Holmberg’s Morning Sickness – Guad Squares w/Frank Caliendo (12-19-25)

Podcast: Holmberg’s Morning Sickness – Arizona
Episode: Guad Squares – w/Frank Caliendo – Biden, Alec Baldwin, Jay Leno, Morgan Morgan and Morgan, Dairy Dreamer Brady, Barkley and Shaq (01-20-23 – BO)
Date: December 19, 2025

Episode Overview

This episode is a raucous, highly comedic installment of the signature “Guadalupe Squares” game on Holmberg’s Morning Sickness, featuring master impressionist Frank Caliendo as a special guest. The show’s cast and Caliendo rotate through rapid-fire celebrity impressions—Joe Biden, Alec Baldwin, Jay Leno, Morgan Freeman (and more)—while bantering, riffing, and ad libbing in a send-up of the classic Hollywood Squares format. The tone is irreverent, off-the-cuff, and deeply satirical, with much of the humor emerging from running jokes and exaggerated impressions.

Key Discussion Points & Segments

[01:12] Introduction to Squares (“Caliendo Birthday Squares”)

• Mo Bergeron hosts this edition, introducing the squares with "It's the Caliendo Birthday Squares. Mo. Ost away."
• Frank Caliendo jumps in and out of impressions, setting the comedic tone.

[01:38–05:36] Top Left Square: Joe Biden

• Frank, as Joe Biden, launches into a rambling, off-the-rails monologue blending Bidenisms, mangled catchphrases, and confusion with pop culture references.
• Memorable quote:

  “When I was a young man, I missed the scrapp of Pennsylvania. … 500 years ago was the fall of the Roman Empire. What?” (01:41)

• He humorously confuses himself with characters from The Office and The Jeffersons, weaves in political jabs, and gets prompted repeatedly by Mo to “move on.”
• Standout moment:

  “Mo, you smell like Prell.” – Biden (04:04)
  “I worked at an office. We were in a paper company. That's right. Michael Smith. Sniff the girls.” (02:04)

[05:46–06:23] Top Middle Square: Alec Baldwin

• The Alec Baldwin impression delivers dark, meta jokes about his infamous troubles, the “Match Game” and recent controversies.
• Notable exchange:

  “I'm probably going to jail.” – Baldwin (05:51)
  “Maybe you shouldn't have pulled the trigger.” – Mo (06:08)
  "The gun wasn’t loaded. I was." – Baldwin (06:09)

[06:23–07:59] Top Right Square: Jay Leno (as Freddy Krueger)

• Jay Leno riffs on his face being burned, merging Leno with Freddy Krueger for a surreal square.

  “What's the deal? Have you seen this thing? … This guy? What do you mean?” (06:27)

• Inside jokes about Thor, Morse code (“Norse code”), and Leno’s trademark chin.

[08:03–09:39] Middle Left Square: Morgan Freeman & Tracy Morgan

• A recurring sketch with Morgan Freeman, Tracy Morgan, and legal ads for “Morgan, Morgan & Morgan”—devolving into absurd sexual innuendo and running gags about their law practices.
• Highlights:

  “In a wreck. Need a check? Call Morgan. Morgan & Morgan.” – Freeman (08:25)

[10:03–11:09] Middle Square: Dairy Dreamer Brady

• Brady describes his regimen of eating cheese before bed, resulting in nightmares featuring only Jay Leno (“Leno, Krueger and my cheese nightmares”).
• Quote:

  “I ate some port salou and I had a cheesemonger store. … It was a cheese mongoloid.” (10:15)

[11:09–13:40] Center Squares: Ron Wolfley, Jesse Ventura, John Madden, Bill Walton, and Barkley & Shaq

• These squares descend into voice mashup chaos—multiple sports broadcasters and athletes all at once, parodying their signature broadcasting styles.
• Barkley:

  “Brady’s penmanship is like a Joe Biden speech. You can’t get through it without a trail off and misunderstanding what it actually is.” (13:08)

[14:02–16:41] Playing the Game: Questions, Morgan Freeman Banter

• Callers Darcy and Donnie play to win. Morgan Freeman continues joking about legal services and bodily mishaps.
• Memorable moment:

  “Did your vaginal mesh explode and fall out again? Don't call us. Call Erna and Rowe or something.” – Morgan Freeman (15:02)

• They launch into Shawshank Redemption-style narration with donkey jokes:

  "That's when a tall drink of water named Donkey Dufresne… hung down like a tripod..." (17:08)

[17:58–21:52] Continued Gameplay: Biden Returns, Land Borders, Secret Square

• Back to Biden for more word salad and confusion:

  “Are you buffering?... Sometimes you look at me. See a little spinning circle…” – Biden (18:18)

• Trivia question ("The world's longest land border: Russia and China, true or false?"). The answer is false (correct: US and Canada).
• Secret Square clues parodying Guy Fieri:

  “He’s got 2000 seasons of triple D. His clothes scare Jay Leno.” (21:03)

[21:52–23:34] Ending Chaos and “Everyone Wins”

• Improv crescendo—“everybody wins,” Metallica tickets for all, general nonsense.
• “So who really won? I don’t know. America. One word. United States. Big winners. Blast. It’s over. Shut the door. Shut it again. Wrong way. Still in here. Now I’m trapped in a giant cube. Can we be friends? Does this scare you?” (23:34)

Notable Quotes & Jokes (with Attribution)

• Joe Biden (Frank Caliendo):

  • “When I was a young man, I missed the scrapp of Pennsylvania. ... 500 years ago was the fall of the Roman Empire. What?” (01:41)
  • “Mo, you smell like prel.” (04:04)
  • “Sometimes you look at me, see a little spinning circle. Leg timer.” (18:18)

• Alec Baldwin:

  • “I'm probably going to jail.” (05:51)
  • “The gun wasn’t loaded. I was.” (06:09)

• Jay Leno:

  • “Have you seen this thing? Have you seen this Alec Holdren fella?” (06:27)

• Morgan Freeman:

  • “In a wreck. Need a check? Call Morgan. Morgan & Morgan.” (08:25)
  • “Did your vaginal mesh explode and fall out again? Don’t call us.” (15:02)

• Charles Barkley (on Brady):

  • “Brady’s penmanship is like a Joe Biden speech. You can’t get through it without a trail off and misunderstanding what it actually is.” (13:08)

Timestamps for Key Segments

• 01:12 – Mo introduces the “Caliendo Birthday Squares”
• 01:38-05:36 – Joe Biden square, classic Caliendo riffing
• 05:46-06:23 – Alec Baldwin humor and meta-jokes
• 06:23-07:59 – Jay Leno/ Krueger square, “Norse code” joke
• 08:03-09:39 – Morgan Freeman & Tracy Morgan legal absurdities
• 10:03-11:09 – Dairy Dreamer Brady’s cheese nightmares
• 13:08 – Barkley roasts Brady’s penmanship
• 14:02-16:41 – Call-in game, Morgan Freeman “law” and Shawshank riff
• 18:18 – Biden’s “buffering” confusion
• 21:03 – Secret Square as Guy Fieri
• 21:52-end – Everyone wins, episode wraps in comedic chaos

Summary

This Guad Squares episode is a whirlwind of comedic impersonations and improvisation, with Frank Caliendo’s talent and the show’s crew amplifying the zany energy. Satire of politics, celebrity culture, and pop references abounds, with no target too sacred. While the structure loosely follows the Hollywood Squares game, the real entertainment is in the wild character bits, running gags, and fast-paced banter. Fans of improv, pop-culture parody, and sharp wit will find plenty to love—and everyone, in true HMS fashion, goes home a winner.