11-18-25 - Entertainment Drill - TUE - w/Frank Caliendo - List Of Greatest Late Night TV Hosts Of All Time And Riffing On Jay Leno's Fall

Summary

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Podcast Summary: Holmberg's Morning Sickness – Entertainment Drill with Frank Caliendo

Episode Title: 11-18-25 – Entertainment Drill – TUE – w/Frank Caliendo – List Of Greatest Late Night TV Hosts Of All Time And Riffing On Jay Leno's Fall
Date: November 18, 2025
Guests: Frank Caliendo (comedian/impressionist)
Regulars: John Holmberg, Brady Bogen, Bret Vesely, Dick Toledo, Larry McFeely, Byron

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Episode Overview

This episode of Holmberg's Morning Sickness features a lively entertainment drill segment with comedian and master impressionist Frank Caliendo. The show dives into the results of “best late night TV hosts of all time,” riffs about Jay Leno’s recent mishaps, and spins off into classic banter and sharp impressions, all while poking fun at pop culture, sports, and showbiz.

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Main Topics & Key Discussion Points

1. Frank Caliendo’s Upcoming Show & Banter

• Frank announces his New Year's Eve show at 10pm Improv, joking about “lickable” technology and dating in a typical Caliendo absurd style (01:18–02:12).
  • Memorable moment:
    • Frank: "Be nice. You make your own manufacturing... She's lickable. I licked her last night and I'm going out with her again today." (02:10)

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2. Most Hated NFL Teams in the U.S. – Google Keyword Planner Study (02:57–04:42)

• Brady shares info from a Canadian betting site using Google’s keyword planner to determine the most hated NFL teams.
• Top Teams Hated:
  • Cowboys and Steelers tied for #5.
  • Jets and Packers tied for third.
  • Raiders at #2.
  • Number 1: Philadelphia Eagles, hated in 13 states.

Notable Quotes:

• Frank: "Cowboys are tied with the Pittsburgh Steelers at number five." (03:20)
• Brady: "Number one, Philadelphia." (04:31)
• Frank: "The Eagles. Thirteen states. The city of Philadelphia is not beloved by anybody but the brothers there." (04:32)
• Larry riffs on the “Dutch boy” haircut of the Raiders' owner (04:14):
  • Larry: "Dutch boy haircut becomes the epitome whatever that is. It's a microcosm of your organization." (04:15)
• Frank pokes at the Raiders: "The Raiders deserve everything that's happening to them ... they didn't stand up for Gruden." (03:59)

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3. Late Night TV Host Rankings – Ranker.com List (05:16–06:56)

• Brady brings up a Ranker.com poll on the best late night hosts.
• Top Results:
  • #1 Johnny Carson
  • #2 Conan O'Brien
  • #3 David Letterman
  • #4 Craig Ferguson
  • John Stewart, Graham Norton, Ed Sullivan, Colbert, John Oliver, Dick Clark, etc.
• Notably absent or ranked low: Jay Leno, Jimmy Fallon (#20), Jimmy Kimmel (#16).

Great Moments & Impressions:

• Frank jumping in with classic impressions for Letterman and Fallon:
  • Frank (as Fallon): "Seriously, who do I have to kill around here to get good ratings?" (06:07)
  • Frank (Fallon, Joker-style): "If you kill somebody, I'm going quest. Lava cut his head off. Right on. That would be great. And then we'll have Blake Shelton come out and sing a song about it." (06:28)
• On Leno’s snub:
  • Frank: "He worked his whole life and he was number one for 14 years." (06:56)
  • Group riffs on Jay’s style and Groucho Marx's "You Bet Your Life" (07:13–07:20).

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4. Riffing on Jay Leno's Recent Falls & Mishaps (07:33–10:25)

• The crew and Frank go on an extended, riff-heavy improv about Leno’s recent unlucky streak (falling, fires, etc.), using impressions, jokes, and wild scenario-spinning.
• They speculate and joke about the logistics and details of Leno's fall from a hotel down a grassy hill, absurdly dramatizing the event.

Notable Quotes & Impressions:

• Frank (Leno voice): "I'm not fine. My face is a mess. Jeez Louise, that's quite a ... I'm watching him step over there, Mr. Shatner." (08:10–08:15)
• Larry: "It takes something to make this face look worse, doesn't it?" (08:15)
• Frank: "My chin broke the fall. This is good. I was doing chin ups. I was on the ground." (08:27)
• Frank (as various voices): Gets lost in the laundry list of incidents—fires, falls, denim pajamas.
• Caliendo as Jay: "He was running from a hotel room he shouldn't have been in. The husband showed up—I gotta get the hell outta here. Jesus Christ. I'm gonna get killed. I'm fine. Pick me up." (10:04–10:14)
• Brady: "Tripped on the denim cuff." (10:14)
• Frank: "That's the taste of Leno right there. You just had a nice little swipe of Leno on your tongue." (10:21)

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5. Comic Digressions & Pop Culture Riffs (10:25–11:00)

• More spontaneous riffing veers into “He-Man/Cringer/Battle Cat,” with jokes about 1980s cartoons, Google search mishaps, and “lickovision.”

Memorable Exchanges:

• Larry: "What's the deal with Cringer? Have you seen this guy? He-Man points a sword at him and all of a sudden he's Battle cat." (10:25)
• Frank: "Did you see Orko?" (10:34)

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Notable Quotes (with Timestamps)

• "Be nice. You make your own manufacturing... She's lickable. I licked her last night and I'm going out with her again today."
  — Frank Caliendo (02:10)
• "Cowboys are tied with the Pittsburgh Steelers at number five."
  — Frank Caliendo (03:20)
• "Number one, Philadelphia."
  — Brady (04:31)
• "The city of Philadelphia is not beloved by anybody but the brothers there."
  — Frank Caliendo (04:32)
• "Dutch boy haircut becomes the epitome whatever that is. It's a microcosm of your organization."
  — Larry McFeely (04:15)
• "Seriously, who do I have to kill around here to get good ratings?"
  — Frank Caliendo as Jimmy Fallon (06:07)
• "He worked his whole life and he was number one for 14 years."
  — Frank Caliendo (06:56)
• "I'm not fine. My face is a mess. Jeez Louise, that's quite a ... I'm watching him step over there, Mr. Shatner."
  — Frank Caliendo as Jay Leno (08:10–08:15)
• "My chin broke the fall. This is good. I was doing chin ups. I was on the ground."
  — Frank Caliendo (08:27)
• "He was running from a hotel room he shouldn't have been in. The husband showed up—I gotta get the hell outta here. Jesus Christ. I'm gonna get killed. I'm fine. Pick me up."
  — Frank Caliendo as Jay Leno (10:04–10:14)
• "What's the deal with Cringer? Have you seen this guy? He-Man points a sword at him and all of a sudden he's Battle cat."
  — Larry McFeely (10:25)

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Timestamps for Key Segments

• Frank’s Show & “Lickable” Tech Riff: 01:18–02:12
• Most Hated NFL Teams Discussion: 02:57–04:42
• Late Night Hosts Rankings: 05:16–06:56
• Leno Snubbed, More Impressions: 06:56–07:32
• Jay Leno Fall Bit & Impressions: 07:33–10:25
• Cartoon/Pop Culture Riffs: 10:25–11:00

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Tone & Style

• The tone is irreverent, energetic, and playfully mean-spirited—a mix of impressions, satire, and improv.
• Frank Caliendo’s rapid-fire impressions fuel much of the comic chaos.
• The hosts riff off each other quickly, often spiraling into absurd, pop-culture-laden bits.

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Conclusion

This episode is a riot of improvisational humor centered on TV nostalgia, sports, and showbiz. Frank Caliendo’s vocal versatility keeps the crew on their toes and listeners laughing, especially as they deconstruct pop-culture lists and turn Jay Leno’s recent real-life misfortunes into farcical skits. Essential listening for fans of comedy, late night lore, and classic radio banter.

Transcript

[Brett Vesely]

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[Byron]

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[Brett Vesely]

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[Byron]

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[Brett Vesely]

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[Larry McFeely]

Hey, it's Larry McFeely here with my friend Wayne from AMCO. And Wayne, if my car has an extended warranty, do I have to take it back to the dealer for service?

[Brett Vesely]

No, Larry, if you have an extended service contract, you can use it at any amco.

[Larry McFeely]

Well, it's nice to have other options.

[Brett Vesely]

I'll say AMCO has dealership quality rental cars, no hassles and faster service.

[Larry McFeely]

AMCO does more than just transmissions, right?

[Brett Vesely]

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[Larry McFeely]

Just Google AMCO for your nearest location. That's AMCO double A MCO transmissions and a whole lot more.

[Frank Calendo]

All right, let's get the heck out of here. Frank Calendo joined us most the whole morning and he's going to be over at the 10pm Prov for new Year's Eve. Make your New Year's Eve plans now. You can get tickets@10p improv.com buy those tickets and take care of business there. And you'll be out of there at 10:30 about and you go line up.

[Brady]

You'Ll get your New Year's kiss.

[Frank Calendo]

Are you going to do a kissing booth again this year?

[Brett Vesely]

Yeah.

[Frank Calendo]

Or you can get a. Actually a Frank. They have a Frank pod. You can put it in your lickable television like Frank the taste of the mic. Actually be pretty cool like on a date to say this went really well. Do you want to taste me? Yeah, that'd be nice. I'll take no give you. And they exchange tastes. You go home and lick each other on TV and go, I think I want to Stack a date with this one. Be nice. You make your own manufacturing.

[Brett Vesely]

What do you think of her?

[Larry McFeely]

She's lickable.

[Frank Calendo]

She's very lickable.

[Brady]

That's love it.

[Frank Calendo]

She's lickable. I licked her last night and I'm going out with her again today. Anyway, it is time now for Brady to give you all the entertaining news he knows. It's the entertainment drill brought to you by reactdefense.com the Home Tactical Black Self Defense Training their 25th anniversary is here 89 for a month of training and that includes every class they have which is a ton. It breaks down to like pennies per class. If you used all of them, that'd be ridiculous. But if you used all of them, that's what you got. But all your options are sitting right in front of you. And you will get a taste of what it's like to be part of react Defense's tactical black self defense training. Learn how to be a better version of you. Stop being a sheep. Start being a sheepdog and keep the wolves at bay. ReactDefense.com is the home of tactical black Brady.

[Brady]

Entertain me a Canadian sports betting website. Use the Google keyword planner to figure out which NFL team is the most hated in the US Hated. Yep.

[Larry McFeely]

Patriots.

[Frank Calendo]

Cowboys. Raiders.

[Brett Vesely]

Patriots were but I don't know about anymore.

[Brady]

Patriots are no longer on the list.

[Frank Calendo]

Not on the list.

[Brett Vesely]

Say Cowboys are Raiders.

[Brady]

The Cowboys are tied with the Pittsburgh Steelers at number five.

[Frank Calendo]

Steelers are in the top five. Success.

[Larry McFeely]

Success.

[Brady]

There's a tie for third place.

[Frank Calendo]

Packers.

[Brady]

The jets and the Packers.

[Frank Calendo]

Yeah.

[Brady]

Six dates.

[Frank Calendo]

First place would be the Eagles.

[Brady]

So Cowboys and the Steelers are most hated.

[Frank Calendo]

Chiefs three states and three states it's.

[Larry McFeely]

Got to be the Chiefs, Eagles and Ravens.

[Frank Calendo]

You know what? He's probably right. The the Chiefs been annoying and now yeah, they hate winning and tay tay.

[Brady]

And jets and Green Bay packers were six states hated. Las Vegas Raiders are numbers two, eight.

[Larry McFeely]

Not when I was coach man.

[Frank Calendo]

You know what? And I was watching that. We talked about it off there a little bit. The Raiders deserve everything that's happening to them as far as just a franchise that is in futility because they didn't stand up for Gruden.

[Larry McFeely]

I'll tell you what man. I what I look to is the owner's haircut.

[Brady]

Yeah.

[Frank Calendo]

You can't have an owner with that.

[Larry McFeely]

Dutch boy haircut becomes the epitome whatever that is. It's a microcosm of your organization.

[Frank Calendo]

Just a poor haircut.

[Brady]

On the map I don't see one state of Kansas City Chiefs.

[Frank Calendo]

Who is number one?

[Brady]

Number one, Philadelphia.

[Frank Calendo]

The Eagles. Thirteen states current champions. Usually that's pretty high up. And the city of Philadelphia is not beloved by anybody but the brothers there.

[Larry McFeely]

Oh, guys, I just signed in to Coinbase from Moscow.

[Frank Calendo]

Oh, why?

[Larry McFeely]

I don't know if this is not me, I gotta contact an 800 number. I gotta go lick it.

[Frank Calendo]

Lick it.

[Brady]

Timothy Chalamet told Adam Sandler he deserved an Oscar for Punch Drunk Love.

[Larry McFeely]

Thanks, big guy.

[Frank Calendo]

Adam said, but you didn't even perform in that movie. I should have gotten the Oscar. You don't understand what I'm saying. You do not take your baskets for my films.

[Brady]

We got another list. Ranker.com did the best late night hosts of all time.

[Frank Calendo]

Well, this is easy.

[Brady]

Yeah.

[Frank Calendo]

Carson number one. Letterman.

[Brady]

Letterman number three.

[Larry McFeely]

And you're in your left hand, the top five list.

[Frank Calendo]

Hi.

[Brady]

Dave coated O' Brien number two.

[Frank Calendo]

The generation of people in their 50s.

[Brady]

Then number four was Craig Ferguson. John Stewart, Graham Norton, Ed Sullivan.

[Frank Calendo]

Wow. Jaylen was nowhere near this.

[Brady]

Stephen Colbert. Wow. John Oliver, then Dick Clark. That's the top ten.

[Larry McFeely]

What was one?

[Brady]

Johnny Carson?

[Frank Calendo]

Oh, yeah.

[Byron]

Coming in.

[Frank Calendo]

This is the standard answer. I think. I don't think.

[Brett Vesely]

Joe Fallon.

[Frank Calendo]

Wow.

[Nick Toluto]

Yeah.

[Frank Calendo]

Where's Jimmy? Oh my God.

[Brady]

Jimmy Kimmel, 16th. Jimmy Fallon, 20th.

[Frank Calendo]

Seriously, who do I have to kill around here to get good ratings?

[Larry McFeely]

My band leader.

[Frank Calendo]

I killed Quest Love last night. Well, maybe if I cried like that. Kimmel. What are you laughing at? I'll kill you too. I. I've made him angry now Angry. Off the air, Fallon is furious.

[Larry McFeely]

Angry, funny. Fallon angry, laughing, angry.

[Frank Calendo]

Oh my God. I just killed again. He's a serial killer with a joker. Yeah, he is sort of the joker. My God, I keep losing my ratings of these idiots. If you kill somebody, I'm going quest. Lava cut his head off. Right on. That would be great. And then we'll have Blake Shelton come out and sing a song about it. Yeah. I don't get. Fallon's not on there and Leno's not on there, which is surprising.

[Larry McFeely]

You said Fallon was like 20th or.

[Frank Calendo]

Something, but you didn't say Leno at all.

[Larry McFeely]

What's the deal with this?

[Frank Calendo]

True story.

[Brady]

True story.

[Frank Calendo]

He worked. He worked his whole life and he was number one for 14 years.

[Brady]

What's the deal with this?

[Larry McFeely]

You guys see this?

[Frank Calendo]

Yeah.

[Larry McFeely]

Here's the thing.

[Frank Calendo]

Hey, Jay, did you see.

[Larry McFeely]

You're not even in the list. And I'm not sure that I also do that show where it looks like I just got out of bed and I'm in my jean pajamas.

[Frank Calendo]

The. The Groucho Marx. You bet your life.

[Nick Toluto]

Yeah.

[Larry McFeely]

You bet your life. Yeah. What's to do with that? Have you tried this? Have you tried this?

[Brett Vesely]

The.

[Larry McFeely]

Yeah, you get pajamas and they may not have done them. Have you ever tried that denim PJ. Denim, PJs, DPJs. That's a lot dirtier than it is.

[Frank Calendo]

It's. True story. True story.

[Brady]

He's all bruised up.

[Frank Calendo]

Did he fall again? Oh, my God.

[Larry McFeely]

You guys know I filled in for him that show right?

[Frank Calendo]

When he fell down.

[Byron]

No, no, no.

[Larry McFeely]

When he caught on fire.

[Frank Calendo]

Oh, that's right. When he fell down.

[Larry McFeely]

When he caught on fire. I had to sub for him in Vegas.

[Frank Calendo]

Yeah. It's like a Michael Jackson. That felt like, whoa, whoa. I'm trying to get over to my show. And as I fell down this ramp over here like slippery grass. And I'm. Play that sound effect for me, Mr. Shatner. No.

[Brady]

I'm fine. Pick me up.

[Frank Calendo]

I'm not fine. My face is a mess. Jeez Louise, that's quite a. I'm watching him step over there, Mr. Shatner.

[Larry McFeely]

And it takes something to make this face look worse, doesn't it?

[Frank Calendo]

I tell you what, you land on this face and you know. Oh, yeah, yeah, yeah.

[Brett Vesely]

Why?

[Larry McFeely]

I was comforted by the fall from my chin.

[Frank Calendo]

My chin broke the fall. This is good. I was doing chin ups. I was on the ground. But still the. The amazing thing, especially where the fell.

[Brady]

The fall happened.

[Frank Calendo]

Yeah. Because he walked from a quartz or like.

[Nick Toluto]

What are those?

[Larry McFeely]

I honestly believe it. 100.

[Frank Calendo]

I do not.

[Larry McFeely]

Because I've been on those, Those hotels. Those hotels.

[Byron]

Right?

[Brady]

There you go.

[Byron]

You.

[Larry McFeely]

You go right down there up on the.

[Frank Calendo]

He didn't have a car.

[Brady]

I'll take a shortcut.

[Frank Calendo]

Of all people do not have a car.

[Larry McFeely]

No. Because they drop you, pick you up and drop you off.

[Frank Calendo]

I still don't buy it. He went from a. A courtyard Marriott down a slippery grass hill.

[Larry McFeely]

It's. I've been right there.

[Frank Calendo]

And they drive you from the Marriott to the show.

[Brady]

What it sound like when you went down the hill first?

[Frank Calendo]

Yeah. Did you have a Morgan Freeman? My voices, my life voices are flashing in front of me.

[Larry McFeely]

I tell you what, man.

[Frank Calendo]

I tell you what.

[Brett Vesely]

This gu.

[Larry McFeely]

Screwed me over, man.

[Frank Calendo]

That's a big hill.

[Larry McFeely]

Speaking of hills, here's my Henry Hill. What are we talking about here, huh?

[Frank Calendo]

Is that what we're doing? Is that what we're doing here? Wow. So you're saying Jay Leno goes. Well, it looks like it's time for the show. I should probably hoof it over to the arena.

[Larry McFeely]

I went down to get something to eat.

[Frank Calendo]

Oh, it was down. I've done it.

[Larry McFeely]

I've done that same move.

[Frank Calendo]

Nobody got Jay Leno a sandwich. He had to walk down a big hill.

[Larry McFeely]

There aren't higher level hotels. There's like Hampton Inns.

[Frank Calendo]

And from the Hampton Inn I'll squeal down this grassy knoll.

[Larry McFeely]

I know, I know it sounds weird, but I've done the same move.

[Frank Calendo]

He was running from a hotel room he shouldn't have been in.

[Larry McFeely]

He was wearing.

[Frank Calendo]

The husband showed up. I gotta get the hell outta here. Jesus Christ. I'm gonna get killed. I'm fine. Pick me up.

[Brady]

Tripped on the denim cuff.

[Larry McFeely]

Try my lickovision there.

[Frank Calendo]

That's the taste of Leno right there. You just had a nice little swipe of Leno on your tongue.

[Larry McFeely]

What's the deal with Cringer? Have you seen this guy? He man points a sword at him and all of a sudden he's Battle cat.

[Frank Calendo]

Huh? What's the deal there?

[Larry McFeely]

Did you see Orko?

[Frank Calendo]

Sorry, Jay. All right, let's get out of here. That's insane. Anyway, somebody pointed out what I heard too. So did Brady just call Google gorgle or gurgle? Like gurgle. Don't sear gurgle on Google. You're gonna get through liquision faster than you want. Frank, thanks for popping in this morning. It was fun to share the near death experience of an icon in America with you.

[Brady]

It's great to see you.

[Frank Calendo]

It's wonderful to be good, to be a part of this. That's right. And we'll be part of more later. Frank's at 10pm for New Year's Eve. Get your tickets there. We're all done. You guys enjoy Larry and we'll see you tomorrow on the Morning Sickness. It's out of control now. Hey, it's John Holmberg 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 equation lifechangerloan.com 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. Lifechangeloan.com It's Nick Toluto from Homer's Morning.

[Nick Toluto]

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