The Bonfire with Big Jay Oakerson & Robert Kelly
Episode: Pretty Woman Paco
Date: November 28, 2025
Episode Overview
This episode of The Bonfire with Big Jay Oakerson and Robert Kelly, titled “Pretty Woman Paco,” dives deeply into the comedians’ signature territory: hilarious, raw, and irreverent banter on pop culture, politics, celebrity gossip, and outrageous hypothetical scenarios. From 90s boy-band nostalgia to political absurdity and a full-tilt comedic pitch to transform their producer Paco into a “pretty woman,” this episode is a rollicking experiment in riff-based humor and fast-moving, boundary-pushing conversations.
Key Discussion Points & Insights
1. 90s Boy Band Nostalgia and R&B Cameos
[01:39–05:57]
- The show kicks off with a dissection of the trend in the late 90s and early 2000s of inserting token rap verses into pop and R&B songs—the “mid-song rap” that didn't necessarily have to be good.
- The hosts discuss memorable (and less memorable) appearances, like Nelly's guest spot with NSYNC and how certain members (Joey Fatone, Chris Kirkpatrick) faded into the background as Justin Timberlake's stardom took center stage.
- Visual gags about boy-band members and their dancing on different cars are peppered throughout, lampooning who drove what reflected their pop-status.
Memorable Quote:
“I love JT and them other white dudes. It was cool.” — Kumail Nanjiani (as a joke about Nelly's perspective, 04:05)
2. Red Pill, The Matrix, and Political Subtext
[06:32–08:40]
- The “red pill” metaphor spirals into a debate on whether knowing "the truth" is even desirable, referencing The Matrix and its offer of fantasy powers vs. harsh reality.
- Jay and Bobby humorously argue that if they were in the Matrix, they'd prefer blissful ignorance—”plug me back in and let me eat steak and dodge bullets!”
Notable Exchange:
“Why in God's name would you not choose that? Thank you, Morpheus, for teaching me how to conquer all of this.” — Kumail (07:21)
3. Matrix/Terminator Urban Legends
[08:40–09:59]
- They explore internet myths of an "old Black woman" (Sophia Stewart) allegedly being the original creator of stories that inspired The Matrix and The Terminator.
- Bobby admits his fondness for conspiracy rabbit holes and how easily he is convinced by these internet stories.
4. NYC Mayor Candidate: Rapper Past and Policy Proposals
[10:18–16:24]
- The hosts riff hard on “Zip Zap Zanzibar,” a fictionalized or exaggerated version of a real-life candidate—a “former rapper, socialist, and political aspirant with a rich mom.”
- They lampoon his campaign, focusing on his support for legalizing prostitution and his Bollywood-inspired rap videos.
Memorable Quote:
“He wants to make prostitution legal… it's not for me, it's for the younger generation, so they can enjoy themselves. Like Amsterdam.” — Bobby Lee (11:15)
- They joke about viral rap videos, the “scrubbing” of embarrassing digital pasts before campaigns, and the process of hand-picking candidates for image appeal over substance.
- Entertaining tangent on open-air markets, monkey assistants, and what makes a leader “fit” for NYC’s eccentric culture.
5. Movie Nostalgia: The Distinguished Gentleman & Eddie Murphy’s Career Arc
[17:09–22:36]
- Conversation spirals to The Distinguished Gentleman and Eddie Murphy’s trajectory from edgy comedy to family films.
- They debate which Eddie Murphy movies were actually good, comment on his scandal with a trans prostitute, and speculate about his romantic preferences.
Memorable Quote:
“Isn't that funny? Like the timing of that… whatever he did, because his excuse was so bad… ‘I just gave her a ride home.’” — Kumail (20:45)
6. Deep Dive: Eddie Murphy, Masculinity, and Trans Scandals
[21:04–32:09]
- Jay and Bobby analyze why Murphy would pick up a street-walking trans hooker ("He could call any escort he wants. He was looking for a low-key trans hooker pickup.").
- The discussion turns to their producer, Paco, and whether he could “pass” as a woman, including a comparison to the trans woman Murphy was involved with.
Memorable Exchange:
“If I was going down Hollywood Boulevard and I saw Paco dressed as a girl like that… you hit the jackpot.” — Bobby Lee (21:50)
7. The Pretty Woman Paco Hypothesis and Comedy Roast
[32:09–47:52]
- The show launches into its main recurring bit: offering Paco full sponsorship and support to become a trans woman—selecting breasts, imagining new comedy careers, and envisioning life on the road as Bobby’s opener and "camp follower."
- The details get comically specific: tit selection, contracts, what happens “post-op,” and rigid (but hilarious) rules for Paco’s hair, nipples, and butt aesthetics.
- Roleplaying ensues, including pickup lines, mock “car rides,” and establishing Paco as a “Polynesian princess.”
Memorable Quotes:
“You will be with Bobby on the road for five years straight. … But I do want a couple week notice and I do get to come inside you at least four more times before the five years is up.” — Bobby Lee (35:22)
“We do for Skankfest, prettiest girl guy… we get Paco, everybody gets one...” — Bobby Lee (42:21)
8. Social Media Addiction and “Serious” Statements
[48:06–52:54]
- The conversation turns introspective as Jay questions why comedians—even those whose brand is absurdity—feel compelled to make public statements about serious issues.
- Bobby attributes this to the dopamine rush of likes, retweets, and the addictiveness of social media affirmation.
Notable Reflection:
“It’s almost like a slot machine or a video game when you see those likes...” — Bobby Lee (52:45)
9. Comedy Habits, Snacks, and Behind-the-Scenes
[54:06–55:35]
- The cast rib each other about who is the loudest snacker during taping, culminating in the realization that everyone loves snacks, especially Christine.
Notable Quotes & Memorable Moments
-
On NSYNC’s Rise:
“They're only gonna pay him day rate... They're all dancing on cars where you can see where they are in the business through the car they're on.” — Kumail (03:30) -
On legalizing prostitution in NYC:
“...not for me, because I don’t want to do it... it's for the younger generation, so they can enjoy themselves. Like Amsterdam.” — Bobby Lee (11:15) -
On Eddie Murphy’s preferences:
“It’s funny—his wives have always looked very masculine. Sexy. Good looking, but masculine.” — Bobby Lee (29:24) -
On Paco’s transition offer:
“If you do this surgery, you will be with Bobby on the road for five years straight…” — Kumail (34:24)
“He's going to fall asleep and you're gonna kiss his neck. And, I mean, open his eyes. You're gonna be like, it's okay.” — Kumail (46:07) -
On social media validation:
“It’s almost like a slot machine or a video game when you see those likes.” — Bobby Lee (52:45)
Timestamps for Important Segments
- 01:39–05:57 – Boy-band/90s rap parody and breakdown
- 06:32–08:40 – Matrix/Red Pill humor
- 10:18–16:24 – NYC mayoral candidate’s rap career and legal prostitution pitch
- 17:09–22:36 – Eddie Murphy’s movie legacy & tabloid scandals
- 32:09–47:52 – Comic pitch for Paco’s transformation and ensuing zany scenarios
- 48:06–52:54 – Comedians reflect on social media, statements & likes
- 54:06–55:35 – Snack talk and studio atmosphere
Tone and Style
The episode is true to The Bonfire’s unfiltered, explicit, and free-associative style—playfully irreverent, packed with callbacks, in-jokes, physical descriptions, and a relentless focus on lampooning both pop culture and their own comedy-community foibles.
There’s a strong blend of raunchy hypothetical, meta-commentary about fame and “clout chasing,” and an impressive ability to take wild riffs to their (as Jay might put it) “logical, absurdist conclusion.”
Summary
If you appreciate honest, boundary-pushing, fast-paced comedy that isn’t afraid to say the unsayable or wander into the truly bizarre, Pretty Woman Paco is a showcase episode—hitting on themes of pop nostalgia, political parody, sexual taboos, and the comedy world’s own hilarious self-obsession. Whether you care about the real-life Eddie Murphy, social media dopamine, or boy-band deep cuts, there’s a joke and a roast in here for everyone.