The Bonfire with Big Jay Oakerson & Robert Kelly

Episode: Button Fly Jeans & Heelys
Date: February 25, 2026
Theme: Blunt, hilarious takes on pop culture, money, nostalgia, comedy, and rollerblading, as Jay and Bobby riff on one-hit wonders, music royalty, locker room confessions, 70s/80s culture, career war stories, and misadventures on wheels.

Episode Overview

In this lively, wide-ranging episode, Big Jay Oakerson and Robert Kelly blend nostalgic storytelling and razor-sharp humor as they swap tales about music legends, old-school haircuts, and the perils of denim and rollerblades. The heart of the episode is their playful inquiry into rock-star money, embarrassing acting gigs, the mechanics of the "button fly flop," and their mutual inability to master trendy wheeled footwear. Crowning it all is Bobby's wild weekend gig—and the debacle with an irate audience member who tumbles down the club stairs, giving them comedy gold.

Key Discussion Points & Insights

1. One-Hit Wonders & Rock-Star Money

• Opening Riff (02:00): The duo debates if one-hit wonders actually cash in, dissecting whether backup band members ever get rich or if the publishing all goes to a single songwriter.

  • Jay: “What you’ll find out surprisingly about a band like this is they have a song that was in a commercial, and you’re like, oh, that was them.”
  • Bobby: “You know the bass player’s making Lugats.”

• Comparing Fortunes: They muse on if artists like the lead singer of Saliva or Survivor’s “Eye of the Tiger” guy are still rich, and whether smart, low-key rock stars like Richard Marx have retirement better handled than ostentatious icons like Ice-T and Vanilla Ice.

2. The Price (and Trauma) of Money

• Mariska Hargitay’s Legacy (06:00–12:00): The hosts ponder what it’s like to never have to worry about money, referencing Law & Order: SVU’s Mariska Hargitay inheriting both tragedy and wealth after her actress mother Jayne Mansfield’s infamous car accident.
  • Fascination with the “decapitation” urban legend:
  • Bobby: "Was I right? Was it because she was wearing a scarf and it got caught in the tire?”
  • DJ Lou: “Everyone says that, but it’s not true.”
  • Takeaway: Money can't erase trauma—“What would you rather have, that or never worry about money?” (10:25)
• Memorable quote:
  • Jay: “Have my mom.” (10:28)

3. Locker Room Confessions: Button Fly Jeans & The Flop

• Spiraling into a vividly comedic debate about 80s and 90s men’s fashion and anatomy (15:06–25:32):
  • Bobby waxes nostalgic on going commando in button fly jeans and the art of the “flop.”
  • Jay insists on anatomical realism and tries to chart “the path” of the penis in tight jeans, requesting Bobby’s assistance in mapping out the mechanics (“Can I draw the problem I’m seeing here?” 18:50).
  • Visual Comedy: Talk of launching a new Instagram for Jay’s "dick art" (19:03).
  • Quotable:
    • Jay: “A natural flop can only happen with a monster. Unless you prep your F position.” (22:39)
    • Bobby: “You don’t know the power of the dick.” (24:49)
    • Jay: “I know the power of denim.” (24:51)

4. Nostalgia for Hair & Fashion

• Epic 80’s Hairdos (30:29–33:24):
  • Bobby laments never achieving the “Kajagoogoo haircut” (the Too Shy singer’s iconic bangs-spike hybrid)—and tells of being cursed with cowlicks and curly hair after a fateful canoe masturbation session.
    • Jay: “You wanted a Kajagoogoo haircut?”
    • Bobby: “I wanted it. I couldn’t get it because of my…cowlick.”
  • They joke about leveraging AI to see “Kaja Goo Bobby.”

5. Roller Skating, Rollerblading & the Angst of Heelys

• 70s and 80s Childhood Recap (34:54–44:33):
  • Bobby recounts roller disco glory, his prowess on skates (“I could dance, I could go backwards”), and the perils of romantic pursuits on wheels at the Ballaroo and Malden rinks.
    • Bobby: “I lived a very gay life...smoking hot chicks would roller skate, dude. Oh my god.”
  • Jay admits: “All I can do now is embarrass myself.”
  • Christine and Jay bicker about her bruising post-rollerblading sessions; Christine insists she can skate, Jay remains skeptical.
  • The Heelys Dilemma (42:37): Can adult men get Heelys in size 14?
    • No luck—Heelys are “for women.”
  • Memorable soundbite:
    • Jay: “Roller skating and fighting on roller skates is the gayest thing in the world. Until somebody kicks somebody in the face with a roller skate.”

6. Comedy Club Adventures & Audience Mishaps

• Bobby’s Club Story (43:18–52:50):
  • Bobby regales the chaos from his show at “The Attic”—a club with an insanely steep staircase. After launching into a pro-Mexican bit, a drunken white audience member storms out (incensed by even hearing "Mexican"), promptly tumbling down the stairs.
    • Bobby: “Somebody falling downstairs is just a funny sound.”
    • Jay: “That means it’s back and ass, that’s the funniest... Someone hits their head, not funny anymore.”
    • Bobby: “It was just so funny to hear the sound. And then just to know it was somebody who didn’t like me made me so happy.” (49:56)
  • Their riffing on how clubs deal with “outrage” and the increasingly absurd expectations critics have of comics.

Memorable Quotes & Moments (with Timestamps)

• On one-hit wonders:
  • Jay: “You find out they got $3,000 apiece to make the song and like no points on the back end…someone else has their publishing.” (02:14)
• On old money and tragedy:
  • Jay: “I’m sure Mariska Hargitay went through some teenage fucking life sucks, my mom doesn’t pay attention to her.” (07:03)
• On the button fly and anatomical logistics:
  • Jay: “A natural flop can only happen with a monster. Unless you prep your F position.” (22:39)
  • Bobby: “When you’re with a girl, you fool it around... By the time you take it out, it just flops out and then it flops.” (17:37)
• On failed hair goals:
  • Bobby: “I just wanted that Kajagoogoo haircut, and I could never get it because…I had a cowlick.” (31:29)
• On their failed rollerblading aspirations:
  • Jay: “All I can do now is embarrass myself. I won’t learn it. I can’t learn how to roller skate now. I can’t.” (35:40)
  • Christine: “I can rollerblade. I can ice skate. I can ice skate. I can rollerblade.” (40:09)
• On roller skating fights:
  • Jay: “Roller skating and fighting on roller skates is the gayest thing in the world. Until somebody kicks somebody in the face with a roller skate; then it’s the most violent act you’ve ever seen.” (38:09)
• On club gigs and audience outrage:
  • Jay: “Those stairs are to go see comedy, or to throw yourself down if you’re trying to kill yourself and the demon just jumped into you really stuck.” (49:38)
  • Bobby: “It was a big limo pulled up with seven people…they all took a limo to the cool hipster place in the ghetto part of town.” (48:45)
  • Jay (on 'racist' complaints): “So the club, did they, like, sit you down and talk to you?” (50:21)

Notable Segments & Timestamps

• One-Hit Wonder Money & Publishing Rights – 01:48 to 04:53
• Mariska Hargitay/Old Money Tragedy – 05:48 to 12:00
• Button Fly Flop Debate – 15:06 to 25:32
• Haircut Nostalgia & KajaGoogoo – 30:29 to 33:24
• Roller Skates, Rollerblades & Heelys – 34:49 to 43:12
• Comedy Attic Story & Audience Outrage – 43:18 to 52:50

Tone & Style

• Blunt, Unfiltered, and Irreverent: The chemistry between Jay and Bobby shines through sardonic banter, self-deprecating confessions, and no-holds-barred asides on money, tragedy, and bodily functions.
• Nostalgic & Relatable: Many tales spring from their working-class upbringings, with affectionate ribbing over fashion and failed punk rock dreams.
• Comedic Philosophy: They expose the tightrope comics walk between irreverence and outrage, mining awkward moments and club mishaps for all they’re worth.

For First-Time Listeners

Expect a wild, hilarious ride—with tangents, old wounds, and camaraderie. You’ll get pop culture history, a crash course in blue-collar survival, and plenty of “did they really just say that?” moments, all riding shotgun on the nostalgia express.

[Listen to the full uncut episode on SiriusXM’s Faction Talk]