Holmberg’s Morning Sickness: Guad Squares – Smokey Robinson & Shannon Sharpe, JFK, Trump, Billy Bob Thornton, Deaf Brady, OJ, Frank and Sly Stallone

Date: November 21, 2025
Hosts: John Holmberg, Brady Bogen, Bret Vesely, Dick Toledo
Special Episode: The Guadalupe Squares – with celebrity impersonations and irreverent comedy

Episode Overview

This episode of "Holmberg's Morning Sickness" is the show’s signature comedic panel game, "The Guadalupe Squares." Think "Hollywood Squares" with satirical impersonations, wild banter, and tongue-in-cheek humor focusing on skewering pop culture, politics, sports, and themselves. Characters featured include Shannon Sharpe, Smokey Robinson, JFK, Donald Trump, Billy Bob Thornton, OJ Simpson, “Deaf” Brady, Frank & Sly Stallone, and more. The squares are filled with improvised parodies, edgy jokes, and a touch of chaos, all in the show’s typical irreverent spirit.

Key Segments & Discussion Points

Opening Banter & Weekend Plans (01:27–03:24)

• Sports Talk: The guys run down their weekend sports viewing, poking fun at NFL matchups (“Raiders vs. Browns. What a barn burner. Seven vs. two and eight. This is going to be great stuff.” — Holmberg, 02:14).
• Call-back Jokes: Holmberg laments Corey not listening to his appearance mentioned on the Dan Patrick Show, sparking playful back-and-forth teasing.

The Guadalupe Squares Begin

Top Left: Club Shay Shay with Shannon Sharpe & Smokey Robinson (03:31–05:10, 21:24–24:49)

• Shannon Sharpe (parody) launches into his signature “Club Shay Shay” persona—energetic theme song, ribbing and jokes about sexual harassment accusations, and celebrity drama.
• Smokey Robinson joins as the “other sexual assaulter” in the bit, leading to wild, raunchy song parodies and comedic call/response between the two.
• Notable Quote:
  • “Women’s general, they say, they say, Shannon, you done licked me like a salt lick. Against my will. And I said no, I didn’t… Now you got Smokey after the M to the O to the KTE…” — “Shannon Sharpe” (04:00)
  • “If there’s a smile on my face, I’m gonna put it between your legs.” – “Smokey Robinson” (22:07–22:21)

Top Middle: JFK Remembers the Assassination (05:10–06:48, 25:23–26:20)

• Dark Humor: The JFK impersonation centers on Thanksgiving memories, blending food jokes with macabre assassination references.
• Family Traditions: “Don’t forget to have your annual traditional cherry pie with the back blown out of it.” – “JFK” (05:18)
• Conspiracy Theories: “I saw the bullet coming. You cannot see things from behind. I got hit in the throat twice. How do you do that from the back?” (06:11)
• Comedic Resignation: Talks about re-enacting the infamous moment with cranberry sauce and pink dresses.

Top Right: Donald Trump (Impersonation) (06:48–08:39, 16:26–18:52)

• Bragging Rights: Trump’s impersonator boasts about being the best and toughest president because he “got shot and lived,” mocking JFK.
• Put-downs & Braggadocio:
  • “I don’t like the pussy presidents that cry and whine about it with their brains everywhere.” (06:55)
• Jokes about RFK and Kennedy Family: “Both the Kennedy boys—very weak compared to me.” (07:21)
• Game Play: Plays along with panel questions, riffing on Italians (“pistanthrophobia”) and fake trivia.
• Memorable Moment:
  • “You ever get shot in the head? I have... What did Kennedy do? His wife... that’s Jackie, ‘help!’ I didn’t ever say Melania, I said fight fight fight!” (07:12)
  • “I love Italians, okay? I know Brett. I don’t fear Brett. I don’t have any fear of any man. I’m not even afraid of projectiles.” (18:10)

Middle Left: Billy Bob Thornton (& Sam Elliott) (08:39–09:41)

• Deadpan Absurdity: Billy Bob touts his new TV show (“Landman”) and reveals a fake “Boxmasters box set” which is just pictures of women he’s “nailed.”
• Impressions: Includes quick Sam Elliott impression (“Miho”)—the “same exact voice twice.”
• Running Gag: Joke about Columbia House/Publishers Clearing House-style monthly box sets.

Center: “Deaf” Brady (09:47–10:59, 19:14–20:45)

• Physical Comedy: Running joke about not being able to hear anything (“What? What? Wa wa.”), and attempts to do a hard-of-hearing podcast.
• Quote: “The best thing about having no hearing...and that Toledo is just a figure that walks in a room and opens his mouth and I don’t hear it…” (10:20)
• Panel Game: Mishears trivia questions, responds with deadpan one-word “what?” answers.

Middle Right: OJ Simpson (11:04–12:42)

• Bronco Nostalgia: OJ (impersonation) jokes about using John’s Bronco as a getaway vehicle.
• Meta Murder Jokes:
  • “During my murdering years. He (Thriller) would have been an easy kill... Like a lion on a zebra.” (11:19)
  • “You can just go around in that Bronco and, you know, scare the hell out of white women. Pop up out of the backseat like it’s Halloween every day.” (11:46)
• References to Evidence Hiding: Bits about glove compartments, Cato Kaelin, and not needing gloves.

Bottom Left: Brady’s Secret Square – Billy the Kid (12:46–13:13)

• Quick Identifiable Gag: Billy the Kid (impersonation) clues listeners to guess his real name, then backpedals. Jokes about Pat Garrett and Young Guns.

Bottom Middle: Frank and Sylvester Stallone (Impersonations) (13:17–15:17)

• Sibling Rivalry: “Frank Stallone” talks about earning 18 cents in song royalties for “Far From Over”; Sylvester Stallone pops in to dismiss his brother.
• Jabs at Fame: “Go get the chicken, Frankie. Gotta stay outside. Just one more Thriller.” (14:22)
• Supporting Cast: Old “Mickey” from Rocky makes a cameo with classic lines.

Bottom Right: “Trip Reeb” (station general manager, as Lord & Savior) (15:20–16:03)

• In-Jokes: Trip presides as the “Lord and Savior,” giving tongue-in-cheek “approval” and job security to the hosts (“That’s why you’re a good write-off, kid.” (16:00))

The Squares Game Play (16:03–26:28)

• Contestants “Carrie” and “Josh” battle in the classic tic-tac-toe format, picking impersonation-filled squares and answering/agreeing/disagreeing with absurd trivia.
• Running Gags:
  • “JFK” continually references his assassination.
  • “Club Shay Shay” and “Smokey Robinson” ramp up with crude song parodies.
  • “Trump” and “Billy Bob” crack exaggerated jingoist or macho jokes.
  • “Deaf Brady” mangles questions and can’t hear any answers.

Sample Q&A Highlights:

• Trump Square Q: “Pisanthrophobia is a fear of Italian people. True or false?”
  • “Trump” says: “I love Italians… I don’t fear any man. Not even projectiles shot from guns at my head or from Bill Clinton’s wang. I’ve taken them both.” (18:10)
• Brady/Deaf Square Q: “Pirates wore eye patches so their eyes could easily adjust to light changes…”
  • “Brady” riffs on pirates and having no hearing, then says “Pirates wore an iPad so they could look through the telescope.” (20:37)
• Club Shay Shay/Smokey Robinson Q: “Men who kiss their wives before leaving for work live an average of five years longer.”
  • “Smokey Robinson” sings a crude improvisation.
  • “That’s the true. Who cares? Kiss a bitch whenever you feel like it. That’s what I say.” (25:03)

Notable Quotes & Memorable Moments

On Kennedy’s Assassination:

• “Don’t forget to have your annual traditional cherry pie with the back blown out of it.” — “JFK” (05:18)
• “I was there. I saw the bullet coming. You cannot see things from behind. I got hit in the throat twice. How do you do that from the back?” — “JFK” (06:11)

On Trump Taking a Bullet:

• “I said, fight, fight, fight. What did Kennedy do? His wife… that’s Jackie, ‘help!’… I just said, fight, fight, fight. Makes me a better president.” — “Trump” (07:12)

On Club Shay Shay & Smokey Robinson:

• “If there’s a smile on my face, I’m gonna put it between your legs.” — “Smokey Robinson” (22:07)
• “If an 83-year-old man on top of you winning, just lay back and take it.” — “Shannon Sharpe” (22:51)

OJ’s Classic Bronco Bits:

• “You can just go around in that Bronco and, you know, scare the hell out of white women. I’ll pop up out of the backseat like it’s Halloween every day.” — “OJ” (11:46)

Frank & Sly’s Sibling Rivalry:

• “He made 18 cents this morning on the show because you guys played his song…” — “Frank Stallone” (13:21)
• “Go get the chicken, Frankie. Gotta stay outside.” — “Sly Stallone” (14:22)

Deaf Brady on Not Hearing Colleagues:

• “The best thing about having no hearing… and that Toledo is just a figure that walks in a room and opens his mouth and I don’t hear it…” (10:20)

Closing Banter (26:22–28:06)

• Contest winners are announced; both Carrie & Josh receive prizes.
• Random food talk: Thanks to “Ranch House Grill” for breakfast.
• Brady “goes deaf” again as food is served, setting up a classic show-ending laugh.

Noteworthy Timed Highlights

• 03:31–05:10: The wild Club Shay Shay opening feat. Shannon Sharpe & introduction of “Smokey Robinson.”
• 05:10–06:48: JFK’s Thanksgiving assassination parody.
• 06:48–08:39: Trump’s shootout with JFK and improv about surviving bullets.
• 11:04–12:42: OJ Simpson’s bizarre Bronco confessions and murder allusions.
• 13:17–15:17: Frank and Sly Stallone’s sibling banter about royalties.
• 21:24–24:49: Smokey Robinson’s raunchy song improv on Club Shay Shay.
• 25:23–26:20: JFK on how long it takes to fall to the earth’s core.

Tone & Signature Style

The episode is frenetic, irreverent, and loaded with parody—never shying from dark, taboo, or self-referential humor. Impersonations are intentionally over-the-top, and improv lines blur the line between character and actor. The team constantly plays off each others’ jokes, riffing and escalating one-liners, with a healthy dose of audience participation and callbacks to classic HMS bits.

For New Listeners: What to Expect

If you haven’t heard Holmberg’s Guadalupe Squares:

• Expect rapid-fire, adult satire—think SNL’s Weekend Update meets Howard Stern.
• Frequent roasting of pop culture, celebrities (especially notorious ones), and even the hosts themselves.
• Recurring bits and characters that reward regular listeners but welcome new ears with outrageous humor.

Skip the salad, but don’t skip the Squares!