [111:08] – Kill Tony as a stand-up phenomenon
• [117:23] – People and personal responsibility when interpreting information
• [123:12] – On resisting temptation and staying “good” on the road

Tone & Final Thoughts

The episode is candid, bawdy, funny, and often movingly honest. Jim Norton’s willingness to discuss taboo subjects—from sex addiction and being married to a trans woman, to his relationship failures and cravings for acceptance—is matched by Theo’s earnest, probing nature and gift for finding both the comedy and emotional core of any subject. Both comics champion authenticity, resilience, and the importance of community, showing deep empathy beneath their irreverence. This is a must-listen for comedy fans and anyone interested in how artists wrestle with vulnerability, identity, and self-acceptance.

Watch Jim Norton's special "Unconceivable" now on YouTube and check out his podcast "Jim Norton Can't Save You."

This summary captures the key highlights, philosophy, and humor in the wide-ranging conversation, offering a window into the minds and hearts of two of comedy’s most introspective and unfiltered voices.