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

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.

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)

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)

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).

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)

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)

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)

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

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.

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.