Holmberg's Morning Sickness – Guadalupe Squares w/ Frank Caliendo (12-05-25)
Episode Theme / Overview
This special edition of "Holmberg's Morning Sickness" centers on the ever-popular "Guadalupe Squares" segment, featuring master impressionist Frank Caliendo. Alongside John Holmberg and the crew (Brady Bogen, Bret Vesely, and Dick Toledo), Caliendo brings his arsenal of celebrity impressions—including Trump, Jon Gruden, Charles Barkley, Dick Vitale, and more—to a rapid-fire, raucous radio game show. The episode blends quick banter, biting satire, topical references, and the show's trademark irreverence, offering listeners a comedy-packed experience led by some of the best (and wildest) impressions in morning radio.
Key Segments & Discussion Points
1. Opening Banter and Set-Up
- [01:21] Frank Caliendo’s New Year’s Eve appearance at Tempe Improv is promoted.
- Corey “Thriller” Walsh is introduced as the honorary “walker” for the Goliath Expedition, intended as an absurd, comedic fitness challenge for the show’s 25th anniversary.
“Thrillers Goliath Expedition, which will be themed…the constant theme song. …We should have you hold a speaker as well that plays this.” – John Holmberg [02:09]
2. Guadalupe Squares Begin – Celebrity Squares & Impressions
The core of the episode features quick, overlapping impressions from Frank Caliendo, with Holmberg and crew poking fun throughout.
Top Left: The Lovitzes
- Frank as Jon Lovitz, riffing with the crew about show appearances.
- Deadpan references to show favorite Megan, disability, and more.
“No, you don’t. We haven’t started the game yet.” – Jon Lovitz (Frank Caliendo) [04:05]
Top Middle: Dick Vitale & Charles Barkley
- Vitale (Caliendo) brings excitable sports jargon:
- “He’s a diaper dandy! He doesn’t know what the game does anymore. Awesome, baby!” [04:32]
- Barkley riffs about male domestic violence and San Antonio women, moving into darkly comic territory.
“I’m the face of male domestic violence. Everyone should feel sorry for me.” – Barkley (Frank Caliendo) [05:16]
“That’s worse than those big old ladies in San Antonio.” – Barkley (Frank) [05:27]
“I haven’t done Dick Vitale in 20 years, baby. I don’t even know if it’s good.” – Caliendo as Vitale, meta-commentary [05:45]
Top Right: Donald Trump
- Caliendo as Trump offers a wild, non-sequitur board game riff:
- Battleship, Monopoly, and “blowing up boats,” shifting into political satire.
- Blends immigrant jokes, video game references, and classic Trump bravado.
“You sunk my battleship! …There’s a lot of boats…Have you ever played Battleship? I just sunk yours. …I’ll sing it again.” – Trump (Frank) [06:53]
“I go out and I find a porn star, and I play a little Candy Land, you know what I’m saying?” – Trump (Frank) [07:27]
“I’m the president of whatever I want to do. …President of the Earth.” – Trump (Frank) [07:52]
Middle Left: Berman and Stephen A. Smith
- Sportscenter’s Chris Berman and Stephen A. Smith go head-to-head.
- Playful banter about ESPN paychecks, exaggerated speech patterns, and morphing into Popeye:
“Nobody circles the bank vault like Stephen…” – Berman (Caliendo) [09:38]
“I’m Papa A Smith.” – Stephen A. Smith (Caliendo) [10:09]
“I’m contemplating it right now and trying to understand in vociferance. …Neither do I. …It’s just words that you make up, and people pay you more for it.” – Stephen A. Smith & Berman (Caliendo) [10:28]
Middle Square: Deaf Brady
- A recurring bit where Brady feigns deafness:
- Comedic misunderstanding, word-mangling, and quips about not hearing the show for a month.
- “What?” jokes repeated for effect.
“In the last month I’ve lost my hearing pretty much the whole way.” – Brady [11:32]
“What? I haven’t heard this.” – Holmberg [11:45]
“I haven’t heard anything on this channel for over a month and a half.” – Deaf Brady [11:53]
Middle Right: John Gruden
- Quick Gruden impression, with the bit mostly referenced for its saturation.
Bottom Left (Secret Square): Larry Bird
- A tongue-in-cheek impression of Larry Bird, with jokes about his Indiana roots and being “69 years old.”
“Never put a white man to guard me. …It’s a waste of time.” – “Larry Bird” (Frank Caliendo) [12:39]
Bottom Middle: Tracy Morgan & Tracy Mormon
- Frank introduces “Tracy Mormon,” Tracy Morgan’s estranged brother, adding a sharp Mormon satire to the Morgan persona, referencing tithing, and the Walmart accident settlement.
- Rapid, escalating improv – includes riffs on “soaking,” religion, Tide pods.
“You always talking about a guy named Joseph Smith? Joe Smith used to always owe me money. …But I was afraid to go to him. And now you worship him!” – Tracy Morgan (Frank) [13:38]
“Somebody’s gonna get soaked.” – Tracy Morgan (Frank) [14:51]
“You can’t eat tithe pods.” – Frank as “Tracy Mormon” [14:26]
Bottom Right: Additional Rotating Squares
- Rapid-fire impressions and comedic meta-commentary on the slowness of some squares.
3. Game Play – Banter with Contestants
- Contestants Tiffany and Don join the Squares at [18:07].
- Confusion and mishaps play up the humor, especially regarding the “Deaf Brady” responses.
- “Are bananas safely radioactive?” becomes an intentionally garbled, nonsensical trivia question.
- Antics regarding slow responses and difficulty hearing.
4. Further Trump Riffs – Political Satire
- Trump square called for the win ([20:26]).
- Outlandishly offensive riffs about immigrants and boats.
- Satirical monologue about the moon being “wider than Australia.”
- Cohesive Trump-impression verbiage, blending insult, egocentrism, and absurdity.
“I’m looking at the moon right now. In fact, I’m going there Friday. …The moon people said to me, ‘Can we come to your country?’ …I said, ‘No.’” – Trump (Frank) [22:29]
“The moon’s very big. Australia’s not. I think the moon is less wide—like Chris Christie is wider than the moon…” – Trump (Frank) [23:36]
Notable Quotes & Memorable Moments
Frank as Trump on game night:
“Trump for the win—just like 2016, 2020, 2024! …There’s one hanging for dear life like Jack from Titanic. Bye bye bye bye!” [20:42]
Barkley’s San Antonio riff:
“That’s worse than those big old ladies in San Antonio. That’s who’s beating up Shaq. …They come after me with their sticks and their big asses…” [05:29]
Stephen A. Smith’s meta moment:
“It’s just words that you make up, and people pay you more for it.” – Stephen A. Smith (Frank) [10:28]
Brady’s recurring ‘What?’ gag:
“What? …I haven’t heard anything… for over a month and a half.” – Deaf Brady [11:53]
Tracy Morgan/Mormon and soaking:
“Somebody’s gonna get soaked. …Tracy Mormon’s gonna soak with you. Oh, man. And with them Tide pods, you’re gonna come out cleaner.” [14:51]
Self-aware commentary:
“We haven’t even started the stupid game yet. Geez.” – Holmberg [17:29]
Timestamps for Important Segments
| Segment | Timestamp | |-----------------------------------------------|--------------| | Introduction, Goliath Expedition | 01:21–03:18 | | Squares Begin (Lovitz, Vitale/Barkley, Trump) | 03:18–07:52 | | Berman & Stephen A. Smith | 08:40–10:49 | | Deaf Brady & Jacksonville Squares | 11:22–12:45 | | Tracy Morgan/Mormon, Soaking | 13:44–15:12 | | Contestant Banter (Tiffany/Don) | 18:07–19:51 | | Trump Square for the Win | 20:26–23:49 | | Tracy Mormon’s Mormon Satire | 24:29–25:43 | | End-of-Show Musical Parody | 26:44–27:52 |
Closing & Tone
The episode is classic “Holmberg's Morning Sickness”: sarcastic, fast-paced, a little reckless, and always playing to the edge of what's acceptable on radio. Frank Caliendo’s live wire impressions keep the energy high, bouncing between sports, politics, and pop culture, with the crew riffing, escalating, and delighting in the chaos—never missing a beat when turning real news or famous personalities into pure parody.
Summary
In this “Guadalupe Squares” session, listeners get a hilarious, slightly unhinged rollercoaster of celebrity impressions, topical zings, and in-jokes tailored for HMS’s longtime audience. Even without having heard the episode, the summary above captures its electric comedic spirit, key moments, and the high points of Frank Caliendo’s tour-de-force vocal shapeshifting.