Vault: All or Nothing Trivia on well endowed men Part 2

Summary

The Bert Show: Vault - All or Nothing Trivia on Well Endowed Men Part 2

Release Date: July 17, 2026
Hosts: Jen Hobby, Bert Show Cast
Special Format: Listener Call-In Trivia

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Episode Overview

This episode of The Bert Show brings back one of their most infamous and hilariously candid trivia segments: "All or Nothing Trivia on Well Endowed Men (Part 2)." The cast invites listeners to guess which five celebrity men—allegedly known for being exceptionally well endowed—appear on their secret list. The stakes are higher this round, with the addition of John Mayer concert tickets and a luxury spa massage package, leading to even more spirited and entertaining guesses from callers.

The core of the episode revolves around the “all or nothing” style trivia: to win, a caller must correctly name all five celebrities on the hosts' list in a single attempt, with the hosts only revealing how many correct names were guessed but not which ones. This structure builds suspense, teamwork among listeners, and plenty of cheeky, light-hearted banter.

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How "All or Nothing Trivia" Works

[01:23]

• Explanation by Trivia Explainer:
  • Five correct answers (guesses) are needed for a win; partial credit isn’t enough.
  • The host will tell callers only how many names they got right, not which names.
  • Success depends on listening to previous calls to spot patterns and eliminate wrong answers.
  • “...You'll start to see a pattern develop of which names become right... you have to listen carefully to everybody else's guesses...”
    — Trivia Explainer [01:26]

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Key Points & Memorable Moments

The Celebrity List — The Search Begins

[01:51]

• Premise by Jen Hobby:
  • “All these guys very confident. For good reason. You give us the five names of these guys.”
    — Jen Hobby [01:19]
  • The list is made up of living male celebrities rumored to be particularly well endowed.
  • Repeatedly, Jen and the team stress these are "alleged" and living figures, not from the past (excluding legends like Milton Berle).

Notable Listener Guesses and Results

• Mariela’s Guess (First Caller) [02:19]:

  • Russell Crowe, A-Rod, Colin Farrell, Gerard Butler, Hugh Hefner.
  • Result: None correct.
    • “None.” — Jen Hobby [02:32]
  • Commentary: “I thought those were all good guesses, too, man.” — Trivia Explainer [02:37]

• Rachel’s Guess [02:52]:

  • Tiger Woods, Justin Timberlake, Jamie Foxx, Johnny Depp, Brad Pitt.
  • Result: One correct.
    • “You got one, right?” — Jen Hobby [03:06]

• Giovanni’s Guess [03:20]:

  • Daniel Craig, Clive Owen, Zac Efron, Robert Pattinson, George Clooney.
  • Result: Zero correct.
    • “That's just your wish list.” — Trivia Explainer [03:33]
    • “There are zero on that list.” — Jen Hobby [03:36]

Raising the Stakes

[03:39]:

• Jen announces prizes now include John Mayer tickets and a one-hour massage at Intercontinental Buckhead.

• Julie’s Guess [03:58]:

  • Owen Wilson, Matthew McConaughey, Jamie Foxx, Reggie Bush, Ashton Kutcher.
  • Result: Two correct.
    • “You have two on the list.” — Jen Hobby [04:05]

• Sherry’s Guess [04:26]:

  • Aaron Donnelly, Liam Neeson, Mark Wahlberg, David Beckham, Milton Berle.
  • Result: Zero correct. Jen also recaps the “living” clue.
    • “Zero on that list.” — Jen Hobby [04:34]
    • “These are all dudes that are living... Milton Berle was on that list when he was alive.” — Jen Hobby & Trivia Explainer [04:36-04:44]

• Julie (Second Time) [04:53]:

  • Johnny Depp, Owen Wilson, Liam Neeson, Ashton Kutcher, Daniel Craig.
  • Result: One correct.
    • “You got one, right?” — Jen Hobby [05:04]

• Yale’s Guess [05:16]:

  • Ron Jeremy, Matthew McConaughey, Ashton Kutcher, Jamie Foxx, Sean Penn.
  • Result: Two correct.
    • “Okay, you didn't have four. You had two. But you did have two.” — Jen Hobby [05:41]

Highlights & Banter

• Jen Hobby and the Trivia Explainer maintain a playful tone throughout, gently ribbing contestants on their guesses.
• Frequent reminders that every wrong answer is “another piece of the puzzle.”
• Notable jokes about “wish lists” and the legendary status of Milton Berle.
• Engaged and spirited callers, some confidently believing they’re “sure of four” (Yale), but still missing the mark.

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Important Timestamps

• Explanation of Game Rules – [01:23]
• First Round of Calls and Guesses – [02:19] to [03:39]
• Announcement of Enhanced Prizes – [03:39]
• “Living Celebrities” Hint – [04:36]
• Final Caller Round for the Episode – [05:16]

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Notable Quotes

• “These five male celebrities obviously are the most well endowed in Hollywood.” – Jen Hobby [01:51]

• “I thought those were all good guesses, too, man.” – Trivia Explainer [02:37]

• “These are all dudes that are living... He's on, yeah, he's on like, the hall of fame list.” – Jen Hobby [04:36–04:44]

• “Okay, you didn't have four. You had two. But you did have two.” – Jen Hobby [05:41]

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Episode Tone & Dynamic

The episode is lighthearted, cheeky, and full of the camaraderie that makes The Bert Show a favorite for morning radio fans. The playful nature of the trivia, coupled with enthusiastic callers and snappy commentary from the hosts, keeps the tone upbeat and engaging. The segment walks the line between innocent fun and adult humor while remaining accessible for regular listeners and newcomers alike.

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Summary Conclusion

Listeners are left hanging as the secret list remains unguessed. The episode’s format encourages continued engagement, clever listening, and some careful deduction in the days to come. For fans of the show’s signature mix of irreverence, laughter, and audience participation, this episode is a prime example of The Bert Show at its best.

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For more of the fun or to jump into the guessing game, tune into The Bert Show’s Vault episodes daily.

Transcript

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[Trivia Explainer]

You have to get all the answers correct all at once. So basically, there are five answers to this question that that Bert is gonna pose to you. And you have to have five guesses. And in order to win the trivia, you have to get all five of them right. But if you listen over a period of time, then you'll start to see a pattern develop of which names become right. So because he's gonna tell you you got one right, you got two right, but not which ones. So you have to listen carefully to everybody else's guesses and make sure you call with five guesses.

[Jen Hobby]

All right? These five male celebrities obviously are the most well endowed in Hollywood.

[Trivia Explainer]

Allegedly.

[Jen Hobby]

Who are they? Give us five. We got one yesterday. So if you were listening, you should be starting with one.

[Trivia Explainer]

But we also had repeat guesses yesterday.

[Jen Hobby]

You gotta pay attention.

[Caller]

Okay?

[Jen Hobby]

Good morning, Q100. Who is this?

[Caller]

Hi, this is Mariela.

[Jen Hobby]

Hello, Mariela.

[Caller]

How are you?

[Jen Hobby]

Good. How are you this morning?

[Caller]

I'm just fine, thank you.

[Jen Hobby]

Okay, so we got five celebrities here.

[Caller]

Yes.

[Jen Hobby]

All these guys very confident. For good reason. You Give us the five names of these guys.

[Caller]

Russell Crowe.

[Jen Hobby]

I'm sorry.

[Caller]

Russell Crowe.

[Jen Hobby]

Okay.

[Caller]

A Rod. Colin Farrell, Gerard Butler. Hugh Hefner.

[Jen Hobby]

Okay. None.

[Kalshi Announcer]

None.

[Jen Hobby]

Okay.

[Kalshi Announcer]

All right.

[Trivia Explainer]

I thought those were all good guesses, too, man.

[Jen Hobby]

All right. Call back, though.

[Caller]

Okay.

[Jen Hobby]

Okay, remember, with every. With every incorrect guess, that's another piece of the puzzle.

[Trivia Explainer]

That's right.

[Jen Hobby]

Good morning to Rachel. You are on Q100.

[Caller]

Okay. I have Tiger Woods, Justin Timberlake, Jamie Foxx, Johnny Depp, and Brad Pitt.

[Jen Hobby]

Okay.

[Trivia Explainer]

You sound far too young to be guessing at this question.

[Jen Hobby]

Please don't tell us you're 15.

[Caller]

No, I'm not. I'm 20.

[Jen Hobby]

You got one, right?

[Caller]

Just one.

[Jen Hobby]

Just one.

[Caller]

Okay.

[Jen Hobby]

Okay. But if you were listening yesterday, we might have a. You know, you might have a match, right? All right. Good morning. You are on Q100.

[Kalshi Announcer]

Hello.

[Caller]

Hey, my name's Giovanni.

[Jen Hobby]

Giovanni. What's up?

[Caller]

Okay, my five guesses are Daniel Craig, Clive Owen, Zach Efron, Robert Pattinson, and George Clooney.

[Trivia Explainer]

That's just your wish list.

[Jen Hobby]

There are zero on that list.

[Caller]

Thank you, guys.

[Jen Hobby]

Okay. Thank you. I haven't even told you guys what we're playing for today. We've got the John Mayer tickets, and we also have. We're adding to the prizes today a one hour massage at the Intercontinental Buckhead.

[Caller]

Nice.

[Jen Hobby]

Okay, so stakes are raised a little bit here.

[Caller]

That'll be really nice.

[Jen Hobby]

Good morning to Julie. You were on Q100.

[Caller]

Hey, I've got Owen Wilson, Matthew McConaughey, Jamie Foxx, Reggie Bush, and Ashton Kutcher.

[Jen Hobby]

Okay. You have two on the list.

[Trivia Explainer]

Wow.

[Caller]

All right, thanks.

[Jen Hobby]

Okay, thank you. We're a little closer now. Sherry, good morning. You're on Q100. We're inching forward. This question is hard. Hey, Sherry.

[Caller]

Hello. Hi. I said Aaron Donnelly, Liam Neeson, Mark Wahlberg, David Beckham, and Milton Berle.

[Jen Hobby]

Okay. Zero on that list.

[Caller]

Okay.

[Jen Hobby]

All right. And we gave the hint yesterday. These are all dudes that are living. I mean, these are guys like, that are.

[Trivia Explainer]

Yeah, because I believe Milton Berle was

[Caller]

on that list when he was alive.

[Jen Hobby]

He's on. Yeah, he's on, like, the hall of Fame list.

[Trivia Explainer]

Yeah.

[Jen Hobby]

All right, so balance along. Julie, good Morning. You're on Q100.

[Caller]

Hey.

[Jen Hobby]

Hey.

[Caller]

Okay, can I guess now?

[Kalshi Announcer]

Sure.

[Caller]

All right, I got Johnny Depp, Owen Wilson, Liam Neeson, Ashton Kutcher, and Daniel Craig.

[Jen Hobby]

Okay, there's a big hint in this one. You got one, right?

[Caller]

One.

[Jen Hobby]

Yep.

[Caller]

Okay.

[Jen Hobby]

All right.

[John Daly]

Bye.

[Jen Hobby]

Bye. All right, we'll do one more today, and then we will move on Morning Q100.

[Caller]

Hey, good morning.

[Jen Hobby]

Good morning. Who's this?

[Caller]

This is yell.

[Jen Hobby]

Okay. Yale, you got five guys in Hollywood.

[Caller]

I know I've got four. It's my fifth one I'm unsure of.

[Jen Hobby]

You're sure of four of them?

[Caller]

I am. Okay, I got ron Jeremy, Matthew McConaughey, Ashton Kutcher, Jamie Foxx, and I'll go with Sean Penn.

[Jen Hobby]

Okay, give me those one more time.

[Caller]

Ron Jeremy, Matthew McConaughey, Ashton Kutcher, Jamie Foxx, and Sean Penny.

[Jen Hobby]

Okay, you didn't have four. You had two. But you did have two.

[Caller]

Okay. All right. Okay.

[Jen Hobby]

And that will help out a lot right there.

[Trivia Explainer]

Okay.

[John Daly]

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