Vault: All or Nothing Trivia on well endowed men Part 3

Summary

Podcast Summary: The Bert Show

Episode: Vault: All or Nothing Trivia on Well-Endowed Men Part 3

Date: July 20, 2026

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Episode Overview

This episode features another round of The Bert Show’s popular "All or Nothing Trivia," centering on a cheeky and light-hearted topic: “Which living men in Hollywood are reputed to be the most well-endowed?” Listeners call in to guess the five names on a secret list, with the unique challenge being that the show only reveals how many answers are correct, not which ones. As always, the cast blends infectious humor and camaraderie with an energetic back-and-forth with their audience.

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Key Discussion Points and Insights

How the Game Works

• Explained by Jen Hobby (00:36):
  • Listeners must guess the five men believed to be the most well-endowed in Hollywood.
  • The list is newly curated and limited to living men.
  • Callers give five names; the hosts only state how many guesses are correct—never which ones.
  • The challenge lies in using partial feedback and deduction to win accumulating prizes.

Memorable Callers & Guesses

The Carpool Conundrum

• Two callers, apparently in the same car, call in with slightly different lists:
  • First List: Ron Jeremy, Ashton Kutcher, Eddie Murphy, David Letterman, Mikhail Baryshnikov (01:52)
    • Host’s feedback: “I believe you got one right.” (02:12)
    • Caller exclaims: “Got one. Oh, my God, you’re kidding me.” (Caller 3, 02:12)
  • Second List: Eddie Murphy, David Letterman, Ashton Kutcher, Ray J, Michael Jordan (03:12)
    • Host’s feedback: “You've got one right.” (03:33)
    • Host pokes fun: “Well, when we tell you guys we only have seven listeners, we’re not lying.” (Host, 03:49)
    • Co-host notes the callers’ lack of strategic guessing: “Not smart that you didn’t listen to what Bert said.” (Co-host, 03:52)

Progress and Smart Deduction

• Donna’s Guess: Leonardo DiCaprio, Ashton Kutcher, Jamie Foxx, Ewan McGregor, George Clooney (04:11)

  • Host’s feedback: "You got three right." (Host, 04:22)
  • Co-host is impressed: “That’s a good one right there.” (Co-host, 04:26)

• Preston’s Strategy: Jamie Foxx, Ashton Kutcher, Leonardo DiCaprio, Ellen DeGeneres, Toby Maguire (04:44)

  • Preston claims, “I got three of them. I know for sure... But the other two, I’m gonna, I’m gonna throw them out there.” (Caller 4, 04:41)
  • Host’s feedback: “You got three. Correct.” (05:06)
  • Hosts break down the logic: “If you’re like 90% sure that you have three right, you throw those three out. Then you give us two women. And if we tell you, you got three right, for sure. Got three. So that’s pretty smart thinking right there.” (Host, 05:19)

Prize Reminder and Roll-Over

• As no one gets all five, prizes continue to accumulate:
  • John Mayer concert tickets
  • Spa massage at the Intercontinental
  • $50 certificate to Fideaux
• Host teases, “We’ll add one more prize tomorrow morning to all or nothing trivia also. And we’ll do it at the same time.” (Host, 05:45)

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Notable Quotes & Memorable Moments

• “These are all living men in Hollywood, right? There’s been some debate about that...” (Game Explainer, 00:36)
• “Should have listened to the other person in the car.” (Host, 02:15)
• “That’s two large penises. We need three more.” (Co-host, 02:49)
• “Not smart that you didn’t listen to what Bert said.” (Co-host, 03:52)
• “You have to give us all five correct answers.” (Host, 04:36)
• “Technically, a woman can buy bigger than anybody on this list.” (Caller 2, 05:11)
• “Doing something very smart... That’s pretty smart thinking right there.” (Host, 05:19)

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Timestamps for Key Segments

• 00:36 – Game rules explained by Jen Hobby.
• 01:14-03:41 – Carpool confusion: two callers strategize (unsuccessfully).
• 04:08-04:27 – Donna makes a breakthrough with three correct names.
• 04:35-05:19 – Preston discusses deduction strategy and smart guessing.

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Tone & Vibe

The episode is playful, a bit risqué, and laced with camaraderie and fast-paced banter—typical of The Bert Show’s real-and-funny approach. Listeners are invited to laugh along with the crew and participate in this quirky piece of pop culture trivia.

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Summary Conclusion

Part 3 of "All or Nothing Trivia on Well-Endowed Men" showcases The Bert Show’s talent for blending audience participation, humor, and clever gameplay. While no listener takes home the jackpot this episode, a few get closer through sharper logic and deduction—making for an energetic and uproarious morning segment. With rolling prizes and playful teasing, the trivia fun continues, promising even more laughs and guesses next episode.

Transcript

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[Host]

All right, Jen, Hobby, explain what all or nothing trivia is and what we're focusing on right now.

[Game Explainer]

This is a very intriguing question about the men in Hollywood who are considered to be the most well endowed. This is a new list. And these are all living men in Hollywood, right? There's been some debate about that, but there's five answers to the question. But we're not going to tell you which ones you get right and which ones you get wrong. We're just going to tell you how many answers you've gotten right or how many you've gotten wrong. So you've got to listen. Over a period of time, a pattern develops and you can sort of, you know, eliminate some of the answers and keep around some of the answers. But you've got a call with five answers to this question. And once you get all of them right, that's why it's called all or nothing trivia, then you get all the prizes and we add a new prize every day.

[Host]

All right, here we go. And we will start with Alice.

[Caller 1]

Good morning, Michael Jordan.

[Host]

Oh, hold on, hold on. We're jumping right in. Okay, let's go.

[Co-host]

We're doing well, thank you for asking.

[Caller 1]

Go ahead, Michael Jordy.

[Caller 2]

Uh huh.

[Caller 1]

David Letterman.

[Caller 3]

Hello?

[Caller 2]

Yeah, go ahead.

[Caller 1]

Oh, hi.

[Caller 3]

Good morning, baby.

[Host]

What'd you think we were doing?

[Co-host]

Who are you talking to?

[Caller 3]

I'm sorry, you wouldn't believe this, but we've got two people in the car

[Caller 1]

that are online, so.

[Caller 3]

Or we're hanging on, so we're trying to win this today.

[Host]

Okay, so do you want the Michael Jordan and the David Letterman as part of your guesses or is that somebody else?

[Caller 3]

No, no, no, no. That's somebody else in the car. These are my five guesses. Okay, okay, okay, Sorry. Okay.

[Caller 1]

Ron Jeremy, Ashton Kutcher, Eddie Murphy, David Letterman and Mikhail Baryshnikov.

[Caller 2]

Because she's seen that poster, right?

[Host]

He's stuffed in that one. I believe you got one right?

[Caller 3]

Got one. Oh, my God, you're kidding me.

[Host]

Should have listened to the other person in the car.

[Game Explainer]

All right.

[Host]

One right. 404-741. Q100.

[Game Explainer]

They may be in the HOV lane.

[Host]

Oh, check this out.

[Game Explainer]

We're not winning this.

[Host]

All right, check this out. We just talked to Alice. Yeah, this is BB in the same

[Caller 2]

car

[Host]

on a different line.

[Caller 1]

We have the same list. We're going to edit this list a little bit. Okay.

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Okay.

[Caller 1]

All right, so we're going to go with Eddie Murphy, David Letterman.

[Co-host]

That's two large penises. We need three more.

[Caller 1]

Three more. Okay, so what about Ray J as one of them? Did you get. We got Michael Jordan. I don't know what he didn't get. You only got three numbers back.

[Host]

And what.

[Caller 2]

What she said. Never list back.

[Host]

I. I can't.

[Co-host]

Oh, they're passing the list around the car.

[Host]

I can't do that. You have to tell us.

[Caller 1]

Okay, okay, so the five that I want would be David Letterman, Eddie Murphy, Ashton Kishner, Ray J. And we said Michael Jordan. Give me one more. Michael Jordan.

[Host]

All right, did they say Michael Jordan twice on that list or no?

[Caller 2]

No, no.

[Host]

Okay, then you've got one right.

[Caller 1]

I got one right. Oh, my God. Okay, okay, whatever. You changed the list from before.

[Host]

No, we. You change carpool people.

[Caller 1]

Yeah, look, so we're, like, privileged to be two people in one car on the phone at the same time, right?

[Host]

Well, when we tell you guys we only have seven listeners, we're not lying.

[Caller 2]

But I will say. But I will say one thing they didn't realize is they made the same guesses when Bert said, you only got one right. And then the next person repeated two people. It's, like, not smart that you didn't listen to what Bert said.

[Host]

Good morning.

[Co-host]

Naughty.

[Host]

Donna, you're on T100.

[Caller 1]

Yes, Donna.

[Host]

All right, go for it.

[Caller 1]

Okay, my five guesses are Leonardo DiCaprio, Ashton Kutcher, Jamie Foxx, Ewan McGregor, and George Clooney.

[Host]

You got three right.

[Co-host]

That's a good one right there.

[Host]

We got three good ones.

[Co-host]

Nice.

[Host]

Go with one more today. This might be it. Good morning, Preston.

[Caller 4]

Good morning.

[Host]

All right, Preston, it is all or nothing trivia. You have to give us all five correct answers.

[Caller 4]

Okay, I got three of them. I know for sure.

[Host]

Let's do this thing.

[Caller 4]

But. But the other two, I'm gonna. I'm gonna throw them out there.

[Game Explainer]

Okay.

[Caller 1]

Okay.

[Caller 4]

The first three that I know I got for sure are Jamie Foxx, Ashton Kutcher, Leonardo DiCaprio. Those are my three that I know I got. But the other two would be Ellen DeGeneres and Toby Maguire.

[Host]

Okay, you got three. Correct.

[Caller 2]

Well, technically, a woman can buy.

[Game Explainer]

No, any size I know.

[Caller 2]

Can buy bigger than anybody on this list.

[Host]

You know what would have been a very wise move though? He was honest. Doing something very smart. If you're like 90% sure that you have three right, you throw those three out. Then you give us two women. And if we tell you, you got three right, for sure. Got three. So that's pretty smart thinking right there. Alright, so we continue tomorrow. You now got John Mayer tickets, Massage at Intercontinental Spa. I've got the $50 certificate to Fideaux. And then we'll add one more prize tomorrow morning to all or nothing Trivia also. And we'll do it at the same time.

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