10-30-25 - Entertainment Drill - THU - w/Dale Hellestrae - Dorothy Will Not Be Seen In The Wicked Sequel

Summary

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Podcast Summary: Holmberg's Morning Sickness – Entertainment Drill with Dale Hellestrae

Date: October 30, 2025
Episode: 10-30-25 – Entertainment Drill – THU – w/Dale Hellestrae – Dorothy Will Not Be Seen In The Wicked Sequel
Host: John Holmberg with Brady Bogen, Bret Vesely, Dick Toledo, and guest Dale Hellestrae

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Episode Overview

Today’s episode centers around the “Entertainment Drill,” a rapid-fire discussion of quirky entertainment news and pop culture, with plenty of playful back-and-forth. Regular hosts John Holmberg, Brady Bogen, Bret Vesely, and Dick Toledo are joined by former NFL player Dale Hellestrae, who brings his trademark dry wit to the table. The team discusses everything from Arnold Schwarzenegger’s surprise billionaire status to odd Peloton classes, the new "Wicked" movie’s Dorothy problem, Toy Story 5 rumors, and general theater talk. As always, lighthearted tangents and jokes abound.

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Key Discussion Points & Insights

1. Celebrity Athleticism (01:51–02:30)

• John and Dale discuss Kevin Ray’s (Suns announcer) athletic ability.
  • Basketball: "He's pretty good at basketball. Yeah. He looked natural doing that." (A, 02:20)
  • Fighting/Golf: "Golf was the weirdest one. Fighting is pretty good. It's just awkward." (A, 02:06)
  • Banter about Al McCoy’s legendary “shazam” calls.

2. Arnold Schwarzenegger Joins the Billionaires Club (02:53–03:43)

• Arnold’s net worth is now $1.2 billion, thanks to smart investments with Dimensional Fund Advisors and stakes in real estate and hotels.
  • “Nice job, Arnold.” (A, 03:00)
  • "He also owns a piece of Easton Town Center in Columbus, Ohio... he's got some equity in Waldorf Astoria Hotel in Los Angeles." (E, 03:16–03:43)
  • Jokingly called “solid investor, actor, and politician.” (A, 03:43)

3. Spooky Season on Peloton (03:50–04:22)

• Halloween-themed “Friday the 13th” Peloton classes, where riders “pedal to survive” Jason Voorhees.
  • “There are three official Friday the 13th themed classes... users pedal to survive Jason Voorhees.” (E, 04:01)
  • “The instructors will be dressed up like camp counselors.” (E, 04:22)

4. “Wicked” Sequel Will Not Show Dorothy’s Face (04:28–06:05)

• Director Jon M. Chu has chosen never to show Dorothy’s face in the new film, to avoid stepping on audience perception.
  • “I don't want to step on who you think Dorothy is... The movie is still Elphaba and Glinda's journey.” (D, quoting Chu, 04:51)
• Playful confusion on how to pronounce “Elphaba.”
  • Dale tries: “Not E, L, P, H, A, B, A. Huh?” (D, 05:16)
  • “You didn't see Wicked.” “I did not see Wicked. Why?” (A & D, 06:03–06:05)

5. Theatre Experiences and Childhood Crushes (06:06–07:37)

• Dale admits he hasn’t seen “Wicked,” but has seen "Grease" and "42nd Street" in London.
• Light teasing about seeing “Grease” with British accents.
  • "Did Grease have accents? Were they British? … No, it was. It seemed like there's John Travolta." (A & D, 06:55–07:07)
• Childhood pop star crushes, including Bow Wow Wow’s singer, who “looks good for 58.”
  • “She looks pretty good for 58. Singer looks pretty good—I mean, for 58.” (A, 07:23–07:29)

6. Toy Story 5 – Cast Away Parody? (07:53–08:37)

• Tim Allen jokes about Toy Story 5 featuring a FedEx plane crash with 100 Buzz Lightyear dolls on an island (a la "Cast Away").
  • ”It’s Cast Away with Lightyear. That's hilarious.” (A, 08:07)
  • Allen would voice all the different Buzzes. "He does multiple voices of the Buzzes that are trapped on the island." (E, 08:14)
• Discussion quickly threads into franchise fatigue and the value of sequels.

7. Humorous Take on Movie Franchises & Streaming Confusion (08:32–09:47)

• Dale and John chuckle about horror franchises and redundant sequels.
  • "It's like Halloween 12. Come on. I see somebody get killed. It's scary... Why am I going to waste two hours?" (D, 08:39)
• Jabs about Dale’s difficulty using apps and moving money through technology.
  • “I can't get my money that he paid me through the Apple app.” (D, 09:30)
  • “You could probably counterfeit $33 faster than figure this out.” (A, 09:51)

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Notable Quotes & Memorable Moments

• On Arnold’s Success:
  “Solid investor and actor and politician. That's pretty good. Follow Arnold's advice.”
  – John Holmberg (03:43)

• On Avoiding Dorothy’s Face in ‘Wicked’:
  “I don't want to step on who you think Dorothy is... the movie is still Elphaba and Glinda’s journey.”
  – Dale Hellestrae quoting Jon M. Chu (Director) (04:51)

• On Pop Star Aging:
  “She looks pretty good for 58. Singer look pretty good—I mean, for 58.”
  – John Holmberg (07:23)

• Toy Story 5 Pitch:
  “It’s Cast Away with Lightyear. That's hilarious.”
  – John Holmberg (08:07)

• On Franchise Fatigue:
  “It's like Halloween 12. Come on. I see somebody get killed. It's scary... Why am I going to waste two hours?”
  – Dale Hellestrae (08:39)

• On Using Technology:
  “You could probably counterfeit $33 faster than figure this out.”
  – John Holmberg (09:51)

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Timestamps for Important Segments

• 00:00–01:12: Opening ads & show intro (skipped)
• 01:51–02:30: Kevin Ray’s sports skills
• 02:53–03:43: Arnold Schwarzenegger joins the billionaires club
• 03:50–04:22: Peloton’s horror-themed classes for Halloween
• 04:28–06:05: “Wicked” sequel to keep Dorothy’s face hidden
• 06:06–07:37: Theater stories, “Grease” in London, pop star crushes
• 07:53–08:37: Tim Allen’s Toy Story 5 “Cast Away” idea
• 08:32–09:47: Movie sequel fatigue, app/technology troubles

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Tone & Style

This episode is infused with the hosts’ characteristic sarcasm, camaraderie, and quick banter. The tone is fun, irreverent, and sometimes self-deprecating, with everyone willing to poke fun at themselves and each other. Dale Hellestrae’s inclusion brings a deadpan foil to John Holmberg’s rapid-fire hosting.

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Summary for New Listeners

If you missed this episode, you missed a lively, joke-filled riff on everything from celebrity fortunes to musical theater, horror movie cliches, and the hilarious complications of modern technology. The magic of HMS is in the effortless chemistry between host and guests, making even brief entertainment news a laugh-out-loud experience.

Transcript

[A]

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[A]

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[D]

Entertainment before he goes, has Kevin Ray been down there lately?

[A]

To the awkward reaction. Kevin's pretty good at basketball. He came by the house. He was not as awkward athletically strange.

[D]

As he is in golf. And fighting.

[A]

Golf was the weirdest one. Fighting is pretty good. It's just awkward.

[D]

Yeah, well that's probably good for him.

[A]

Yeah. Oh, sure.

[D]

Because if you don't know what's coming or what.

[A]

His angles are weird. He hit pretty hard, but it was really weird.

[D]

Basketball.

[A]

He's pretty good at basketball. Yeah. He looked natural doing that.

[D]

Yeah.

[A]

Surprised me, too. But he sees it so much. How could you not?

[D]

Oh, please.

[A]

I bet Al McCoy had a great job.

[D]

He had a great skyhook in your face.

[A]

He said that all the time. Shazam. And then he'd, you know, run back and do the you can't see me thing. That's what.

[D]

Yeah, you can't see me.

[A]

That's what he says. Is Brett your partner? Like. Yeah, Al. So you're getting used to getting in the bottom.

[D]

Watch this. You put it in the deep freeze.

[E]

Anyway.

[A]

Brady, please entertain.

[E]

Arnold Schwarzenegger's in the billionaires Boys club.

[A]

He's a billionaire now.

[E]

1.2 billion.

[A]

Nice job, Arnold.

[E]

He's in number 28. 81. Richest man in the world.

[A]

There are 2,000 billionaires and more.

[E]

Almost 3,000.

[A]

Oh, it's a 2,800.

[E]

Yeah.

[A]

Almost 3,000 billionaires.

[E]

His.

[A]

Damn it.

[E]

A big chunk of it is. He's in with fellow billionaire David Booth Dimensional Fund Advisors, which manages 12 billion in assets. He's got a piece of that. He also owns a piece of Easton Town center in Columbus, Ohio. That was the mall created by Les.

[A]

Wexner when they had all the lift weight weightlifting contests.

[B]

Right.

[E]

And he's got some equity in Waldorf Astoria Hotel. Astoria Hotel in Los Angeles.

[A]

Solid investor and actor and politician. That's pretty good. Follow Arnold's advice.

[E]

Peloton members get a special treat this Halloween. There are three official Friday the 13th themed classes currently available where the users pedal to survive. Jason Voorhees.

[A]

Oh, that's cool.

[E]

Camp Crystal lake. Yeah, they're 30 minute sessions where you're being chased by Jason.

[A]

I like that.

[E]

You get an exclusive shirt, too, with the Jason and the Peloton logo.

[A]

Okay. And Jason chases you, get a runaway. Oh, that's pretty good. Peloton is kind of a fun thing like that.

[E]

And the instructors will be dressed up like camp counselors.

[A]

Some of those instructors are hard to ignore.

[E]

Dale's got a huge story.

[A]

All right, go ahead.

[D]

There we go. Bless you, John.

[A]

Thank you very much.

[D]

Let's see here. Dorothy's face won't be shown in Wicked for good, even though Dorothy Gale, whoever the hell. That.

[A]

That's Dorothy from the wizard of Oz. Dale.

[D]

Dorothy Gale. She has the last name.

[A]

She had a last name. Yes. She's a fully rounded character.

[D]

Will be in Wicked for good. The audience will never, ever, ever get to see her face. Director John. John M. Chewy says, quote, I don't want to step on who you think Dorothy is. In whatever story that you came into this with, the movie is still Elphaba.

[A]

You're just making up words.

[D]

Not E, L, P, H, A, B, A. Huh?

[E]

Elphaba.

[D]

Elphaba.

[A]

What is the sentence you're making there?

[D]

The movie is still Elphaba and Glinda's journey.

[E]

Yeah.

[D]

And she is a pawn in the middle of all of it. Don't say. Yeah, you know how to pronounce.

[A]

It's a character's name. It's a name. It's got a capital E on it. I could assume when it has an and in another name, you would have fixed it. Oh, I almost went.

[D]

When you think of Dorothy, you probably picture Judy Garland, which is what I do.

[A]

Yeah, that's Dorothy Gale.

[E]

That's why he doesn't want to ruin that image.

[D]

It sounds like John doesn't want to change that at the cost of taking attention away from Glinda and El Faba.

[A]

All right, stop talking about Wicked.

[D]

El Faba.

[A]

You didn't see Wicked.

[D]

Ba, ba ba.

[E]

Elphaba.

[A]

You did not see.

[D]

I did not see Wicked. Why?

[E]

That surprises me.

[D]

It does?

[A]

Yeah. I thought you'd be there too. You don't like. You don't want to.

[D]

I'm not a big thief.

[E]

Too scary.

[A]

But you watch the wizard of Oz.

[D]

I did as a kid, but it's only because it's on in TV and get up and turn the channel.

[A]

You loved it. You sang.

[D]

I have seen a couple plays. So. I've seen Grease.

[A]

Okay.

[D]

See the newsboys in New York.

[A]

Oh, that's gay.

[D]

Saw a couple theater shows in London.

[A]

No kidding. What'd you see in London?

[D]

I think that's where I saw Greece.

[A]

Okay. You saw Greece in London?

[D]

Yeah.

[A]

Dumb.

[E]

I saw 42nd street in London.

[D]

They. They have the second something cheap tickets, whatever. Like the tickets that haven't been sold.

[A]

And did Greece have accents? Were they British?

[D]

No, it was. It seemed like there's John Travolta. Yeah, they were all. And what's her face.

[A]

That was a good one.

[D]

I had a Crush on a 10 year old.

[A]

No, it wasn't a crush. I just saw recently and thought, why didn't we as kids think she was hot?

[D]

Because the Mohawk.

[A]

Bow wow wow. And it was the Mohawk. But you look down, you're like, we should have thought she was hot.

[D]

And she's aged pretty well.

[A]

She looks pretty good for 58. Singer look pretty good. I mean, 458.

[D]

Yeah.

[A]

You throw that at the end because it's, you know, not go crazy. She looks Good.

[D]

Good for 58. Just leave it. And she looks good.

[A]

You can't. You can't. Because then people go, what? I'm like, for 58, like, oh, yeah. Well, for 58. That's how.

[D]

That's the only one.

[A]

Somebody. I respect his opinion on this.

[D]

Thank you. Oh, geez.

[A]

All right, close it up, Brady.

[E]

Tim Allen was interviewed about Toy Story 5, and he says, I hope one of the scenes make it. It's a FedEx plane that crashes. Crashes with a hundred Buzz dolls.

[A]

Oh, no.

[E]

Survive on the island. So it's kind of a spin off.

[A]

Oh, it's Cast Away with Lightyear. That's hilarious. Oh, that's a great idea. Do the pilots die?

[E]

And he does multiple voices of the.

[A]

Buzzes of the different Buzzes that are trapped on the island. That's a great idea. Oh, I like that a ton. You a Toy Story guy?

[D]

I like the first one or pretty good. Yeah. But come on. It gets very redundant, you know? I need to be entertained.

[A]

Yeah, you can't have that.

[D]

Yeah.

[A]

You need some depth.

[E]

I haven't seen four yet.

[D]

It's good.

[A]

It's not as good as the first three. First two are brilliant.

[D]

It's like Halloween 12. Come on. I see somebody get killed. It's scary. All right, whatever. Why am I going to waste two hours?

[A]

It's the kind of insight you get only on Thursdays with Dale sitting in.

[D]

The reason why your wife tunes in.

[A]

Really? Why everybody. Oh, I hadn't thought of that. About Halloween movies. Halloween 12. Somebody's gonna get killed and scary. That's it. We're done. Larry's coming up next. And then, of course, Fitz will be getting you all those code words starting again at 2:00'.

[E]

Clock.

[A]

And he will accomplish that by giving you the code word and, of course, giving you a chance at a thousand bucks. Just gotta take it in the app.

[D]

Dale, can I. Can I enter this? Sure I can.

[A]

Well, I'll say I do.

[D]

You do?

[A]

I will say you probably could enter it, but you're not going to be able to figure out how.

[D]

No. Okay. I can't find out.

[A]

Yeah. And there's no way. So download the KUPD app.

[D]

I can't get my money that he paid me through the Apple app he.

[A]

Had to give me.

[E]

How's that?

[A]

How did that work? He had to give me cash, and then I just paid you guys.

[D]

Yeah, but I have not been able to get the 33 he sent via Apple.

[A]

It's sitting in your phone. I know. He's done his part.

[D]

I have no idea how to get it.

[A]

You got to figure that out forever and ever. Way to do it. 33 bucks. Yeah, just. It's easy. Just Apple.

[D]

Everything's easy.

[A]

Brady will show you. It'll take five, seven days. Yeah. Yeah. You two figure it out. Dale, you two are like the US maybe next week. Yeah, you could probably counterfeit $33 faster and figure this out. Larry's next. You guys have a good one. We'll see you tomorrow on the morning Signal. Solo.

[E]

Hey, it's not weird.

[D]

It's pretty cool, actually.

[E]

No membership fee.

[A]

I have heard enough of this. It's John Holberg here from the morning sickness for lifechangerloan.com I had a friend text me the other day, and he was skeptical. He was like, there's got to be a catch, man. Math is absolute. It can't lie. So we went to the computer, put his info in the little [e-mail] and found out that his loan, which he owes $523,000 over the next 27 years on, could be paid off in eight years and he will save 389,000 in interest. That's insane. You should be skeptical. Ask questions. Then you'll see for yourself. It's not magic. It's just math. Lifechangerloan.com.

[C]

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[D]

Experience.