Holmberg’s Morning Sickness - Guadalupe Squares (11-14-25)

Episode Overview:
This episode features the recurring “Guadalupe Squares” game, with a barrage of celebrity impressions: William Shatner, Bill Clinton, Donald Trump, Michael Caine, Morgan Freeman, Arnold Schwarzenegger, 70s Detective Brady (Columbo), Macho Man Randy Savage, and Tripp Reeb. The squares riff off each other's foibles, current news, and one another’s improvised banter—serving up raw, unscripted morning radio chaos with characteristic irreverence and outrageous humor.

Main Theme

Purpose:
To entertain listeners through the “Guadalupe Squares” (a parody of Hollywood Squares), where hosts improvise as various celebrities and fictional characters, riffing on current events, pop culture, each other, and the absurdity of morning radio.

Key Discussion Points and Insights

1. William Shatner Parody: Tales of Aging and Tumbling

• Shatner is portrayed as both frail and ageless, humorously referencing a supposed “tumble” from the previous night.
• Jokes about vandalizing Denny’s by spray-painting “Crane” (after his Boston Legal character Denny Crane) and ordering “Moons Over My Hammock.”
  • Quote: “Nobody's going to stop William Shatner. Imagine you're at a restaurant and you see outside a tagger. Yikes. ... and then you see that it's William Shatner.” (03:25)
• The running joke is Shatner’s age (94) and falling, contrasted with a stubborn refusal to “take a tumble.”
  • Quote: “Falling down, it's very difficult for us people who aren't stable as we once were.” (03:00)

2. Bill Clinton and Trump Square: Shock Humor and Political Satire

• Portrayals dive into parodic, graphic, R-rated territory, lampooning historical rumors, Epstein, and partisan unity in the most inappropriate ways.
• Clinton jokes about “reaching across the aisle”—now quite literally with Trump.
  • Quote (Trump): “I said I would reach across party lines. Yes. Now I reach around party lines.” (07:06)
• Clinton/Trump riff on their infamous reputations, making increasingly lewd jokes about their relationship.
  • Quote: “Nobody blows like me. Let's be honest. ... You use your hands. I get both hands involved, and you gotta cup those nuts. And he does. I'm telling you what, I didn't need Viagra at all.” (06:07)

3. Michael Caine & Morgan Freeman: AI Paranoia and Actor Voice Rights

• The two characters spar over AI “stealing” voices and impersonation rights.
• Michael Caine warns: “AI is going to take over no matter what we do. ... give it about 16 years before it's taken over our lives.” (08:44)
• They mock-charge three bucks for AI voice rights, riffing on deepfakes and celebrity impersonation.
  • Quote: “Look at me, Corey Dumpling. Okay, here's three dollars. You can be me for three bucks on AI now. Oh, good money. I am an exorbitantly higher price.” (10:01)

4. Brady as 70s Detective “Columbo”

• Brady goes full hard-boiled detective, complete with allergy-sniffly voice, noir-ish monologues, and food references.
  • Quote: “She walked into my office. She had a pair of getaway sticks for miles. She looked at me like I was a glass of lemonade on a hot summer day.” (17:50)
• Extended spoof dialog, with Shatner as the villain: “I would have been probably the guy you liked in the beginning who turned out to be the guy who killed his wife.” (12:14)
• Skewers tropes of the genre, with references to hoagies, “lactating” suspects, and “milk as superpower.”

5. Arnold Schwarzenegger Promotes "Running Man"

• Arnold (impression) obsesses over “Running Man” being shown in theaters again, mixing up Richard Dreyfuss and Richard Dawson.
  • Quote: “Run, Don't Walk to Running Man! ... They show Running Man in the theater again. I just got real excited. There I am running and running ... and then somebody told me, that's not you in this Running Man.” (12:54–13:26)
• Jokes about running away like Toledo’s dad—a recurring in-joke on parental abandonment.

6. Macho Man Randy Savage Birthday Bit

• Macho Man rises from the dead for a birthday celebration, riffing on Slim Jims and his own death.
  • Quote: “No, I was gonna say I'm 20 years removed from my death. ... What you get me? ... Box of Slim Jims. The Macho man approves of the Slim Jim selection.” (15:00–15:19)
• Takes a shot at Toledo's absent dad: “Just like your dad gets you for your birthday every year. Oh, yeah. Thirsty kids.” (15:22)

7. Tripp Reeb (Station Boss) Square

• Jokes about trying to “kill William Shatner for ratings,” wryly referencing the heartlessness of show business.
  • Quote: “We could have gotten some mileage out of killing Shatner. Would you like me to talk to you about it in the office? ... Step into my office. Come follow me fast.” (16:30)
• Exchanges barbs about age and legacy.

Game Play Highlights

• Secret Square: Burgess Meredith, as Mickey from Rocky and the Penguin from Batman (14:04–14:28).
• The game is interwoven with audience call-ins, absurd questions (e.g., stats on kisses and sexual partners), and contestants choosing squares by celebrity character.
• Tongue-in-cheek “questions” often devolve into long, semi-improvised comedic bits before returning to the actual question.
• Brady’s “detective” character riffs wildly, lingering on lewd metaphors: “Everything was fishy ... like a restaurant I probably wouldn’t eat at. Who am I fooling? I’d eat there, the side of the road.” (18:16)
• Banter around “spitter/swallowers” and “sunny D” from the Clinton/Trump block. (21:10–21:57)

Notable Quotes & Memorable Moments

Best Quotes (with Timestamps & Attribution)

• William Shatner [03:25]: “Nobody's going to stop William Shatner. Imagine you're at a restaurant and you see outside a tagger. Yikes. ... and then you see that it's William Shatner.”
• Donald Trump (as portrayed) [07:06]: “I said I would reach across party lines. Yes. Now I reach around party lines. It’s a great thing I’m doing.”
• Michael Caine [08:44]: “AI is going to take over no matter what we do. ... give it about 16 years before it's taken over our lives.”
• Brady/Columbo [17:50]: “She walked into my office. She had a pair of getaway sticks for miles. She looked at me like I was a glass of lemonade on a hot summer day.”
• Macho Man Randy Savage [15:17]: “Box of Slim Jims. The Macho man approves of the Slim Jim selection. Toledo. What do you get me? Nothing, sir. Exactly. Just like your dad gets you for your birthday every year. Oh, yeah. Thirsty kids.”
• Tripp Reeb [16:30]: “We could have gotten some mileage out of killing Shatner. Would you like me to talk to you about it in the office?”
• Arnold Schwarzenegger [13:26]: “Run, Don’t Walk to Running Men. ... I looked at the screen, I’m like, look at me. I look fantastic. Not you. Turns out it’s another guy.”

Noteworthy Segments (Timestamps)

• Shatner’s Denny’s Tagging Story [03:25–04:02]
• Clinton & Trump’s Lewd Cross-Party Partnership [05:16–07:14]
• AI and Voice Rights Debate (Caine & Freeman) [08:42–10:44]
• 70s Detective/Columbo Spoof [11:03–12:48] & [17:14–19:55]
• Arnold Schwarzenegger’s “Running Man” Nostalgia [12:54–13:26]
• Secret Square Reveal (Burgess Meredith) [14:04–14:28]
• Clinton/Trump “Sunny D” Banter [21:10–21:57]
• Tripp Reeb Scheme [16:29–16:54]

Tone and Style

• Wild, unscripted, and deliberately over-the-top.
• Parodic, weaving in references to pop culture, current events, and private show in-jokes.
• Risky, explicit humor; brash, irreverent, and full of absurd improvised asides.
• The tone alternates between mock earnestness and unapologetic bawdiness, maintaining the spirit of "anything goes" shock-jock radio.

For New Listeners

This episode is a master class in improvisational parody and boundary-pushing radio. Expect rapid-fire character changes, edgy humor, and plenty of inside jokes among the crew. If you’re a fan of celebrity impersonations, playful roasting, and unpredictable game show antics, this Guadalupe Squares is peak HMS.