The Bonfire with Big Jay Oakerson & Robert Kelly

Episode: "Dancing Magicians" with Jim Florentine
Date: September 5, 2025 | SiriusXM Faction Talk

Overview

In this episode, Big Jay and Bobby welcome their longtime friend and fellow comedian Jim Florentine for a rollicking, inside-baseball discussion about the state of comedy, wild road stories, backstage tales from rock concerts, the evolving landscape of radio (with a focus on the rumored future of Howard Stern on SiriusXM), and the quirky world of "dancing magicians." The trio blends showbiz gossip, personal anecdotes, and their signature sharp humor to craft an episode full of laughs and surprising revelations.

Key Topics & Discussion Points

I. Howard Stern's Future & SiriusXM Drama

(02:19–12:58)

• Stern Contract Rumors: The crew discusses the intense speculation about Howard Stern potentially leaving SiriusXM, with Florentine offering predictions based on industry rumors and his personal experiences.
  • “He's my prediction, he's going to sign for like two years, a two year contract.” — Jim Florentine (04:41)
  • “The rumor is they're going to make him an offer he will refuse, but I guess he could also not refuse it.” — Bobby Kelly (04:56)
• Impact of Stern's possible departure:
  • The effect on staff, the network, and their own show’s positioning if Stern leaves.
    “Now that fucking... You told the Sterns leaving. The money's going to be rolling in.” — Big Jay (07:49) “We’re bump up. I think we're just going to take a little of that Stern cash.” — Bobby (07:57)
• Stern and the Podcast Boom:
  • Debating whether Stern would ever do a podcast, with consensus that he prefers the traditional radio format and loyalty to his long-standing staff.
    • “I don't think he’ll do a podcast. He wants to still take care of his staff... get a couple more years out of it.” — Jim Florentine (06:02)
• Showbiz Culture:
  • Reflections on how the radio and podcasting world has changed—pipelines to fame, old school versus new media, and the challenges of building or replacing an institution like Stern.
    • “There’s so much stuff coming out now, if he's going to do a show a week, it's going to fall completely through the cracks.” — Big Jay (05:38)

II. Howard Stern Show Anecdotes & the Comedy Circuit

(12:08–24:24)

• Behind-the-Scenes in Stern’s Studio:
  • Jim’s memories of wild in-studio moments: Jenna Jameson on the Sibian, Gary Busey wrestling with the staff, and what it was like for comics guest-hosting on Stern’s show. (12:44–13:41)
    • “I was there when Gary Busey… had a fight and they were rolling on the floor… I didn’t know if it was a joke or fake for the E Cameras.” — Jim Florentine (13:01)
• Comedy Road Stories:
  • Touring with Stern universe comics; the chaos of club and casino gigs; crowd expectations; how fame from Stern’s show would instantly sell out venues.
    • “He would plug a gig, 20 million people listen. Every show would sell out.” — Jim Florentine (17:42)
    • “The whole crew would go out and do the shittiest comedy shows ever.” — Bobby (17:53)
• Artie Lange’s Legendary Mayhem:
  • Hilarious and harrowing stories about performing and traveling with Artie Lange at the height of his substance abuse.
    • “By the time he's done with his set, he was fucking trash.” — Big Jay (15:35)
    • “To be bullied into drinking yourself sick is pretty hilarious. My audience go, boo. You're not going to drink 10 shots of Jagermeister?” — Bobby (16:25)
• Jay and Bobby’s Old-School War Stories:
  • Clashes between the Stern show and Opie & Anthony, Patrice O’Neal’s sensitivities, and the tribal nature of mid-2000s radio wars.
  • “You had to kinda pick a team... Patrice went over and did the show, but... it was just weird.” — Big Jay (21:05)

III. Radio Money, Staff, and Career Paths

(23:10–32:08)

• How the SiriusXM System Works:
  • Payouts, staff raises, and how success trickles (or doesn’t) down from stars like Stern to crew to supporting shows.
  • “Everyone got huge raises when they came over to Sirius from Krock… with his $500 million contract.” — Jim Florentine (23:19)
• Comedy Industry Truths:
  • Reflections on how fleeting opportunities can be, what “making it” means across eras, and the strange hierarchy of showbiz.
    • “It is funny, for Artie — that was his dream job, it's like you really didn't hang on to it.” — Bobby (13:45)

IV. Rosie O’Donnell "Price is Right" Segment

(24:46–27:46)

• How much to sleep with a celebrity?
  • A riotous, extended riff on what sum they’d need to sleep with Rosie O’Donnell, challenging each other to admit their "real" number.
    • “The real answer is $400. It's $0 or a million dollars. There’s no in between.” — Bobby (25:46)
    • “Yeah, I'd fuck Rosie O'Donnell for the story.” — Big Jay (26:09)
    • “But if it was Rosie, I would FaceTime you while I’m down eating her out.” — Big Jay (26:19)

V. The Comedy/Magic Club Circuit

(44:13–47:58)

• Dancing Magicians and Comedy Openers:
  • Tales of emceeing for local magician-comics with wild acts—flaming candles, animal tricks, questionable masks, and small-town crowds.
  • “He came out, he had a half mask face on, and he did around 10 minutes of dance at the beginning… and then a dove just shot out.” — Big Jay (44:47)
  • “Starting off in the black comedy club, when a white magician comedian would get on stage… the audience gave him the respect of a demon.” — Bobby (45:28)
• The World of Magic Collectors:
  • Discussion of magicians’ secret props and bizarre collections, like Danny Braff’s collection of famous false thumbs. (46:32)

VI. Music Industry Backstage and Rock Star Encounters

(51:06–59:16)

• Meeting Ozzy Osbourne and Metal Legends:
  • Florentine recounts getting to meet Ozzy after many previous encounters, seeing him in a wheelchair, and reflecting on the emotional weight of seeing aging rock stars.
    • “We’re saying goodbye to him; we're not going to see him again.” — Jim Florentine (51:28)
    • “When you met Ozzy, was it after or before [the show]?... There was a VIP thing, and they said Ozzy’s gonna come out.” — Big Jay (54:01)
• Visiting Rock History:
  • Sneaking into the location of the Black Sabbath album cover shoot with Jim Norton, having Ozzy post their picture, and the thrill for classic metal fans.
    • “We snuck in… Ozzy put it on his Instagram, so all the guys saw it.” — Jim Florentine (54:47)
• Legendary Tragedies & Tall Tales:
  • The infamous Randy Rhoads plane crash story is explored in depth, with rumors of sabotage and cocaine, as well as other music lore.
    • “The bus driver… thinks he crashed it on purpose.” — Jim Florentine (60:44)

VII. Prank Calls, Special Ed, and New Ventures

(32:28–40:29)

• Jim Florentine’s Return to Pranking:

  • Jim discusses bringing his iconic “Special Ed” character and prank call style back, using incoming telemarketer calls as material.
    • “These are incoming… telemarketers call you and you fuck with them?” — Big Jay (39:04)
    • “Yeah, one guy wanted to kill me… said he’d come over with a shotgun.” — Jim (39:10)
  • Hilarious fallout from one prank involving a fake home abortion, resulting in police breaking down his door.
    • “The lady believed it… my credit card company called the cops.” — Jim Florentine (39:30)

• Technology & Recording Antics:

  • Musings about the nostalgia and terror of old house phones, how recording prank calls has changed, and the horrifying memories of weird phone calls in haunted settings.
    • “Christine got some antiquey looking rotary telephone… the horror movie-like terror I would feel whenever it rang.” — Big Jay (40:54)

VIII. Memorable Quotes & Moments

• “To be bullied into drinking yourself sick is pretty hilarious.”
  — Bobby Kelly (16:25)
• “That was the thing. When Artie wants to leave, you leave. You just follow him. So I just followed him. And I left you in the dust.”
  — Jim Florentine (18:30)
• “Bus drivers are crazy. I mean, they're... their jobs nuts, dude.”
  — Big Jay Oakerson (64:01)
• “He would plug a gig, 20 million people listen. Every show would sell out.”
  — Jim Florentine (17:42)
• “Yeah, I'd fuck Rosie O'Donnell for the story.”
  — Big Jay Oakerson (26:09)

Notable Timestamps

• Howard Stern contract gossip: 02:19–06:56
• Howard’s legacy and show business changes: 10:41–12:58
• Being in Stern's studio during infamous moments: 12:44–13:41
• Artie Lange’s wild drinking stories: 14:12–15:59
• Opie & Anthony vs. Stern tribe wars: 21:05–21:33
• Rosie O’Donnell "what's your price?" game: 24:46–27:46
• Prank call revival and home phone gags: 39:04–41:42
• Magic acts and comedy emcee tales: 44:13–47:58
• Meeting Ozzy Osbourne and Sabbath nostalgia: 51:06–56:06

Tone

As always, the episode is loose, irreverent, and brutally honest. Friends for decades, Big Jay, Bobby, and Jim needle each other endlessly, moving easily from cynical showbiz analysis to crude, laugh-out-loud confessionals about their wild lives on the road and in the clubs.

For New Listeners

Expect sharp-tongued banter, unfiltered stories from both the stand-up and rock worlds, and a heavy dose of inside jokes. But beneath the roasting, there’s thoughtful reflection on careers, friendships, legacies, and the strange, often ridiculous ways fame and infamy are made.

Additional Links

• Jim Florentine Tour Dates & Special
• The Bonfire Show on SiriusXM Faction Talk, Channel 103
• Subscribe to The Bonfire Podcast

Whether you’re a diehard Stern-head, a comedy nerd, or just a fan of off-the-rails conversations, this episode spotlights everything wild, weird, and wonderful about life in the worlds of stand-up and radio.