Vault: Celebrity Incarceration Draft

Summary

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The Bert Show

Episode: Vault: Celebrity Incarceration Draft
Date: July 23, 2026

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Episode Overview

In this fun and irreverent episode, The Bert Show crew revives their long-running "Celebrity Incarceration Draft." The group takes turns predicting which celebrity will get arrested next, each drafting two picks to add to their rosters. The competitive spirit is high, with a growing jackpot for whoever predicts correctly, leading to plenty of laughs, playful jabs, and outlandish celebrity predictions. The show maintains its signature authentic, friendly, and banter-filled tone throughout.

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Key Discussion Points & Insights

1. Explaining the Celebrity Incarceration Draft (01:02–01:46)

• The concept: Each participant drafts celebrities they think are most likely to be arrested next. When a draft pick gets arrested, the person who picked them wins the jackpot.
• Rules:
  • Each person submits two picks per round.
  • Previously chosen celebrities remain on participants' rosters.
  • The pot grows with each round—about $200 already accumulated.
• Notable quote:

  "We try to predict which celebrity is going to get arrested next...We do about five bucks every time and we got a pretty good jackpot going right now." — Contestant 1 (01:04)

2. Recent Celebrity Arrests Kick Off This Round (01:58–02:18)

• Mentioned arrests:
  • Randy Quaid and his wife, for running out on a hotel bill.
  • Tito Ortiz (UFC fighter), for alleged assault.
• The draft is spurred by these recent high-profile arrests.

3. Draft Picks and Rosters Review (02:18–07:32)

• Players take turns recounting previous picks and choosing new ones.
  • Notable rosters include infamous personalities like R. Kelly, Lindsay Lohan, Mel Gibson, Andy Dick, and Snooki.
  • The group’s mix of picks ranges from the likely (serial troublemakers) to the under-the-radar (Brian Dunkleman).

Notable Draft Moments by Participant

Melissa’s Picks

• Past picks: R. Kelly, Tim Robbins, Brittany Murphy’s mother, Snooki, Tommy Lee, etc.
• New pick: Kiefer Sutherland

  "He just got, like, hammered in a fight a couple weeks ago, right? So I'm assuming a DUI's close at hand." — Contestant 3 (02:55)

Wendy’s Picks

• Adds David Hasselhoff because he’s “drinking the Hoff” and “not doing anything” post-America’s Got Talent.

  "We're going to add David Hasselhoff to that one because he's no longer a judge...he's not doing anything." — Contestant 4 (03:11)

Jen’s Picks

• Rounds out the Lohan family with Dina Lohan (Lindsay’s mother).
• Later adds Amy Winehouse.
• Notable quote:

  "I'm going to round out the Lohan family with Dina Lohan today." — Contestant 1 (03:45) "I am going to pick Amy Winehouse." — Contestant 1 (06:11)

Jeff’s Picks

• Adds Brian Dunkleman (original American Idol co-host), amusing the group with the randomness.

  "He's gonna get, like, a DUI in Boise." — Contestant 2 (04:19)

Bert’s Picks

• Chooses Blake Fielder-Civil (Amy Winehouse's ex-husband), jokingly renamed several times in a playful segment.
• Also picks Mickey Rourke for his "Boosh king" lifestyle.

  "If Boosh city was like a kingdom, this guy would be the king...any day he could get arrested. Mickey Rourke." — Host (05:32–05:45)

Other Entertaining Picks

• Robert Downey Jr. is reluctantly picked, with pushback due to his reformed image.
• Jeremy Piven is chosen for no specific reason, leading to a quick, deadpan exchange.
• Bobby Brown is picked because he's "back on the concert scene," and the group laments Whitney Houston's struggles.

4. Playful Banter & In-Jokes (Throughout)

• The gang riffs on unusual celebrity behaviors, the likelihood of various arrests, and the nature of celebrity "train wrecks."
• Several jokes about Amy Winehouse ("Blake Incarcerated"), and pop culture side notes about Whitney Houston and Mickey Rourke.
• They debate what would happen if two people’s picks were arrested together—how to settle a tie:

  "This is America, man. There are no ties." — Host (06:44)

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Notable Quotes & Moments (with Timestamps)

• "[The Draft Explanation]"
  "We try to predict which celebrity is going to get arrested next...We do about five bucks every time and we got a pretty good jackpot going right now." — Contestant 1 (01:04)

• "Kiefer Sutherland pick rationale:"
  "He just got, like, hammered in a fight a couple weeks ago, right? So I'm assuming a DUI's close at hand." — Contestant 3 (02:55)

• "On Mickey Rourke:"
  "If Boosh city was like a kingdom, this guy would be the king...any day he could get arrested. Mickey Rourke." — Host (05:32–05:45)

• "On Amy Winehouse and hypothetical joint arrests:"
  "What if they get arrested together and you guys have to split the money?" — Contestant 2 (06:23)
  "This is America, man. There are no ties." — Host (06:44)

• "On Whitney Houston's struggles:"
  "She cannot get through 'I Will Always Love You.' The voice is gone now, isn't it?" — Host & Contestant 1 (07:16–07:18)
  "She's a punching bag now...yeah, she's a punching bag." — Contestant 1 (07:28)

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Key Segments & Timestamps

• [01:02–01:46]: Introduction & Explanation of the Celebrity Incarceration Draft
• [01:58–02:18]: Announcement of Recent Celebrity Arrests
• [02:18–07:32]: Main Draft (Roster Reviews, Picks, and Banter)
• [05:32–05:56]: Comic Justification for Drafting Mickey Rourke
• [06:09–06:44]: Blake Fielder-Civil and Amy Winehouse Segment; Tie-Breaker Debate
• [07:05–07:32]: Bobby Brown pick and discussion about Whitney Houston's current state

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Summary

This episode of The Bert Show is a lively mock-sports draft with a comedic edge, built around celebrity downfall speculation. The hosts' camaraderie, pop culture acumen, and comic timing are front and center, illustrated by witty rationales for each controversial pick and the running jokes about celebrities’ notorious histories. Fans of celebrity gossip, friendly competition, and unfiltered podcast banter will find this episode especially entertaining.

Transcript

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[Host]

All right, Celebrity incarceration draft. Jim, what is this?

[Contestant 1]

Basically, this is where we try to predict which celebrity is going to get arrested next. So we each make our guesses every time a new celebrity is arrested and we put five bucks into the pot and then whoever actually correctly predict. Correctly predicts it will get that pot of money. We do about five bucks every time and we got a pretty good jackpot going right now, right?

[Advertiser]

Yeah.

[Contestant 2]

When we're done today, this will be our ninth round. So that's almost $200 that people win, right?

[Contestant 1]

Yes. So we get very competitive.

[Contestant 2]

Almost 250. Holy crap.

[Contestant 1]

Once we, once we have that celebrity on our roster, they stay with us. And so if anybody that we've picked, the entire round gets rested, then we get the money.

[Contestant 3]

Right.

[Host]

Okay, so this will be the order today.

[Contestant 1]

And we have to do two, right?

[Contestant 4]

Two.

[Host]

So we'll do it like the draft where we go. Whoever gets the first pick gets the last pick in the second round. So Melissa, Wendy, Jen, Jeff, and then Bert.

[Contestant 4]

Do we have the pics?

[Contestant 1]

The reason that we're doing two of them today? Randy Quaid and his wife were arrested yesterday after they turned themselves in in Santa Barbara, California. Remember, because they ran out on that big old hotel bill. And then the second celebrity arrested was Tito Ortiz. He's a UFC fighter and he was arrested for alleged assault against his girlfriend, former porn star Jenna Jamison.

[Host]

Alright, Melissa, you're up first. What were Melissa's former picks?

[Contestant 2]

Melissa, you have picked in the past. R. Kelly, Tim Robbins, Brittany Murphy's mama, Sammy sweetheart from Jersey Shore, Jeff Bridges, Charlie Sheen, Tommy Lee. And you're up.

[Host]

Solid roster.

[Contestant 3]

Yeah, I was trying to do a lot of political ones. All Right.

[Host]

Well, just one in the first round.

[Contestant 3]

Yes, just one. Jeff, when you're looking over the list, has Kiefer Sutherland been picked? Kiefer Sutherland.

[Host]

That's a good one is my guess. And he just caught, like, hammered in a fight a couple of weeks ago, right?

[Contestant 3]

Yeah. So I'm assuming a DUI's club close at hand.

[Host]

He's tea, don't he?

[Contestant 3]

Nice.

[Host]

Wendy is up next.

[Contestant 2]

Wendy, your picks are. Gary Busey, Danny DeVito, Courtney Love. Snooki. Mel Gibson, John Goslin, Misha Barton.

[Contestant 4]

And we're going to add David Hasselhoff to that one because he is no longer a judge on that America's Got Talent show and he's not doing anything. So.

[Contestant 3]

The Hoff.

[Contestant 1]

He's drinking the Hoff.

[Host]

Hasselhoff. Got it. Jen Hobby.

[Contestant 2]

Jen, your picks, thusly. Farley. Tila Tequila. Cat Williams. Damn it.

[Host]

Yeah, every time that one comes up, it just feels like a winner.

[Advertiser]

Yes.

[Contestant 2]

Lindsay Lohan. J. Wawawa. Michael Lohan. John Mayer. And Tara Reid.

[Contestant 1]

I'm going to round out the Lohan family with Dina Lohan today.

[Contestant 4]

Man,

[Contestant 1]

I need mama, daddy, and the most messed up daughter.

[Contestant 2]

My pick so far. Simon manjack. Who's Brittany Murphy's widow? Russell Brand. Eminem. The Situation. Spencer Pratt. Steven Seagal. Jamie Foxx. And I'm going to pick Brian Dunkleman.

[Contestant 4]

He's just mad at Ryan.

[Contestant 1]

Random.

[Contestant 5]

That would be one of those things

[Host]

that would come up, though. He'd be like, uncle Me got arrested.

[Contestant 2]

Yep. He's gonna get, like, a DUI in Boise. So who's left? Bert, your pick so far. Andy Dick. Jeremy Shockley, Steve O. Pauly D. Criss Angel, Jesse James. John Daly. And that's it.

[Contestant 5]

Blake Fielder. Civil. Amy Winehouse's husband, Blake, Incarcerated. Blake Incarcerated.

[Contestant 4]

That was a bloody good choice.

[Host]

She's been in the news again. Like, she tripped over her boobs the other day and, like, busted one up. Yeah, she busted one up. So they claim they're not drinking or doing as many drugs anymore, which still means they're doing a lot of drinking and drugs.

[Contestant 2]

What's his name?

[Host]

Not as many.

[Contestant 5]

Blake Fielder. Civil.

[Contestant 2]

He said it differently the first time.

[Contestant 5]

Blake Field. Da Civo.

[Contestant 2]

Is it Fielder civil or Civil Fielder Field?

[Contestant 5]

A Civo.

[Contestant 2]

Okay,

[Contestant 3]

you should be able to understand.

[Contestant 2]

I can understand.

[Host]

I also spit all over the mic.

[Contestant 1]

So here's your pick.

[Contestant 2]

The next pick is yours, Burt. You've already picked Blake Civil. Fielder. John Daly. This one's for Randy Quaid. Getting arrested with his crazy, smiling wife.

[Host]

Okay, I know this one. Is a little random. I just feel like he. If Boosh city was like a kingdom, this guy would be the king. And I feel like any day he could get arrested. Mickey Rourke.

[Contestant 4]

Oh, love.

[Host]

I just feel like, you know, he's kind of like 60 something years old, but he's just a boosh. And I think he's like. He goes out mostly with like 20 something year old women and he's out on the circuit drinking, so. Mickey Rourke.

[Contestant 2]

All right, who's next, me or Wendy?

[Host]

That would be Jeff.

[Contestant 2]

Robert Downey Jr.

[Host]

He's been clean for so long. Leave the dude alone. Leave Iron man alone, man.

[Contestant 2]

Wendy.

[Contestant 4]

I thought it was Jen.

[Host]

It's Jen.

[Contestant 2]

That's what I meant.

[Contestant 1]

Oh, me. I am going to pick Amy Winehouse.

[Contestant 3]

Oh.

[Contestant 2]

Oh, yeah.

[Contestant 4]

That's a good one.

[Contestant 1]

Touche. Blake. Incarcerated.

[Contestant 5]

I think Blake will get incarcerated first.

[Contestant 2]

Hey, what if they get arrested together and you guys have to split the money?

[Host]

We'll go right to the time. We'll have to go right to the

[Advertiser]

papers to see who got arrested first

[Contestant 2]

because they could.

[Contestant 1]

Well, no, Whoever got booked first, no,

[Contestant 2]

they could be arrested at the same time. I mean, sure, if they're both like stoned, hanging out in a park, doing

[Contestant 1]

each other, then we'd have to come up with a competition because Bert and I don't tie.

[Host]

This is America, man. There are no ties.

[Contestant 1]

There are no ties.

[Host]

This is not European.

[Contestant 2]

All right, Wendy.

[Contestant 4]

I'm going with Jeremy Piven. Just.

[McDonald's Promoter]

Good.

[Contestant 1]

Okay.

[Contestant 4]

No particular reason.

[Contestant 2]

Old school electric typewriter.

[Contestant 3]

I'm picking this guy because he is back out on the concert scene, believe it or not. Bobby Brown.

[Host]

Bobby Brown performing again.

[Contestant 3]

And it's a good choice. And his ex wife's not doing too well, and so I just. That's just a train wreck ready to happen.

[Contestant 1]

There's more videos of her today.

[Contestant 3]

Really? Poor thing.

[Contestant 1]

She cannot get through. I will always love you.

[Host]

The voice is gone now, isn't it?

[Contestant 1]

It's like. It's like gone. And I feel bad because we reported on it, what, like last week? And then there's even more videos out today. I'm like.

[Contestant 2]

And she can't not sing that song.

[Contestant 1]

She's a punching bag now. Yeah, she's a punching bag.

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