Podcast Summary: Holmberg’s Morning Sickness – "Guad Squares" with Frank Caliendo & The Sklar Brothers

Date: August 15, 2025
Guests: Frank Caliendo, The Sklar Brothers (Randy and Jason), plus regulars Brady Bogen, Bret Vesely, Dick Toledo
Notable Segment: Guad Squares (HMS’s comedic take on Hollywood Squares with celebrity impressions)

Overview

This episode of "Holmberg’s Morning Sickness" featured a special comedy round of "Guadalupe Squares," the show’s irreverent spin on Hollywood Squares. The guest roster was stacked with stand-up talent, including impression master Frank Caliendo and comedy duo, The Sklar Brothers. Within a mayhem-filled hour, the squares were packed with impressions, meta-commentary on comedy, and surreal alter-ego conversations. The live comedy energy was ever-present, leading to a fast-paced, joke-heavy episode that truly showcased the improv skills of all involved.

Key Discussion Points & Highlights

1. The "Guadalupe Squares" Format & Kickoff

• John Holmberg introduces the squares with much fanfare, noting the “room is chock full of headlining comedians and Brady. And Thriller.” [05:00]
• The regular crew hosts, with John as the “chancellor” and Thriller as the sarcastic game show host.
• “Even better. Great comedy two weeks in a row. Look at this room.” – John Holmberg [05:10]

2. Improv Chaos & Square Guests

Each square features a comedian (or multiple in character), leading to outrageous interactions:

Top Left Square: The Sklars as Themselves

• Randy & Jason Sklar fill the square with their signature banter and dry sarcasm.
  • “Last night it rained, but it was a dry rain.” – Randy Sklar [07:00]
• Teasing callback: “We’ll be at Desert Ridge Improv this weekend. Best twin comedy in town.”

Top Middle Square: John C. Reilly (Impression), Sklar-ified

• Parodying John C. Reilly, riffing on being “Square brothers.”
  • “We just became Scar brothers!” [07:25]
  • “She’s awesome. We could do this—Let’s go in the garage and be scar brothers there.” [07:33]
• Rapid, character-whiplash as impressions slide between John C. Reilly, Jim Rome, and others.

Top Right Square: Trump Twins (Caliendo and Sklars)

• Frank Caliendo’s Trump is joined by the Sklars for a doppelganger Trump-fest.
  • “It’s a great square, maybe the best square. A lot of great squares, both sides.” – (Caliendo as Trump) [09:15]
  • “Let’s make it the Guadalupe Circles. We deported Dora the Explorer, let her explore Alcatraz.” [09:30]
• Political satire layered with absurd humor: “These squares should be on the White House lawn, July 4th.”

Middle Row Squares: Absurdism Heightened

• The Neesons: Sklars channeling Liam Neeson.
  • “I have a very specific set of square skills…” [10:40]
  • Callback to Sklars’ early career: “Remember our show on ESPN3 or 4…even cheaper seats.”
• Brady’s Kidneys (middle): The show lampoons Brady’s ongoing health saga.
  • “I got the weight of the world on my back here. They gotta yank me.” – Kidney [13:00]
  • “If you squeeze me, barbecue sauce comes out. I am a disaster.” [13:30]
• Kristoff Waltz & Jason: Impressions spiral into sports and Nazi jokes.
  • “You cannot hide from Kristaps Porzingis…he will be in the floorboards.” – Kristoff Waltz [14:10]

Bottom Row: Mayhem Continues

• Brady Secret Square: (David Koresh parody)
  • Hint: “I died in 1993. Waco, Texas. Leader of the Branch Davidian.” [16:10]
• Freeman Square (Morgan Freeman impressions):
  • “We had to climb through 500 yards of the filthiest slop just to be together again. Come out smelling like a Sklar brother.” [18:13]
  • “Tiny Andy Dufresne.” (Mini-impression joke)
• “Tripp Reeb” (as station GM):
  • “A lot of gonorrhea. My name’s Trip, but they called me Drip Reeb in the ’70s.” [19:10]

3. Game Play Highlights: Rapid-fire Banter

Contestants: Shelby and Corey

Sample Square Exchanges

• [23:00] Intelligence and Addiction Question

  • “Intelligent people have higher risks of alcohol addiction. True or false?”
  • Sklars: “You came to the right place. Absolutely right. A hundred and ten percent, maybe more.” [23:40]
  • Shelby: “Well, I love drugs and I’m super smart, so I’m going to agree.” [24:15]
  • (Laughter erupts; Shelby wins the square.)

• [24:30] Bats and Tequila (Trump square)

  • Question: “Bats are responsible for the creation of tequila. True or false?”
  • Caliendo as Trump: “I think that’s Mexicans. I don’t think we call them bats anymore…” [25:08]
  • Shelby, correcting: “They do, for pollination.”
  • Host: “That’s correct, smart lady. She’s a very smart lady.” [26:00]

• [27:20] Genghis Khan, CO2, and The Sklars

  • “Genghis Khan killed, so great guy—beautiful guy, tremendous work—removed 700 million tons of CO2 from the atmosphere. True or false?”
  • “Genghis Khan, let me rock it. That’s all I wanna do.” – Sklar as faux Madeline Khan [27:45]
  • Corey guesses incorrectly (“That is incorrect”; Shelby wins.)

4. Meta-Commentary & Inside Jokes

• The squares frequently break the fourth wall, ridiculing their own segments and making fun of game show logistics.
  • “Have you done this before?” – Square banter when the rules get muddy [23:20]
• End show riffing on Brady’s supposed “last week,” sleep numbers, and the endless Amazon boxes in his house.

Notable Quotes & Memorable Moments

• John Holmberg: “Look at this room. This is your headliners for the next few years. Chock full of headlining comedians and Brady.” [05:10]
• Trump (Caliendo): “We’re gonna make the Straight great again!” (On the “Bering Strait”) [25:30]
• Brady’s Kidney (Impression): “If you squeeze me, barbecue sauce comes out. I am a disaster.” [13:33]
• Shelby (contestant): “Well, I love drugs and I’m super smart, so I’m going to agree.” [24:15]
• Morgan Freeman (Impression): “We had to climb through 500 yards of filth just to be together again…come out smelling like a Sklar brother.” [18:10]
• Tripp Reeb: “My name’s Trip, but they called me Drip Reeb back in the ’70s.” [19:12]

Important Segment Timestamps

| Time | Segment / Highlight | |---------|-----------------------------------------------------------------------------| | 05:00 | Holmberg intro & setup of the special guest lineup | | 07:00 | Sklars in character as themselves and as John C. Reilly | | 09:15 | Caliendo’s Trump square – political satire & comic mayhem | | 13:00 | Brady’s kidney bit: health crisis humor | | 14:10 | Kristoff Waltz impression, NBA/Nazi riff | | 16:10 | “Secret Square” (David Koresh parody) | | 18:13 | Sklar Brothers do Morgan Freeman/Dufresne impression | | 19:10 | Tripp Reeb (station boss) square, “Drip Reeb” in radio’s ’70s heyday | | 23:00 | First gameplay Q: Intelligence and addiction (contestants answer) | | 24:30 | Trump square – bats and tequila question, audience correction/banter | | 27:20 | Genghis Khan and removed CO2 (Sklar banter, contestant goofs) | | 29:00+ | Endgame chaos, plug for Desert Ridge Improv, more inside jokes |

Tone & Takeaways

• Highly irreverent and meta: The cast constantly breaks character to rib each other or the whole premise.
• Impression-packed: Caliendo and the Sklars cycle through celebrities rapidly, sending the game into absurdist territory.
• Arizona comedy showcase: Plugs for local comedy shows are woven in.
• For fans/followers: A treat with callbacks, in-jokes, and references to past skits and local Arizona media culture.

Bottom Line:
If you love rapid-fire, layered improv comedy, celebrity impressions, and a little inside radio-radio chaos, this episode is a tour de force. The Sklars and Frank Caliendo take HMS’s comedic game show to new heights (and depths), ensuring every square is packed with something bizarre, topical, or just plain dumb—and the episode luxuriates in that mayhem.