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.

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.

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)

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)

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 |

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.

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.