The JTrain Podcast: "From Pessimism to Pushups" with Eddie Pepitone

Date: February 11, 2026
Host: Jared Freid
Guest: Eddie Pepitone

Episode Overview

On this "Chit Chat Wednesday," host Jared Freid sits down (virtually) with veteran comedian Eddie Pepitone for the first time. They cover a wide range of topics including pessimism in comedy, performing at challenging venues, the realities (and annoyances) of standup fandom, and why Eddie’s gym videos have unexpectedly inspired others. The conversation is candid, self-deprecating, and full of laughs, making it both honest and engaging for comedy fans and newcomers alike.

Key Discussion Points & Insights

1. Eddie Pepitone’s Comedy Roots & the “Expert in Pessimism” Label

• Jared introduces Eddie as an “expert in pessimism,” connecting his comedic persona to the tough Brooklyn upbringing described by Eddie.
• Eddie shares memories of growing up in 1960s Brooklyn, noting the contrast between that environment and the optimism he encountered upon moving to LA.
  • "We would get up every day and just yell, not another day, please, not another day." (01:36)

2. The Art of Self-Heckling: Vulnerability on Stage

• Jared recalls Eddie’s self-heckling bit, highlighting the depth and self-awareness in his comedy.
• Eddie explains the inspiration:
  • "I wonder what a heckler who knew me as well as I know myself would sound like...hey, Pepitone, how come you dream about red birds attacking your throat at night?" (04:24)
• They discuss the appeal (and personal challenge) of doing comedy that’s both absurd and deeply real.

3. Navigating Fan Expectations & Comedy Stereotypes

• Jared admits that some fans of Eddie’s pessimistic style can be a bit intense, sometimes missing comedy's broader possibilities.
• Eddie reflects on “healing through mirth,” adopting an exaggerated persona of the comic as a “mirth maker” for troubled times;
  • "I heal you people. I feel like I'm the mama bird and you the baby going, Eddie, our lives suck. Make us laugh." (06:45)
• They bond over the ways comedians are continually managing audience perceptions and their own need for acceptance.

4. Surviving Difficult Gigs: Edinburgh Fringe & Beyond

• Eddie recounts his bulletproofing experience at the Edinburgh Fringe:
  • "I feel like it totally made me bulletproof to fear...28 shows in 29 nights, an hour each." (10:01)
• They touch on the challenge of performing in front of very small (or uninterested) crowds and celebrate surviving such rites of passage.

5. “The Shouting Man”: Modulation and Feedback

• Modulation—varying one’s delivery—becomes a point of advice for both.
• Eddie discusses being labeled as “the shouting man” by critics and audiences:
  • “Describing me as the shouting man misses the point...Underneath the shoutiness for me is someone who's really thoughtful. The opposite of shouty. Right. Scared, insecure.” (18:00)
• Both agree that acknowledging performance techniques helps audiences feel cared for and signals professionalism.

6. The Pessimist’s Moment: Comedy for an Uncertain Age

• Eddie reflects on how our “collapse of society” is oddly well-suited to his comedy:
  • "Eddie Pepitone's time is here, and all it took was a collapse of society." (19:58)
• The pair joke about performing at upbeat locations (like Hawaii) where a dark, apocalyptic style doesn’t always land.

7. The Standup Boom: Social Media, Crowdwork Clips & Mediocrity

• Both discuss the explosion of standup content online, especially crowdwork clips that can overshadow more thoughtfully crafted comedy.
• Eddie bemoans seeing “mediocre” comics go viral:
  • "When mediocre people, in my opinion, get incredible popularity...I'm like, Jesus Christ. People are stupid." (26:25)
• Jared voices similar anxieties about finding one’s audience amid shifting comedic trends.

8. Shilling, Inspiration, and Staying in the Game

• They riff on comics (and even Steve Martin/John Hamm) doing ads, with Eddie drawing the line between “shilling” for necessity and excess.
  • "How about Steve Martin and Martin Short shilling for Wells Fargo? One of the worst corporations ever. They don't need money. That's my point." (28:17)
• Eddie’s gym videos become a symbol of accidental inspiration—intended as a goof, but genuinely motivating for people:
  • "I just did it as a goof at first...but it has inspired people because they're like, if this guy can get to the gym, then I can." (30:19)

9. Menu Games, Ice Hockey, and the Joys of Small Talk

• The hosts play a menu game, pretend-ordering from a healthy Florida cafe.
• Eddie shares plans to see the Winter Olympics in Milan and bonds over ice hockey fandom, with both reminiscing about the intensity and exclusivity of Boston sport culture.

Notable Quotes & Memorable Moments

• "We would get up every day and just yell, not another day, please, not another day."
  — Eddie Pepitone (01:36)
• "I feel like I heal people by exploring...I’m a mirth maker. I go from city to city in this broken nation, and I heal you people."
  — Eddie Pepitone (06:45)
• "I always tape the set...I'll be like, I just did 10 minutes and it was easy. I don't respect you people."
  — Eddie Pepitone (08:13)
• "To be really good live is the goal...I don't think there's any shortcut."
  — Eddie Pepitone (25:12)
• "When mediocre people...get popular...I'm like, Jesus Christ. People are stupid."
  — Eddie Pepitone (26:25)
• "I just did it as a goof at first...but it has inspired people because they're like, if this guy can get to the gym, then I can. And it's, like, been really nice."
  — Eddie Pepitone on his gym videos (30:19)
• "If there’s a historic storm coming, let me get in."
  — Eddie Pepitone (32:43)

Important Segment Timestamps

• Pessimism & Brooklyn Upbringing: 01:30 – 03:28
• Self-Heckling & Comedy Philosophy: 04:23 – 06:45
• The “Mirth Maker” Persona: 06:45 – 08:33
• Comedy Acceptance & Standup Anxieties: 09:13 – 11:06
• Edinburgh Fringe Festival Stories: 10:01 – 11:34
• Shoutiness, Modulation, and Feedback: 14:45 – 18:37
• Collapse of Society as Comedic Moment: 19:14 – 20:39
• Standup Boom & Social Media Critique: 25:04 – 27:28
• Gym Videos & Accidental Inspiration: 29:47 – 31:58
• Menu Game & Hockey Fan Chat: 33:02 – 36:41

Tone & Atmosphere

The conversation is candid, comedic, and full of mutual respect. Jared combines curious fandom with self-effacing humor; Eddie layers observational jokes with honest insight. The tone floats between light roasting, existential rumination, and warmth—making for engaging listening throughout.

Closing Notes

Where to find more:

• Eddie Pepitone’s special, “The Collapse,” is available on YouTube ([link in show notes]).
• Follow Eddie on Instagram: @eddiepepp
• Jared Freid: @jaredfreid

Final thought: This episode is a must-listen for anyone interested in the realities of standup, self-doubt versus validation, and the joy of finding comedy (and a bit of fitness!) in the face of it all.