The Bonfire w/ Big Jay Oakerson & Robert Kelly

Episode: Judgment Night with Jeremy Piven
Date: October 2, 2025

Episode Overview

This episode of The Bonfire, hosted by Big Jay Oakerson and Robert Kelly, features Emmy-winning actor and stand-up comedian Jeremy Piven as a special guest. The trio—true to the show's ethos—blend sharp comedy, industry stories, and personal confessions. They riff on Piven’s stand-up pivot, reflect on cult films and television, roast each other over past humiliations, and dig deep into the mechanics of stand-up, Hollywood, and the perils of crossing into new creative lanes. The tone is brash, fast, confessional, and full of signature Bonfire banter.

Key Discussion Points and Insights

1. The Legend of the Jeremy "Piven" Flyer

• [02:18–07:44]
  • The show starts with hilarious banter about "Piven" flyers—promotional materials Piven once left behind, some inadvertently edited to look like he's in blackface, which turned into an inside Bonfire game ("pivens" became rewards for guests).
  • Piven shares the awkwardness about physically handing out these flyers and how people's confusion often turns into genuine curiosity:

    "They want to punch you in the face, and then they look up and see it's me... Why are you doing this? And then it leads to a conversation." – Jeremy Piven [05:11]

  • The hosts detail how limited edition “pivens” became like bitcoin in their community—coveted and numerically tracked.

2. The Trials of Transitioning from Acting to Stand-Up

• [06:24–09:13]
  • Piven candidly discusses the difficulty of starting stand-up as a known actor, lacking the ability to "fail in the dark” and having to catch up on hard-won stagecraft:

    "I dare you to even name, beside Robin Williams, a prolific…" "No matter… Even though I've been on stage since I was eight, if you don't get those reps, you don't have a shot." – Jeremy Piven [21:17, 21:47]

  • He recounts bombing at clean charity gigs and being oblivious to the expected tone:

    "No one said do clean… My closing bit was… have you had so much cum squirted in your face... and everyone goes, literally a fucking room filled with people that have had their…" "It was beyond a disaster… The next day in the papers it was just like they were horrified." – Jeremy Piven [26:35]

3. Dancing with the Stars & Celebrity Reality TV

• [09:17–18:24]
  • The guys unpack the latest in Dancing with the Stars, riffing on Corey Feldman's elimination and low-effort celebrity dance moves.

    "All the other performers… first of all, are killing it for the most part. Andy Richter, who doesn't even dance… is still in the contest." – Big Jay Oakerson [12:59]

  • They act out what it would be like to be asked to join such a show:

    “Would you go on? Let's act it out... Yes!” – Robert Kelly [11:24]

  • Piven praises authenticity, regardless of skill:

    "The highest vibration in this life is authenticity… and that's his authentic self." – Jeremy Piven [14:28]

4. The Pain and Humor of Comic Gigs & Humiliation

• [18:24–38:41]
  • Kelly describes the pain of bombing at corporate gigs and the humiliation of dressing as Cupid for Cameo videos at his wife's suggestion:

    “My wife one year… You should dress up… as Cupid, and you can do it for your fans…” – Bobby Kelly [34:02]

  • The hosts mercilessly roast him, with Piven laughing at Kelly's $50 price for a full Cupid act:

    "What did you make for that particular cameo?" – Jeremy Piven [35:02] "Was it $50? $50 you got in a goddamn Cupid outfit." – Jeremy Piven [35:19]

5. Jeremy Piven’s Film and TV Retrospective

• [41:44–47:55]
  • Jay and Bobby catalog Piven’s cult filmography, especially films like PCU, Smoking Aces, and Judgment Night:

    "PCU was one of the first things I ever saw you in… I saw it 700 times as a kid and loved it." – Big Jay Oakerson [42:12] "Smoking Aces is up there with True Romance as far as cast..." – Bobby Kelly [42:58]

  • Piven reflects on movies’ rewatchability and notes how younger fans are rediscovering Entourage:

    "I got kids coming up to me, late teens, early 20s, screaming, 'Ari!'… during the pandemic, they’ve been binging it." – Jeremy Piven [45:18]

  • He shares backstories, like being mistaken for actually using drugs in Smoking Aces due to authentic acting.

6. Hollywood, Controversial Roles, and Method Acting

• [47:55–62:18]
  • They discuss the possibility of Entourage-style shows in today's world, the persistent draw of old-school storytelling, and working with controversial material.
  • Piven jokes about being a "grower, not a shower" during nude scenes [51:03], and recounts filming the infamous Very Bad Things with a porn star, not knowing her background.
  • Reflects on shooting Judgment Night in Chicago; confronts anti-Semitism on set (swastika on his mark), and discusses "method" acting gone wrong:

    "Everlast and these dudes… Bro, we were in character… That's not method, that's anti-Semitism." – Jeremy Piven [58:33]

  • Praise for Andrew Dice Clay both as a comic and actor.

7. Closing Out: Tour Announcements and More Roasting

• [63:34–End]
  • Jeremy plugs upcoming stand-up dates; Jay and Bobby shout their own dates and mock each other’s promotional tactics.
  • The hosts threaten more friendly humiliations and suggest explanations for any future Cupid sightings ("just say it was Jeff Ross" – Jeremy Piven [64:11]).

Notable Quotes & Memorable Moments

• On Confusing Flyers:
  "I looked down and I was in blackface on a flyer… so I apologize for being honest with whatever was going on with my face."
  – Jeremy Piven [02:44]

• On Standup:
  "If you don't get those reps, you don't have a shot."
  – Jeremy Piven [21:47]

• On Corporate/Charity Gigs:
  "I've said yes to performing… at my friend's stepfather’s memorial. They wanted a comedian… they all know each other and don't pay attention."
  – Big Jay Oakerson [30:05]

• On Movie Rewatchability:
  "People watched Old School 70 times… that doesn't happen anymore."
  – Big Jay Oakerson [42:39]

• On Younger Fans:
  "I'm going, bro, I got moisturizer on my face that’s older than you are."
  – Jeremy Piven [45:48]

• On Controversial Set Experiences:
  "It’s not method, that's anti-Semitism."
  – Jeremy Piven, referring to finding a swastika on his mark [58:33]

• On Humiliation for Low Pay:
  "Was it $50? You got in a goddamn Cupid outfit."
  – Jeremy Piven [35:19]

Timestamped Highlights

| Timestamp | Segment | |------------|---------------------------------------------------------------| | 02:18–07:44| Piven flyer origin story, “pivens” as Bonfire currency | | 09:17–18:24| Dancing with the Stars, Corey Feldman’s exit, TV schmoozing | | 21:17–26:35| Piven’s first stand-up gig, learning curve, and bombing stories| | 34:02–39:01| Bobby’s humiliating Cameo Cupid story | | 41:44–47:55| Filmography, cult classics, Entourage’s ongoing appeal | | 56:03–59:04| Judgment Night, filming in Chicago, encountering bigotry | | 62:18–End | Dice, method acting, tour plugs, final roasts |

Tone, Flow, and Takeaways

The episode is a rollicking, sometimes chaotic ride through Jeremy Piven’s recent comedy career, Hollywood anecdotes, and the unglamorous realities of the business. The hosts and their guest are brutally honest and endlessly self-deprecating, drawing big laughs from cringe-inducing moments—whether on stage, on set, or dressed as Cupid for $50. Through it all, the episode celebrates the highs, lows, awkwardness, and inside jokes that come with being in entertainment, from every angle.

For Fans and New Listeners:
This episode is a masterclass in comedic self-reflection, back-room stories, and how to keep pushing—and laughing—no matter where you start or end up in show business. Expect plenty of honesty, rapid-fire jokes, and the special chemistry only a couple of road-seasoned comedians and a game celebrity guest can deliver.