FITZDOG RADIO: Greg Fitzsimmons with Annie Lederman
Episode 1114 | October 29, 2025

Overview

Greg Fitzsimmons welcomes comedian and close friend Annie Lederman for a candid, hilarious, and at times deeply personal conversation. They riff on awkward medical procedures, family chaos, comedy club drama, personal growth, spirituality, trauma, sex, and surviving the stand-up grind. Both showcase their signature blend of brutal honesty and quick, biting wit, blending raw storytelling with comic catharsis.

Major Topics & Key Insights

1. Medical Mishaps & Middle-Age (01:08–18:00)

• Greg’s Colonoscopy Adventure:
  • Details the awkwardness and indignity of a colonoscopy, including a fanboy anesthesiologist, bidet rituals, making jokes while exposed, and dealing with Home Depot incompetence.
    • “You can’t go hard wipe on any of them. We have a bidet. Thank Lord Jesus Christ in heaven, who I believe invented the bidet…” (05:12)
    • “I treat my asshole like it’s a war protester in the 1960s. Hit it with the fucking hose, baby.” (06:15)
• Taking Pride in Avoiding ‘Manly’ Repair Jobs:
  • Greg admits he’d rather call in a real handyman than fix a toilet himself, even if his wife claims, “it’s two screws!”
    • “I tell jokes and I podcast. That’s what I do. And I make good money and we hire people to do [that].” (13:03)

2. Comedic Chemistry & Camaraderie (19:51–23:14)

• Old Friends, New Riffs:
  • Greg welcomes Annie, lauding her style and honesty. They bust each other up about quirks (Annie’s on-off sunglasses, family tics) and shared history working on Chelsea Lately, Trash Tuesday, and David Spade’s show.
    • On Annie’s glasses:
      “It’s a nervous tic. My brother has Tourette’s…this is my Tourette’s.” (20:48)

3. Family Dysfunction & Emotional Growth (22:02–27:17)

• Childhood Chaos:
  • Annie unpacks the explosive, tumultuous energy of her family:
    • Her twin brother’s Tourette’s, her dad’s non-violent screaming, and her mom’s chaotic parenting (“she’d press the gas [in the car] and say ‘why don’t I kill us all?’” 22:51).
  • Both reflect on how rage cycles and ego play out in comedy, and resisting the ego-driven urge to “pop off” at staff.
    • “I love in those moments, showing grace. But then when I don’t get…like, thank you for showing grace, then I have to be like, show grace to that.” (24:50)

4. Comedy Club Drama, Ego & Staying Grounded (23:36–31:56)

• Backstage Stories:
  • They recount run-ins with door guys who don’t recognize famous comics (even Bill Burr gets turned away).
  • Annie and Greg bond over resisting the urge to lash out, choosing “grace under fire,” and their ambivalence toward comedy’s competitive culture.

5. Best Buddies Benefit, Neurodiversity & Comics Community (28:51–32:22)

• Heartfelt Moments:
  • Both are visibly moved recalling the recent Best Buddies benefit for people with intellectual disabilities.
    • “It’s like an infusion of joy. People with no cynicism.” (29:25) – Greg
    • “They help people with intellectual disabilities. That’s why I’m a member. They’ve done so much for me.” (29:14) – Annie
• Norm Macdonald Anecdote:
  • Norm goes out of his way to connect deeply with a comic with Asperger’s, creating a beautiful, unguarded green room moment.

6. Woke Audiences, Traveling Comics, and Cancel Culture (34:34–37:20)

• Nuanced Views:
  • The two riff about the controversy over U.S. comics performing in Saudi Arabia, finding themselves amused or bemused by the outrage.
  • “Who’s this? Why do people suddenly pick things to get involved? Oh, now all sudden, you’re going to be political?” (33:04) – Greg

7. The Writer’s Block & Procrastination Game (34:38–36:46)

• Hacks to Productivity:
  • Annie confesses her lifelong struggles with procrastination, while Greg shares how dictating stories and paying someone to transcribe his book broke through his inertia.
    • “Writing is easy. Sitting down is hard.” (34:59) – Greg

8. Flakiness, Friendship & ADHD (39:06–41:37)

• Addressing the Elephant:
  • Greg gently probes Annie about her tendency to drop off communications, which they both interpret as classic ADHD.
    • “I don’t reach out to people, and then they think I’m mad at them.” (39:34) – Annie

9. Comedy Podcast Studios & Industry Inside Baseball (41:08–43:46)

• Podcast Hustle:
  • Annie talks about recording at multiple studios, the unwelcome attempts at club “ownership,” and the merits of working from home vs. showing up like a job.

10. Fan Q&A: Sexcapades, Celebrity Friends & “Most Improved” (43:50–78:57)

• Spicy Confessions:
  • Woodsy sex, accidental threesomes, and the perils of being a “comedy groupie.”
    • “I like banged this guy in the woods once, but I got a twig inside…I pulled out a twig later.” (44:46) – Annie
  • Discusses her “most improved swimmer” childhood award, and how it helped fuel her drive for self-improvement.
    • “It’s what I…felt like. It resonated with me as a kid. I was like, oh, I liked it because…it showed I liked progress.” (77:23) – Annie
• Celebrity Friends & Imposter Syndrome:
  • Anecdotes about Aquafina and Olivia Munn, Annie’s supportive role, and how success sometimes deepens self-doubt.
    • “I like really helped her…like she talks about me in interviews about how I helped her through this imposter syndrome. And then she like blew up, and then I got imposter syndrome.” (54:01) – Annie

11. Trauma, Resilience, and Spiritual Growth (80:44–84:11)

• Coping with Pain and the Past:
  • Annie opens up about trauma: family violence, molestation, a serious childhood car accident, and healing through openness, humor, and alternative spiritual practices.
  • On spiritual forgiveness:
    • “Every time you’re met with someone that bothers you, annoys you, feels toxic…oh, I actually called them in so I could overcome something.” (68:59) – Annie

12. Closing Reflections, Road Stories & Upcoming Dates (90:35–end)

• On Community & Growth:
  • Both reflect on what keeps them going: helping one another, “walking each other home” (Ram Dass quote), and the weird, rewarding family of comedy.
  • Annie plugs tour dates and her “Annie Wood” podcast, feeling she’s “in a groove right now where these are the best shows of my life…so fun. I feel very connected. It feels like such a vibe.” (91:44)

Memorable Quotes & Exchanges

• On Colonoscopies:
  “My rectum being stimulated by hot flowing water makes me smile. It feels good...I treat my asshole like it’s a war protestor in the 1960s. Hit it with the fucking hose, baby.” – Greg (05:00, 06:15)
• On Childhood Family Chaos:
  “My mom had like a psycho moment when I was a teenager where she would…press the gas [in the car] and she’s like, ‘why don’t I kill us all?’” – Annie (22:51)
• On Comedy Club Ego:
  “It’s like so embarrassing…you didn’t make yourself successful enough to be a household name for that person. Like it’s on me if someone doesn’t know who I am.” – Annie (23:53)
• On Community:
  “It’s like an infusion of joy. People with no cynicism...” – Greg (29:25)
• On Imposter Syndrome:
  “Success sometimes deepens self-doubt…she blew up, and then I got imposter syndrome.” – Annie (54:01)
• On Flakiness and ADHD:
  “I probably was being like…‘oh, I haven’t been around’, ‘cause I was just like, get it off of me. I was just kidding…No, I don’t feel that way.” – Annie (39:59)
• On Comedy Clubs & Ownership:
  “Suddenly they wanted, like, ownership of it or something…I bounced after that. Prefer less hands on my business.” – Greg & Annie (41:42–41:48)
• On Trauma and Healing:
  “I owe him, in a way, an apology because I asked for him to be incarnated on this earth to teach me these lessons, and I made him suck. I made him be a…child predator.” – Annie (68:22)
• On Walking Each Other Home:
  “You know the Ram Dass quote? We’re all just walking each other home…I mean, that makes me almost want to cry…” – Annie (71:27)
• On Awards & Progress:
  “Most improved is kind of a loaded award. Because it says that you used to suck.” – Greg (77:17)

Notable Moments with Timestamps

• 00:01–18:00: Greg’s colonoscopy and Home Depot story
• 19:51: Annie introduced; playful banter about style, Tourette’s, and nervous tics
• 23:36: Rage issues/generational trauma; “pop off” vs. grace moments
• 28:51–31:56: Tearful Best Buddies benefit memories
• 43:38: Annie’s kinkiest story—sex in the woods, plus crabs and twigs
• 48:45: Awkward group sex/threesome anecdotes
• 54:01: Aquafina story & imposter syndrome
• 74:09: Comedy Store feud with Donnell Rawlings; “pop-off” story
• 80:44: Annie’s teen trauma, family reckoning, powerful spiritual reframing

Podcast Tone & Closing

The conversation is raw, fast, and hilarious, but refuses to flinch from real pain. Annie and Greg joke about everything from being molested to inflaming headaches, but always with humanity and self-awareness. The episode is a must-listen for fans of honest, unfiltered comedy whose catharsis comes from laughter and truth-telling.

Annie Lederman Tour Dates & Podcast

Check Annie’s latest dates and catch her "Annie Wood" podcast for more unfiltered, unapologetic comedy.

For more, visit:

• fitzdog.com
• annielederman.com

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