Fitzdog Radio – Episode 1117

Guest: Ryan Sickler
Date: November 20, 2025

Main Theme and Purpose

This episode features comedian and prolific podcaster Ryan Sickler, joining host Greg Fitzsimmons for a candid, uncensored, and hilarious conversation that covers everything from the evolution of comedy festivals and the shifting business of standup to deeply personal stories about family, health, adolescence, and sex. The episode is filled with hard laughs, confessions, and thoughtful asides as Sickler and Fitzsimmons share stories about careers, parenting, and some of their most formative (and embarrassing) life moments.

Key Discussion Points & Insights

Skank Fest Recap and Comedy Business Evolution

• Greg gives a lively rundown of this year’s Skank Fest in New Orleans, highlighting the wild antics, the impressive organization, and the unique “cancel culture” dynamic pervading today’s comedy scene.
  • “It's a festival...And now that model [of getting discovered for a sitcom] doesn't work. That just doesn't happen anymore. You get famous now by getting canceled.” (Greg, 07:17)
  • Notable stories include a bizarre late-night street encounter involving drugs, mistaken sexuality, and boundary-pushing festival events (08:20-09:45).
• Greg reflects on changing industry norms:
  • “You get famous now by getting canceled and then apologize on Tuesday, doing arenas by Christmas. I think that’s the new business model.” (Greg, 07:47)

Health, Family, and Midlife

• The pair discuss personal health journeys, genetics, and the impact of family history.
  • Ryan talks candidly about lifestyle changes after health scares (his brother’s bypass at 49), obsession with health metrics, and being in the “top 10% of healthy men for my age/height.”
    • “For my age and height, I am in the 10% of healthy men at my age, height, etc...That's bad for the country.” (Ryan & Greg, 11:16)
• Greg shares his own family’s tragic cardiac history and muses about finding the “best” way to die:
  • “My dad went down 53. Heart attack. His parents both died in their 40s.” (Greg, 12:44)
  • “If you’re gonna go, that doesn’t sound like a terrible way to go...going out at a great Italian restaurant.” (Ryan, 13:17)

Aging, Mortality, and Attitudes Toward Tomorrow

• An honest, funny exchange about approaching 60, ambitions declining, and existential views on aging.
  • Greg: “Who cares? Life is so overrated…Let me go, 68, I’m good with 68.” (Greg, 14:46)
  • Ryan’s attitude: “I want to see tomorrow for sure, yeah.” (Ryan, 16:04)
• They compare sleep habits, referencing Shohei Ohtani—deemed greatest baseball player—who sleeps 12 hours a night (16:07-16:09).

Sports Talk: Cal Ripken and Modern Legends

• Ryan and Greg nerd out on baseball, especially Cal Ripken’s legacy, streak records, and debate over whether staying too long helped or hurt the team.
  • Detailed statistics and context on Ripken’s streak (19:52).
  • The infamous Billy Ripken “f***face” baseball card story (22:24).
• Discussion also includes modern players (Shohei Ohtani, Yamamoto) and the flavor of today’s MLB.

Standup Comedy & Touring Life

• Both share stories about rarely missing shows, the mishaps that did interfere, and anxieties around flying, especially during the holidays and post-surgery.
  • “I spent 24 hours in Phoenix and never made it...devastated.” (Ryan, 24:24)
• Hilarious tangent about “miracle flights” with old people in wheelchairs (25:01).

Parenting, Cars, and Drift Racing

• Ryan shares pride (and some exasperation) over his son’s career as a master mechanic and drift racer, including the challenges of being a sponsor and the misadventures around car swaps and sponsorship logos.
  • “I sponsored his drift car...I gave money to—how much money?—too much.” (Ryan, 28:52)
• They unpack the culture of drift racing, father-son dynamics, and the challenge of balancing support and discipline.
  • “I’m not trying to be cool dad…I’m trying to be reasonable, be understanding...I was like, no dude, you got to go earn some of this.” (Ryan, 35:29, 36:04)

Adolescent Sexual Escapades & Homoerotic Friendships

• The episode turns into a laugh-filled confessional as both share stories about losing their virginity, adolescent experimentation, and the fine line between friendship and homoerotic play.
  • Greg’s legendary bus-masturbation story (53:05)
  • “We had a bet of who would lose their virginity first...And then after, like, six months, there was a couple times where I got close...” (Greg, 38:49)
• The “chicken heart” party joke and other adolescent antics become a big running theme.
• Discussion about their open-mindedness around sexuality and how those boundaries were understood or crossed as boys and teens, including pranks, bathing together, and skinny dipping.
  • “We had our silk shirts on. Our mascara’s running as we get out. That’s hilarious. You guys are getting out looking like you both just gagged on each other’s dicks.” (44:54)

Comedy Craft, Podcasting Advice, and ‘Worst Opener’ Stories

• Interviewing: Ryan shares insight for prospective podcasters:
  • “Number one technique is just to be a good listener...you gotta shut that off when somebody’s talking to you.” (Ryan, 64:05)
• Both talk about managing openers on the road and the etiquette of giving feedback (crowd work, material, grooming new comics).
  • “Your job as the feature act is to kill with 20 minutes of material…You should be showing the club owner that you can destroy for 20.” (Greg, 65:11)
• Ryan recalls being “promoted” by Damon Wayans and discusses how underrated Damon is as a comic (68:03).

The Changing Landscape of Comedy

• Greg and Ryan discuss “cancel culture,” audience sensitivity, the need for comedic risk, and how comedy scenes like LA, New York, Austin, and Chicago all serve a role.
  • “I feel like there’s a lot of audiences today, regardless of what the topic is, that are just like, can’t talk about that. Nope, nope, nope, nope.” (Ryan, 70:12)
  • “It’s not the topics that are the problem, it’s the execution.” (Greg, 69:49)

Ryan Sickler’s New Special: "Live and Alive"

• Announcing and plugging Ryan’s new YouTube standup special, which was filmed at Madison’s Comedy on State, sold out against tough local competition, and is a deliberate return to the vibe of classic club comedy.
  • “It’s just—it’s still only a couple weeks. It’s not even two weeks old yet.” (Ryan, 74:58)
  • “Why do we put a cap on? Like, it’s a forever thing. So I’m going to be promoting it forever.” (Ryan, 75:20)

Notable Quotes & Memorable Moments

• On the business of comedy now:
  • “You get famous now by getting canceled and then apologize on Tuesday, doing arenas by Christmas.” (Greg, 07:47)
• On health & genetics:
  • “For my age and height, I am in the 10% of healthy men at my age, height, etc...That's bad for the country.” (Ryan & Greg, 11:16)
• On dying peacefully:
  • “I want to die in my sleep behind the wheel of a car that’s speeding down the 405.” (Greg, 13:55)
• On opening for Damon Wayans:
  • “I got promoted to feature for the rest of the weekend because the feature was super low energy. Damon was like, I feel like I’m coming out to zero. Let Ryan’s energy [lead in].” (Ryan, 68:03)
• Podcasting advice:
  • “Number one technique is just to be a good listener...you gotta shut that off when somebody’s talking to you.” (Ryan, 64:05)
• On masturbation discovery:
  • “Discovering masturbation. I would put up there with the level of...electricity.” (Greg, 49:42)
• Most homoerotic moment:
  • “We had our silk shirts on. Our mascara’s running as we get out. That’s hilarious. You guys are getting out looking like you both just gagged on each other’s dicks.” (Ryan, 44:54)
• On discipline as a sponsor-parent:
  • “Here’s what I do know. The difference between working and non working. Your car can’t drive down the street right now. This guy’s out there doing donuts with my [logo] on one of the doors.” (Ryan, 34:57)
• On the fate of comedy specials:
  • “All these channels are like, well, you know, comedians are the essence of what we are, and we respect their art. No, you don’t. No. It’s all commerce.” (Greg, 74:24)

Timestamps for Key Segments

• Skank Fest Recap & Comedy Culture: 00:39–09:45
• Health Scares, Genetics, Death: 09:51–15:59
• Aging, Life Outlooks, Ohtani: 14:01–16:17
• Baseball Deep Dive (Cal Ripken, MLB): 16:18–23:33
• Tour Stories, Missing Shows, Airports: 23:37–26:48
• Parenting, Drift Racing with Son: 27:52–36:04
• Adolescent Sex, First Times, Masturbation: 36:33–54:03
• Confessional: Bus Masturbation, Massage Parlor Raid: 53:05–55:04
• Podcast Craft, Standup Road Etiquette: 63:03–68:12
• Damon Wayans & Comedy Evolution: 68:13–69:49
• Cancel Culture, Scene Divides: 70:12–72:05
• Ryan's Special "Live and Alive" Discussion: 72:16–74:58
• Sign Off, Mutual Praise, Final Laughs: 75:02–End

Tone and Language

The episode is unabashed, direct, and raunchy — true to both comedians’ storytelling style. They riff freely, share deeply personal and frequently explicit stories, and effortlessly balance sincerity with humor.

For New Listeners

This episode is a wide-ranging, combustive, and deeply funny deep-dive into both the state of comedy and the private lives of two veteran comics. Expect uncensored language, sexual anecdotes, life lessons, and real wisdom on health, parenthood, and the art of standup. If you like your comedy pods honest, raw, and heartfelt, this is a must-listen.

*“Thank you, dude.” (Ryan, 75:33)
*“Can we go shower together without chicken hearts? I’ll chicken heart you, bro.” (Ryan, 75:35)
“Should we get on a bus? You want to get on a bus with me?” (Greg, 75:48)