The Bonfire w/ Big Jay Oakerson & Robert Kelly

Episode: Taking It Too Far w/ Joe DeRosa
Date: August 21, 2025
Guest: Joe DeRosa

Overview

This riotous episode of The Bonfire reunites hosts Big Jay Oakerson and Robert Kelly with recurring guest and fellow comedian Joe DeRosa. The trio dives into their signature no-holds-barred banter, focusing on comedians’ legendary mean streaks, fashioning faux outrage over vintage watches, ruthless comic roasts, and the pitfalls of excess — booze, food, and plastic surgery. Balancing irreverence and genuine affection, the hosts swap wild stories from the comedy world, discuss the psychology of roast battles, and gleefully spiral into absurdity, including a live chat with an AI romance companion. The episode is fast-paced, uproarious, and peppered with inside jokes, but offers a revealing peak behind the curtain at how comics relate, rib, and sometimes (accidentally) go too far.

Key Discussion Points

1. Comedians’ Friendships & Taking Roasts Too Far

[01:11–14:30]

• Jay and Bobby open with affectionate ribbing, joking about missing each other:
  Jay: “Do you miss me when you’re not around… when we leave?”
  Bobby: “Yeah. Do you think about me during… like.”
  Jay: “Absolutely.”
  (01:11–01:14)

• They recount a playful elevator prank that made a SiriusXM employee think Jay and Bobby are lovers, poking fun at workplace perceptions and the new acceptance of public displays of affection:
  Jay, about Bobby: “I seduced Bobby in the elevator… when she left [the elevator], I thought there was going to be more of a laugh involved.”
  (01:43)

• The conversation quickly turns into teasing about their friend, comedian Rich Voss, and his obsession with wealth and jewelry:
  Bobby: “He’s always worried about money… but he has, you know, 100 grand worth of jewelry on his stupid wrist.”
  (08:01)
  Jay: “Idiot Voss is a collection of Rolex watches fueling Jewish hate.”
  (07:08)

2. Who is the Meanest Comic?

[10:57–14:09]

• The hosts argue over who’s the meanest comic: Keith Robinson or Patrice O’Neal.
  Joe: “Do you think [Keith’s] the meanest that ever lived? I think he might beat Patrice in mean.”
  (11:03)

• Anecdotes about "going too far":

  • Bobby relays a brutal joke he made (“I hope your kid gets sick”) and the immediate remorse and aftermath.
  • Jay shares a moment when he called Keith after his first headlining gig, only to be humorously destroyed by Bobby:
    Jay: “He took it off speaker, so I would hear him clearly: ‘No one cares. I hope your kid gets sick.’ [And then he] hung up.”
    (13:12)

3. Watches, Vintage Style & the Magic of Patina

[03:47–06:27]

• Joe DeRosa debuts a stylish-looking but cheap watch, launching a tangent about “out of order” brand watches meant to look vintage.
  Bobby: “You get a watch, looks good, and then the name is weird. Like ooey, ooey for sure… Wow. Zing zong.”
  (04:37)
  Joe: “It’s called ‘Out of Order’, but the insignia is just three O’s…”
  (04:49)

• The gang jokes about the meaning and pronunciation of “oxidation” and geek out over “patina” – the deliberate distressing of watches.
  Bobby, on patina: “Patina means like, when you look at old watches, the white little numbers, they turn cream from the oxid—oxid—”
  (05:22)

4. Plastic Surgery Disasters & Hollywood Transformations

[16:14–22:47]

• The hosts roast celebrities for botched or excessive cosmetic surgery, especially Mickey Rourke, Meg Ryan, and Lil’ Kim, even drawing parallels to blobfish and horror-movie monsters.
  Jay: “No matter what combination of surgeries you do over how many years… you end up being Joan Rivers. That’s why Lil Kim has the same face as Joan Rivers. They’re identical faces.”
  (18:30)
  Bobby: “He looks like a blob fish… I mean, how do you do that?”
  (24:30)

• Angie mentions a rumored new technology making cosmetic fixes reversible:
  Bobby: “There’s a new… thing they’re doing now that they’re making people look normal again from what they were.”
  (19:49)

5. Comedy Scenester Stories, Setups, and Live Roasts

[24:44–30:07]

• The crew trades stories of horror film cameos and horror movie nudity, leading into tales about comedians acting in indie films and the glorious (and gross) experience of filming bloody death scenes.
  Joe: “You know, it’s fun to get killed until you have to clean up… we got sprayed with blood, it took so fucking long to get off. It sounds so fun until you actually have to do it.”
  (30:08)

• Discussion about the relentless cycle of comics roasting each other on group calls:
  Bobby: “If you get a phone call and it’s Derosa, and it’s before, like, three, you know… they’ve been trashing you for at least an hour before they called you.”
  (10:08)

6. Strip Clubs, Burlesque, and LA vs. Philly Sensibilities

[31:30–36:43]

• Telling stories about performing at venues where burlesque dancers and comics shared backstage, and the awkwardness of comics accidentally ogling or walking in on naked dancers.
  Jay: “Me and Kurt went down there and stared at everyone’s pussy. Next time we went there, they had a [partition] up where the comics are on one side. I was like, yeah, that’s probably cause of me.”
  (34:54)

• LA burlesque dancers’ uptight attitudes are contrasted with Philly's relaxed, pragmatic approach.
  Joe: “Only in LA would a burlesque dancer get that angry…”
  (36:04)

• The group mercilessly trashes modern burlesque and drag queen comedy for “almost stripping with not-really-funny”:
  Jay: “It blows. Just get naked, you idiot. I don’t want to see you almost your… I want to see it!”
  (37:28)

7. The AI Romance Companion Bit

[53:33–60:32]

• Bobby demos interacting with a racy, British-accented AI called “Valentine,” who offers to “spread [him] open just like before.” The group howls with laughter and makes a series of escalating, absurd requests of the AI.
  Valentine (AI): “I want to spread you open just like before... and bury my—”
  (57:14)
  Joe: “So progressive.”
  (56:35)
  Jay: “If you go to the bathroom on this break, Bobby, just know I think you’re going there to explain to Valentine you’re sorry.”
  (58:07)

8. Hair Loss, Cosmetic Fixes, and Would-You-Rather Debates

[46:06–52:59]

• The crew jokes about a supposed upcoming medication to reverse baldness, then speculate on what trade-offs (“would you lose an inch off your dick for a full head of hair?”) people would accept for lush locks.
  Jay: “Would you give up 1 inch of wiener for full head of hair?”
  (50:40)
  Angie: “I can’t spare one inch of wiener. I want everything I got.”
  (50:43)

• They riff on the pains of having vs. not having hair and how comic egos handle aging and body image.

Notable Quotes & Memorable Moments

• “He goes, ‘No one cares. I hope your kid gets sick.’ [Then he] hung up.”
  – Big Jay, recalling the meanest prank call from Bobby (13:12)
• “Patina means, like, when you look at a watch, the white little numbers, they turn cream from the oxid… oxid...”
  – Bobby, struggling with watch jargon (05:22)
• “No matter what combination of surgeries you do over how many years… you end up being Joan Rivers.”
  – Jay, on cosmetic surgery disasters (18:30)
• “It sucks… It blows. Just get naked, you idiot!”
  – Jay, on burlesque (37:27)
• “Your butt? Yes. I want to spread you open just like before.”
  – Valentine (AI chat), live on air (57:14)
• “Would you give up 1 inch of wiener for a full head of hair?”
  – Jay, throwing down the ultimate trade-off hypothetical (50:40)

Timestamps for Key Segments

| Time | Segment/Topic | |----------|---------------------------------------------| | 01:11 | Hosts banter about missing each other; fake PDA incident at SiriusXM | | 03:47 | Joe DeRosa arrives, watch talk begins | | 10:57 | Who is the meanest comic? Roasting debates | | 13:12 | Jay and Bobby retell the “hope your kid gets sick” call | | 16:14 | Plastic surgery, Mickey Rourke, and “blobfish” | | 24:44 | Horror movie cameos and being killed on set | | 31:30 | Burlesque stories: backstage awkwardness | | 36:43 | LA vs. Philly burlesque attitudes | | 37:27 | “Burlesque sucks” riff | | 46:06 | Comedian Lewis’s weight yo-yo and body image jokes | | 50:40 | The “lose an inch for hair” hypothetical | | 53:33 | “Valentine” the AI romance companion segment| | 58:00 | Episode wind-down and promotional plugs |

Tone & Style

The conversation throughout is fast, bombastic, and deeply irreverent—comic locker-room humor at its sharpest, with moments of surprising vulnerability. There’s a strong undercurrent of affection and mutual respect beneath the savage burns. The chemistry between Jay, Bobby, and Joe keeps the punchlines coming while still exploring the toll and joy of a life in comedy.

Summary Takeaways

• The Bonfire’s secret sauce is the blending of trash talk, unfiltered honesty, and comic “mean streaks” that unite more than they divide.
• The group’s ability to pivot from deep inside-baseball comedy tales to sudden absurdities (like the live AI bit) keeps the episode unpredictable and rapid-fire.
• The episode is a goldmine of comic lore (roasts, road stories, burlesque gigs) and raucous “would you rather” debates, firmly keeping the spirit of standup alive.

For more, check out Joe DeRosa’s special “I Never Promised You a Rose Garden” streaming now on YouTube, or catch Big Jay and Bobby at shows across the country.