12-05-25 - Entertainment Drill - FRI - w/Frank Caliendo - Frank Had Jon Gruden On Stage w/Him In Florida - Would Frank Do Masked Singer And Why He Turned Down Wife Swap

Summary

Podcast Summary: Holmberg’s Morning Sickness - Entertainment Drill - FRI - w/Frank Caliendo

Episode Date: December 5, 2025
Host: John Holmberg with Brady Bogen, Bret Vesely, Dick Toledo
Guest: Frank Caliendo
Main Theme:
A lively and comedic episode featuring Frank Caliendo, focusing on his on-stage experience with Jon Gruden, thoughts on reality TV offers like “The Masked Singer” and “Wife Swap,” and an entertaining group discussion about personal showbiz experiences, upcoming shows, and quirky holiday playlists.

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Episode Overview

This episode centers around beloved impressionist Frank Caliendo recounting recent gigs, particularly sharing the stage with Jon Gruden, while the hosts and Frank riff on sports, game shows, holiday traditions, and the absurdity of reality TV. Humor and relaxed banter drive the conversation, with a few memorable impersonations peppered throughout.

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Key Discussion Points & Insights

1. Frank Caliendo’s On-Stage Moment with Jon Gruden

Segment: 01:21-04:27

• Frank explains how Jon Gruden surprised him by joining his show in Tampa.
• Gruden, ever the football analyst, “takes over” the show with a mock play-by-play bit, asking Frank to impersonate whatever celebrity Gruden calls out.
• Frank and co-hosts riff on the hypothetical of taking the act on tour—“Dueling Gruden Pianos”—fueled by their shared affection for the bit.

Notable Quote:

“He kept telling me, he’s like, we should do something together. You think your fans would like it?” – Frank Caliendo, impersonating Jon Gruden (03:54)

2. Holiday Traditions, Globetrotter Memories, and Classic Sports Banter

Segment: 05:04-08:40

• Holmberg discusses New Year's Eve show plans with Frank at Tempe Improv, emphasizing early showtimes “so you can be in bed before all that nonsense.” (05:04)
• The group shares nostalgic stories about New Year’s traditions and attending Harlem Globetrotters events, blending in jokes about shrimp, cheese, and “baby people" food.
• Holmberg tells a hilarious story about being invited to play against a Globetrotters offshoot team, which led to a disastrous weighted ball shot and colliding with a dunker named “Skywalker.”

Notable Quote:

“Walking out there, Meadowlark Lemon legend is standing next to me before we all run out onto the court and he goes, ‘Hey man, grab this ball right here... just fire it up from 3 quarters. Can you hit that?’” – John Holmberg (07:11)

3. Entertainment Drill: Offbeat Holiday Playlists

Segment: 09:36-10:11

• Brady introduces a David Byrne-curated “holiday playlist for people who hate Christmas music.” Notable tracks include “Santa Claus Never Comes to the Ghetto” and “Santa Is a Gay Man.”
• The group offers sarcastic commentary on the irreverent song selections and imagined performances.

Notable Quote:

“Batman’s Coming. Something you don’t want to search.” – John Holmberg (09:54)

4. Reality TV Offers & Caliendo’s Reluctance

Segment: 10:23-12:01

• Discussion turns to “The Masked Singer," noting its return and upcoming Ozzy Osbourne tribute.
• Frank reveals he turned down “Celebrity Wife Swap” after finding out he would’ve been the “country bumpkin” family in an unflattering swap with a New York model—realizing reality TV is often a trap for embarrassment.
• There’s a running joke about the threat of losing “twice” on such a show: once by being portrayed as the loser, and again if your spouse prefers the swap.

Notable Quote:

“I was the loser family. And I was like, see, this is why you don’t do this.” – Frank Caliendo (11:40)

5. Upcoming Shows and Holmberg After Dark

Segment: 08:40-09:17, 12:07-12:29

• Frank plugs his New Year's Eve shows at Tempe Improv (6pm & 8:30pm), highlighting the appeal of early celebrations.
• Discussion of the “Holmberg After Dark” event, teasing special guests, including Jon Lovitz, and noting tickets are nearly sold out.

Notable Quote:

“The third annual Frank Caliendo. Morning sickness. Guest of the year. An award you’ve never, never gotten… It’s named after you, but you’ve never won.” – John Holmberg (09:08)

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Notable Quotes & Memorable Moments

• Frank, channeling Gruden:

  “I always wanted to do play by play, but I’m an analyst, so I’m gonna do play by play. And you’re gonna—Frank here, that’s you Frank, right—you’re gonna do other people I tell you to be.” (04:05)

• Holmberg, re: New Year’s shows:

  “6 and 8:30. So you can be in bed before... You don’t need all that nonsense.” (05:04)

• Brady, on holiday playlists:

  “Santa is a Gay man by Big Freedia.” (09:56)

• Frank, rejecting reality TV:

  “Listen, I already got my model.” (11:50)
  “The whole thing is Shrek.” (12:01)

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Timestamps for Important Segments

| Time | Segment Topic | |-----------|------------------------------------------------------| | 01:21 | Frank’s on-stage moment with Jon Gruden | | 03:54 | Gruden encourages Frank: "We should do something…" | | 04:33 | Dueling Gruden Pianos & comedic tangent | | 05:04 | New Year's Eve at Tempe Improv details | | 07:11 | Holmberg’s Harlem Globetrotter story | | 09:36 | David Byrne’s anti-Christmas playlist | | 10:54 | Masked Singer discussion; Ozzy tribute | | 11:21 | Frank explains turning down Celebrity Wife Swap | | 12:07 | Final plugs for upcoming live events |

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Tone & Style

The episode is quick-witted, irreverent, and playful, characteristic of “Holmberg’s Morning Sickness.” The humor is layered—a blend of sports nostalgia, self-deprecation, and the group’s trademark skewering of pop culture and themselves. Frank’s impressions and willingness to send up both himself and the premises of TV and stage are central to the appeal.

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Summary:
If you missed this episode, you’ll hear Frank Caliendo at his off-the-cuff best, swapping stories, zingers, and show-business insight with Holmberg’s crew. From the surrealism of improv with Jon Gruden to the calculated avoidance of reality TV humiliation, the banter is rapid, funny, and full of quotable moments. If you love sports, comedy, or just want a genuine laugh about modern showbiz, this episode delivers.

Transcript

[Frank Caliendo]

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[John Holmberg]

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[Dick Toledo]

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[Dick Toledo]

You thought that was funny?

[John Holmberg]

You were laughing like a hyena when he said it. What the hell is wrong with you?

There you go. Coming out to play. Frank Caliendo joining us today to come out to play. We're talking off the air about John. You were on stage with Jon Gruden. He came up with you in Tampa.

[Frank Caliendo]

Popped in there, man, up in Tampa. Showed up. Did a little Tampa too. I'll tell you what, man. Losing Tampa two step we did we put on tap dancing shoes. You ever wear those, John? Yeah, John Holberg.

[John Holmberg]

That's right.

[Guest/Co-host (possibly a sports personality)]

Yeah.

[Frank Caliendo]

I tell you what, man. T for two and two for tea. Let's go.

[John Holmberg]

You guys.

[Frank Caliendo]

Hold on, I'm tapping.

[John Holmberg]

Did you have him in the crowd? Oh, he's tapping. I'm sorry.

[Frank Caliendo]

You got a. You got a button over there. Over there that does tap dancing.

[John Holmberg]

Let me check.

[Frank Caliendo]

You got that door open and close.

[Brady from HMS]

Shuffle off to Buffalo.

[John Holmberg]

Nothing. I got that.

[Frank Caliendo]

Shuffalo. You ever put two words together, they call out a mashup, man.

[John Holmberg]

It's Mark Shuffalo.

So was he in the Crowd for your show.

[Frank Caliendo]

I'm trying to do it. I'm shuffling every. I'm shuffling Mark Shuffalo.

[John Holmberg]

He's got a dancing show. The Mark Ruffalo Shuffle. And the Super Bowl Shuffle just.

[Guest/Co-host (possibly a sports personality)]

It came out 25 years ago, 40 years ago.

[Frank Caliendo]

And then if you're looking at the fridge and I'm a rookie I may be large but I'm no dumb cookie See me hit you, see me run.

[John Holmberg]

We've got a documentary coming about the Super Bowl Shuffle. Maybe it's time Frank got the makeup on.

[Frank Caliendo]

I'll tell you what.

[John Holmberg]

Did all of his people doing that Super Bowl Shuffle, that'd be the beginning.

[Frank Caliendo]

And end of everything right there, man.

[John Holmberg]

Yeah. That's the full circle. And then you just drop the mic.

[Frank Caliendo]

Gary Fencik, Hitman. Yeah, they call me Hitman. Don't know what they mean. I tell you what they mean. That's back when football is real. You used to get the hit, guys. Steve Fuller, backup quarterback, was Gruden in your audience?

[John Holmberg]

And then you're like. So he watched the whole show. And then you said, come here.

[Guest/Co-host (possibly a sports personality)]

Yeah, I said, some people, they had to know he was there.

[John Holmberg]

Yeah, but.

[Guest/Co-host (possibly a sports personality)]

Well, he was there. Tim Legler was there at that show.

[Frank Caliendo]

Wow.

[Guest/Co-host (possibly a sports personality)]

It was pretty. It was cool show. Jim McElvaine, seven foot one. Jim McIlvaine was there.

[John Holmberg]

Yes. This is all in Tampa. Yeah, they're just hanging out.

[Guest/Co-host (possibly a sports personality)]

Anderson, the guy who beat. He was with Fairleigh Dickinson University that beat.

Purdue when they were the number one seed.

[John Holmberg]

Remember that at all? Oh, and basketball.

[Guest/Co-host (possibly a sports personality)]

That's right. Tournament.

[Frank Caliendo]

Yeah.

[Guest/Co-host (possibly a sports personality)]

So it was a lot of.

[Brady from HMS]

That's.

[Guest/Co-host (possibly a sports personality)]

I mean, I invited all of them, and sure, the only four that showed.

[John Holmberg]

There's a lot of people that are always open invitation, but those guys show, and then you call Gruden up on.

[Guest/Co-host (possibly a sports personality)]

Stage, he go, yeah, He. He kept telling me, he's like, we.

[Frank Caliendo]

Should do something together. You think your fans would like if we did something together? I think they would. I'm like, I'll tell you what, man. I think they would.

[Guest/Co-host (possibly a sports personality)]

And he got up there and had me do. He kind of takes over.

[Frank Caliendo]

He's like, I always wanted to do play by play, but I'm an analyst, so I'm gonna do play by play. And you're gonna. Frank here. That's you, Frank. Right. He's gonna do other people that I tell him to be.

[Guest/Co-host (possibly a sports personality)]

So we did it like that.

[John Holmberg]

And he worked you through it. Yeah, yeah. Was it.

[Guest/Co-host (possibly a sports personality)]

And he wants to do, like, stage shows like that.

[John Holmberg]

He wants travel let's go on the road, Frank. Take it on the road.

[Frank Caliendo]

Just be pretty good.

[John Holmberg]

If Adam Ray can make a year and a half out of Dr. Phil, you and Jon Gruden can fill a couple of places.

[Frank Caliendo]

The Dueling Gruden Pianos.

[John Holmberg]

For no reason.

[Frank Caliendo]

We got two pianos. You play the piano. I don't play the piano. I'll tell you what, though. We're going to get some hot ladies to lay down on these suckers. Some hooter waitresses.

[John Holmberg]

Man.

I'd pay for that right now.

[Guest/Co-host (possibly a sports personality)]

We should have saved this for.

[John Holmberg]

We're on the air, though, for the show. We can still do it.

[Guest/Co-host (possibly a sports personality)]

We'll do it.

[John Holmberg]

Sure, sure. The show that you're on.

[Guest/Co-host (possibly a sports personality)]

I thought we were saying that.

[John Holmberg]

Oh, we can if you want.

[Guest/Co-host (possibly a sports personality)]

I haven't told anybody New Year's. Oh, you haven't?

[John Holmberg]

Well, I told Not. Well, you're on it. That's fine. But I haven't told anybody the special.

[Guest/Co-host (possibly a sports personality)]

Why have New Year's Eve at the Tempe. New Year's Eve at the Tempe Improv. 6 and 8pm 6 and 8:30. So you can be in bed before.

[John Holmberg]

Yeah, you don't need all that nonsense.

[Guest/Co-host (possibly a sports personality)]

I don't like the late night. My shows always fill up earlier anyway.

[John Holmberg]

Six New Year's Eve, eight New Year's Eve. So you can finish up.

[Guest/Co-host (possibly a sports personality)]

It's at 8:30.

[John Holmberg]

Yeah. And so at 8:30 you'll be done by 10:30. Eleven. Yeah. And then you got New York right there.

[Guest/Co-host (possibly a sports personality)]

It's the New York New Year's Eve.

[John Holmberg]

Perfect. So, yeah, you can do New Year's at Tempe Improv with Frank. You can get tickets to Tempe and Prev dot com. That's a good. That's good because you can start your night with some. Because they're always trying to kill time from like 6 to 11. Yeah, that's a perfect way to have like a great.

[Guest/Co-host (possibly a sports personality)]

In Wisconsin, we used to go see the Globetrotters.

[John Holmberg]

I'm doing this as Groovy Globetrotters man.

[Frank Caliendo]

Curly Neil, he could dribble on one knee.

[John Holmberg]

That was your family's New Year's Eve.

[Guest/Co-host (possibly a sports personality)]

We went a couple times.

[John Holmberg]

The Globe Trotter basketball, then home. Some shrimp. Shrimp. Well, I just calling.

[Guest/Co-host (possibly a sports personality)]

Some food.

[John Holmberg]

Some food. Yeah. I just assumed you guys ate a lot of shrimp. Kept small. That would be smelt smell. Baby food for baby people. Yeah, like little people.

[Frank Caliendo]

Baby people.

[John Holmberg]

It looks big in your hands.

[Frank Caliendo]

Like a stage.

[John Holmberg]

Yeah, yeah. And then you had some champagne and everybody went to bed. But it was After a regaling night with Curly Neil and Meow Lemon.

[Brady from HMS]

Some cheese. Had some cheese too.

[Guest/Co-host (possibly a sports personality)]

Meadowlark was gone by then. It was trying to.

[John Holmberg]

I'm. Well, he was probably after Metal Art, got in a fight with the Globetrotters, came here and started the Harlem All Stars. Oh, they came on our show. Curly was part of it, but he couldn't walk. So he was just there because they were mad. So he asked if I'd be on the other team for the night of the game. I played against Washington. I didn't call them that. They didn't. They were a YMCA sponsored team. And so they're like, would you want to come play? And I'm like, I'll come out there. I had five points and the very. But walking out there, Meadowlark Lemon legend is standing next to me before we all run out onto the court and he goes, hey, man, grab this ball right here. And when we go out there, just fire it up from 3 quarters. Can you hit that? And I'm like, watch this. And I'm like, I can. I can come close. I probably won't hit it. He goes, yeah, just do it. People love it. He said, if you miss, they laugh. I'm like, that's fine. I'll take that shot. So I run out there with the ball and I go to do the three quarter. I'm the first one out. Three quarter shot. And it was weighted.

[Guest/Co-host (possibly a sports personality)]

Oh, man.

[John Holmberg]

And this thing starts to go do wobble 12, 15ft to the right. And I'm watching. I'm like, that ball has a weight and you can't. It's not wobbling, but it's not doing stuff right. And it looks like I just threw it at the front row and he just started laughing. He gives me two fingers like, you mother, you should have thrown some confetti at him. And then a dude who smelled like weed named Skywalker jumped over me.

[Guest/Co-host (possibly a sports personality)]

Was it Kenny Skywalker?

[John Holmberg]

No, it wasn't. It was another dude. Different Skywalker. Different Skywalker. Luke. Yeah, it was Luke Skywalker. Yeah. No, he was coming at me and I'm backing up on a break and I just heard him go, move. And I tried to move, but before I could get out of the way, two knees were next to my head. So I just kind of stood still. And when I turned around, he had one arm in the basket and the other arm putting the ball, and he was hanging by his elbows. He could jump that high.

[Guest/Co-host (possibly a sports personality)]

I remember the. The guy who took over for Meadowlark Sweet. Louis Lou Dunbar.

[John Holmberg]

Yeah. Oh, he was great too. He could. He could.

[Guest/Co-host (possibly a sports personality)]

He would put his elbows together and throw the three quarter shot.

[John Holmberg]

Somehow I think it's a weighted ball. After metal art gave me that thing. I think there's a thing. If you just put it close.

[Guest/Co-host (possibly a sports personality)]

His had a magnet.

[John Holmberg]

It might. That's what I'm saying. Something was in the ball I got. Because I would not drone ball the thing I did. I'm like, no, my hands followed through this way. At the very least, it would have been within a foot or two. I'm not kidding. 15, 20ft in the air and it's. And everybody's going.

[Brady from HMS]

Everyone's laughing.

[John Holmberg]

Ugly yellow jersey. So I made it a point to. I had a three pointer and a layup and I got to box out Robert Parrish. This is all in the entertainment drill.

[Guest/Co-host (possibly a sports personality)]

It's entertaining.

[John Holmberg]

That is entertaining. Fraud. Well, Frank's here. He's gonna do the squares with us for promotion for not only your New Year's Eve show over at 10pm Proud, but you're going to be part of Holmberg After Dark, which is next Friday, if you can believe it. We gotta get exciting. We need to start planning something.

[Guest/Co-host (possibly a sports personality)]

Do we know. Are you saying other people that are on?

[John Holmberg]

Well, you just kind of did. But no, you can put Lovets in there. I'm fine with that. The special guest. The guest of the year.

[Guest/Co-host (possibly a sports personality)]

The reason that my wife wants to come.

[John Holmberg]

Exactly. The Frank Kelly.

[Guest/Co-host (possibly a sports personality)]

The only reason she'll come.

[John Holmberg]

The third annual Frank Caliendo. Morning sickness. Guest of the year. An award you've never, never gotten. Yeah.

[Guest/Co-host (possibly a sports personality)]

And never will.

[John Holmberg]

It's named after you, but you've never won.

[Guest/Co-host (possibly a sports personality)]

My namesake.

[John Holmberg]

That's right. It's as if Oscar.

[Brady from HMS]

It came close.

[Guest/Co-host (possibly a sports personality)]

It's like when you have the entertainment.

[John Holmberg]

Drill never music plan, but it never happens. You just. You're in it, but you're not part of it. It's brought to you by our friends@react defense.com. this entertainment drill that we're going to do. Brady, what do you got for us?

[Brady from HMS]

Let's get to the David Byrne from Talking Heads.

[John Holmberg]

Yeah.

[Brady from HMS]

Put together a holiday playlist for people who hate Christmas music.

[John Holmberg]

Oh, geez.

[Brady from HMS]

We got number one is Santa Claus Never comes to the ghetto. I like Yellow Man. Fat Man's Coming by David Byrne. He put his own sure song on there.

[John Holmberg]

Batman's Coming. Something you don't want to search.

[Brady from HMS]

Santa is a Gay man by Big Freedia.

[John Holmberg]

Now give him a listen, Brett, and we'll. We'll take your word for it.

[Brady from HMS]

Yeah, I've been a good girl. Macy. Macy Gray.

[John Holmberg]

Nobody wants to hear her sing.

[Guest/Co-host (possibly a sports personality)]

That's a fun list.

[John Holmberg]

Yeah, that is a fun list.

[Guest/Co-host (possibly a sports personality)]

That's a great one.

[John Holmberg]

You guys want to hear Fat man coming? Never ever.

[Brady from HMS]

And the mass scene is returning on January 7th.

[John Holmberg]

Oh, you're not laughing at John Madden. Just firing a load at us here on the radio. Got a little on you over there and boom. Did somebody get a towel? It's Merry Christmas. Fat man coming.

[Brady from HMS]

Now.

[John Holmberg]

Here's a guy getting an old Fashioned.

[Brady from HMS]

I got flocked.

[John Holmberg]

Here's a towel. Merry Christmas.

All right, finish it up.

Got a little on the ornament there.

[Brady from HMS]

So the Masked Singer.

[John Holmberg]

That's a tree top.

[Brady from HMS]

January 7th, there will be an Ozzy Osbourne tribute night.

[John Holmberg]

Oh, okay. For who on the Masked Singer?

[Brady from HMS]

Yeah.

[John Holmberg]

Wait, like Anna Gastire is going to sing Ozzy songs in a man?

[Brady from HMS]

They don't say who.

[John Holmberg]

Oh, we know who.

[Brady from HMS]

Kelly's gonna be out there as a guest judge. No, but they've got some new costumes. They've. They've said they're gonna.

[John Holmberg]

They asked you to do that ever? No, I did Wife swap.

[Guest/Co-host (possibly a sports personality)]

Wasn't that one that they wanted me to do? The celebrity wife swap. And I was one of the managers at the company was like trying to talk me into it and I almost got talked into it and then I found out I was the country bumpkin family. It was a New York model and I was the loser family. And I was like, see, this is why you don't do this.

[John Holmberg]

This is the never gonna happen matchup of Frank with the super 6 foot 3 inch New York model.

[Guest/Co-host (possibly a sports personality)]

Listen, I already got my model.

[John Holmberg]

And then you're. Exactly. And then your wife would go off with some handsome man married with a six foot model. That was the real threat of that show is that you'd lose twice.

[Guest/Co-host (possibly a sports personality)]

Yeah, the whole thing is shrek.

[John Holmberg]

All right, let's finish that up. We got the Guadalupe squares here. Quick one. We believe we have.

After Dark tickets. I think that's something we've got. So you can come to the show next week. By the way, those tickets are almost all sold out completely. So homework after dark's available somewhere. 98kpd.com you can go over the. I don't know, CB live. Is that what it's called or something? No, no, no, that's right.

[Guest/Co-host (possibly a sports personality)]

Stand up live.

[John Holmberg]

I don't know where it is. This. I'll figure it all out next week. That's when I do stuff. But yeah, we'll give those and crew tickets. How about that. All right, good. You can win those. So we need a boy, we need a girl. 585-9800 and we'll play the squares next. Arizona's most powerful powerful rock radio station.

Can you repeat a?

[Brady from HMS]

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[John Holmberg]

Three employees and two work trucks.

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[Dick Toledo]

They sure are.

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[John Holmberg]

Shockingly low, huh?

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[Frank Caliendo]

Do you get it?

[John Holmberg]

I got it.

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[John Holmberg]

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