08-15-25 - Entertainment Drill - FRI - w/Frank Caliendo And The Sklar Brothers

Summary

Podcast Summary: Holmberg’s Morning Sickness - Entertainment Drill (08-15-25)

Guests: Frank Caliendo & The Sklar Brothers
Date: August 15, 2025
Host(s): John Holmberg, Brady Bogen, Bret Vesely, Dick Toledo
Notable Guests: Frank Caliendo, The Sklar Brothers

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Main Theme

This episode of the Entertainment Drill is a comedic roundtable featuring John Holmberg, Frank Caliendo, and the Sklar Brothers. The conversation centers on humor, impressions, pop culture news, and playful mockery, with a focus on the absurdity of entertainment headlines and celebrity antics.

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Key Discussion Points & Insights

1. Guest Introductions & Banter

• The Sklar Brothers return for a second day in a row, joined by comedian and impressionist Frank Caliendo, who jokes about promoting the Sklars' show instead of his own.

  • Frank Caliendo: “I didn’t come to promote my shows … I came to promote the Sklar brothers show this weekend.” [01:31]
  • Sklar Brother: “You should be so lucky.” [01:45]

• Early jokes about being triplets, impressions of each other, and ventriloquist act nods further set in the irreverent and silly tone.

  • Frank Sklar: “Frank could do a great J impression. He can't do a good me at all.” [01:48]
  • Frank Caliendo: “When your mouth is moving, I’m looking at the other one and it’s throwing me off.” [01:56]
  • Sklar Brothers riff on Jeff Dunham and the puppet Peanut. [02:03-02:13]

2. Entertainment Drill - Mockery of Celebrity Headlines

• Matt Rife & ELF Cosmetics Controversy:
  • Comedian Matt Rife’s partnership with ELF Cosmetics backfired due to his prior controversial jokes.
    • Sklar Brother: “Good thing they researched that before.” [03:47]
    • John Holmberg: “Gotta make sure you’re not brand liability when you hire a comedian…” [03:50]
• Silly dig at celebrity endorsements and drag queen collaborations.

3. Absurd News and Running Gags

• Dora the Explorer Turns 25
  • The panel riff on the news that Dora turns 25, spiraling into surreal, adult-themed jokes about children’s characters “aging out.”
    • Frank Caliendo (deadpan): “She was going to be a bunny. This will attract you even more…” [04:23]
    • Sklar Brother: “Her career has taken a turn … Let’s be honest.” [04:32]
  • “Dora has to sell sex now because…” [04:34] and “It’s in the backpack.” [04:36] sparks more laughs.
  • Age jokes stretch to imagining Dora’s “75-year-old guts” [06:16–06:24], then get even more absurd with the suggestion of Dora appearing in a gritty Liam Neeson action film:
    • Sklar Brother (Liam Neeson impression):
      “I’m going to cut you open like a two-pound trout. Now Dora, I got a very special set of skills. I know exactly what I want. Your backpack has been taken.” [06:44]
• Extended Dora joke runs through 06:58–07:27, with darkly playful mockery of Nick Jr. characters and the dubious rhyme of ‘Dora’ and ‘Explorer’.

4. SZA Becomes Vans' Artistic Director

• The Sklars poke fun at SZA’s unexpected appointment as Vans’ artistic director.
  • Frank Sklar: “Who reps skateboarding more than SZA?” [05:21]
  • He riffs about asking SZA to “get rid of the guy who’s trying to sell weed to my kid at every skate park.” [05:54]
• Comedic take on the disconnect between corporate branding and actual culture.

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Notable Quotes & Memorable Moments

• On Matt Rife’s Endorsement Fail:
  “Good thing they researched that before.”
  — Sklar Brother [03:47]

• On Dora’s 25th Birthday:
  “Her career has taken a turn… Let’s be honest.”
  — Sklar Brother [04:32]
  “You gotta multiply times three... She’s got the body– you know, like the insides of a 75-year-old.”
  — Frank Sklar [06:16]

• Absurdist Liam Neeson/Dora Impression:
  “I’m going to cut you open like a two-pound trout. Now Dora, I got a very special set of skills... Your backpack has been taken.”
  — Sklar Brother as Liam Neeson [06:44–06:58]

• On SZA for Vans:
  “Who reps skateboarding more than SZA?... Also, see if you can get rid of the guy who’s trying to sell weed to my kid at every skate park.”
  — Frank Sklar [05:21, 05:54]

• On Rhyming Dora/Explorer:
  “Did you know that Dora and Explorer don’t rhyme? Not even close. That’s a hard R.”
  — Sklar Brother [07:35]

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Timestamps for Important Segments

• 01:30–02:13: Banter about being triplets & Jeff Dunham impressions.
• 03:10–03:53: Matt Rife & ELF Cosmetics controversy.
• 04:04–04:58: Dora the Explorer’s 25th birthday and career jokes.
• 05:21–06:16: SZA joins Vans; digression about skate culture.
• 06:44–07:18: Liam Neeson impression and further Dora jokes.
• 07:35–07:49: Observations on the non-rhyme of Dora/Explorer.

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Tone and Vibe

• Language: Sarcastic, playful, and sometimes a touch dark.
• Pacing: Fast, with comedic timing and strong interplay between guests.

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Wrap-Up

This episode is a whirlwind of pop culture mockery, character impressions, and irreverent humor. Whether riffing on Matt Rife’s PR troubles, Dora the Explorer’s imaginary adulthood, or SZA’s surprise appointment at Vans, Holmberg and his guests keep listeners laughing and a little off-balance. The playful, sometimes biting banter embodies the signature tone of “Holmberg’s Morning Sickness.”

Transcript

[Podcast Host]

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[John Holberg]

Hey, everybody, it's John Holberg here from the morning sickness and it's time once again for the pick of the litter brought to you by our friends at turf monsters a dot com. This week's pick the litter is a special little guy surrendered by his family because financial woes made it so they just could not give little manufacturer a great life. A little bit older. It's a bichon poodle mix. Smart as a whip. Check it all out. Lost our home.org or 98kupd.com it's the pick of the litter. Still streaming Bloomberg's Morning Sickness online at 98kupd.com we're about to start the circus. Steve O. Was just here. Frank Caliendo rolls in. He's promoting his own shows. And look who comes back. Day two. Second day in a row, the Sklar brothers have decided to roll right back in.

[Frank Sklar]

That's right. What's up?

[Frank Caliendo]

I'm explaining something to you though, John. I didn't come to promote my shows next week at the Desert Ridge Improv. I came to promote the Sklar brothers show this weekend.

[Frank Sklar]

You can at the Desert Ridge Improv. Beautiful room.

[Frank Caliendo]

A lot of people don't know I'm a triplet.

[Frank Sklar]

Yeah.

[John Holberg]

Yeah, that's right.

[Frank Sklar]

You should be so lucky.

[John Holberg]

Frank Sklar. Yeah, I like that you're the one.

[Frank Sklar]

That Frank could do a great J impression. Jason Impression in canning. He can't do a good me, but he can't do a good me at all.

[Sklar Brother 2]

At all.

[Frank Sklar]

It falls off.

[Frank Caliendo]

I just told them while we're off the air. I I1 your mouth is moving. I'm looking at the other one and it's throwing me off.

[John Holberg]

It's Jeff Dunham. It's Basically this.

[Frank Sklar]

Which one of us is Peanut? We're both Peanut. Get your hand off my Peanut.

[Sklar Brother 2]

What the hell?

[John Holberg]

It's a beautiful thing.

[Frank Sklar]

Wait, are you doing Peanut? I'm doing Walter. Walter. Hell the hell doing. I'm doing Dennis Rodman. Come on, man. Come on, man.

[John Holberg]

Listen, Dennis, we have the entertainment drill with Brady here. Say hi to Brady, everybody.

[Sklar Brother 2]

Brady, whatever.

[John Holberg]

Trying to ring me. Exactly. He's here.

[Frank Sklar]

Say hi to his second kidney.

[John Holberg]

That's right. Say hi to the one that's gonna stick.

[Frank Sklar]

Old lefty. He's six feet from the edge and.

[Sklar Brother 2]

He'S sinking his Creedney.

[Frank Sklar]

Yeah.

[John Holberg]

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[Guest Commentator]

Earlier this week, Elf cosmetics launched a new campaign with comedian Matt Rife.

[John Holberg]

Yeah, yeah.

[Frank Sklar]

It's all crowd work. They ask people how they feel. How do you feel? What type of blush do you like?

[Frank Caliendo]

He did.

[Guest Commentator]

He did a commercial with the drag queen Heidi and closet.

[Frank Sklar]

Oh, there you go.

[Guest Commentator]

It backfired because he people immediately the way the campaign is on the cosmetics. He did a joke in his special natural selection about domestic violence.

[Frank Sklar]

Oh.

[Guest Commentator]

So now the ladies.

[Sklar Brother 2]

Oh, yeah.

[John Holberg]

Because comedians are this guy. And very ser.

[Frank Sklar]

Good thing they researched that before.

[Sklar Brother 2]

Yeah, exactly. Yeah.

[John Holberg]

Got to make sure that you're not brand liability when you hire a comedian with Heidi. Heidi and closet as the two.

[Sklar Brother 2]

Yeah.

[John Holberg]

Because that's the stuff you need to sell your products.

[Guest Commentator]

Frank's got a huge store.

[John Holberg]

All right, go ahead, Frank.

[Frank Caliendo]

What?

[John Holberg]

Oh, this is my story.

[Sklar Brother 2]

Huh?

[Frank Caliendo]

I didn't know I was handed this. Oh, big deal here, guys. Explorers25. And she was originally gonna be what? Anybody know anybody?

[Frank Sklar]

What she's gonna explore.

[John Holberg]

She's 25.

[Frank Caliendo]

25.

[John Holberg]

It's been legal for seven years.

[Sklar Brother 2]

What I've been doing.

[Frank Sklar]

Change the haircut.

[John Holberg]

She was going to be.

[Frank Caliendo]

This will be attract you even more. She was going to be a bunny.

[Frank Sklar]

Her career has taken a turn.

[Sklar Brother 2]

Yeah.

[Frank Sklar]

Let's be honest.

[John Holberg]

Oh, she has to Sell. She has to sell sex now because.

[Frank Sklar]

It'S in the backpack.

[John Holberg]

What's she exploring today?

[Frank Sklar]

I started a WNBA game.

[Sklar Brother 2]

That's not in this.

[Frank Sklar]

That's not on the paper. I'm sorry.

[Sklar Brother 2]

It's do experiments are doing 25.

[Frank Caliendo]

I haven't even read this. It's perfect for brady debute of August 2000. There's something you may not have known the original. That's the topic that I just told you.

[Frank Sklar]

Yeah.

[Frank Caliendo]

Here's something that make that may come as a surprise. Dora. What?

[Sklar Brother 2]

What?

[Frank Caliendo]

What is this? This is the same thing. It's Reese's. The same thing, maybe. Oh, and. And she's a transgender.

[Frank Sklar]

They did not know that. She's hiding out of the closet.

[Frank Caliendo]

And that rife is in the backpack.

[Frank Sklar]

Hang on a min. That's right. I got one for you.

[John Holberg]

Go ahead.

[Frank Sklar]

Vans named SZA as their new artistic director because. Yes. Who reps skateboarding more than sza? She'll help create new collections and says, quote, my mission is to show that joy, community, creativity and fashion are all still intersectional. Yes. But here's my question for you. My son skateboarded and you know, I want to know. Talking directly to SZA right now, do you have a direct line to sza? Sza, if you're listening and I know you're a big fan of the show.

[John Holberg]

She's a huge fan. Please, like emailing in, right.

[Frank Sklar]

Design the vans, but also see if you can get rid of the guy who's trying to sell weed to my kid at every skate park. Can you do that? Can you get rid of that guy? Can you do that? That guy's everywhere. My kid's 12. I want to say the Dora the Explorer. Like she had. Like there is, you know, there's dog years and then there's dory years. So she's 25, but you got. I think you gotta multiply times three.

[John Holberg]

You think she's 75 years old.

[Frank Sklar]

She's got the body, you know, like the insides of a 75 year old.

[John Holberg]

What does that mean?

[Frank Sklar]

I don't know.

[Frank Caliendo]

I would have stopped earlier.

[Frank Sklar]

Goddamn 75 year old guts.

[John Holberg]

Yeah.

[Frank Caliendo]

You're not gonna be doing any AARP.

[Sklar Brother 2]

Ads in the future.

[Frank Caliendo]

This is the rife of a woman.

[Guest Commentator]

Maybe the other character, Swiper is now Wiper.

[Frank Sklar]

I wanna see insect.

[Sklar Brother 2]

Dora the Explorer.

[John Holberg]

I'm gonna gut her like a two pound shroud.

[Frank Sklar]

Liam Neeson.

[John Holberg]

We have Liam Neeson.

[Sklar Brother 2]

I'm going to cut you open like a two pound trout. Now, Dora, I got a very special set of skills. I know exactly who you are. I know exactly what I want. And I know what's in the backpack and it's mine now. Your backpack has been taken. I'm taking it back.

[John Holberg]

I would like to watch Liam Neeson like in a Roger Rabbit movie.

[Frank Sklar]

Just gut door of the explorer or just him going. He is doing more roles.

[Sklar Brother 2]

You never know. They opened her up to see what she's been eating. Like Jaws, a license plate and a boot. Dora, do you like movies with gladiators?

[Frank Sklar]

Oh, Dora. Oh, come on. Poor Dora.

[Sklar Brother 2]

Have you ever seen a girl?

[John Holberg]

Dora doesn't deserve this. She's a quarter century old for the privacy.

[Sklar Brother 2]

Hang around a gymnasium blossoming into womanhood and here we are treating her.

[Frank Sklar]

Let her be. Let her explore. Let her explore. Let her explore.

[Sklar Brother 2]

Did you know that Dora and explorer don't rhyme? Not even close. Where's. That's a hard R. They thought. That's a hard R. You don't like to use a hard R.

[Frank Sklar]

It's a hard R on rife too. Hard R. All right.

[John Holberg]

The Sklar brothers are here. The Guadalupe squares are upon us. And it's a very special version. Frank had come up with an idea.

[Sklar Brother 2]

Here.

[John Holberg]

You guys will be part of this, okay? But we think there's a theme we've developed here that may or may not win, but we'll try anyway. The Guadalupe squares are coming up. We need a girl, we need a guy. Call us up 585-9800 and we'll play him next. It's N Arizona's most powerful rock radio station. He said fully erect 98. It's John Holmerg here. Shannon away from my friends at New Vision Auto Glass. Brady just had his windshield replaced. Toledo just had his windshield replaced. And Brett evidently got jealous because his windshield got cracked on his drive to work the other day. New Vision Auto Glass, they're your best friends. They'll fix that ugly busted glass, then give you up to $375 back and you'll get dinner at the world famous Brazilian steakhouse Rodizio Grill. Go to new vis auto glass.com, see what you qualify for, then get it fixed. Call 480-210-9090. New Vision Auto Glass, proud sponsor of the Arizona Diamondback. It's John Holberg here from the morning sickness. And it's time to talk about TVs Doug Hopkins of my home group and Doug Hopkins.com I tell you about the house down the street from me that has had a for sale sign in the yard for Three months now. In fact, it's the fourth different sign they've got a new realtor all the time. I do know this, though. They wouldn't be dealing with all this stress if they'd have just called TVs Doug Hopkins. Because he's more than a guy buying your house. He makes an offer for your house, cash. As is, you don't have to do anything. The deal is over. So all you got to do is start the process online at Doug hopkins.com or sing Hopkins 1-800-sale now.

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