Holmberg’s Morning Sickness – "Guad Squares" Special

Date: February 27, 2026
Featuring: John Holmberg, Brady Bogen, Bret Vesely, Dick Toledo
Special Guests/Impressions: Bill Clinton, Tracy Morgan, Donald Trump, Barack Obama, Rapture Brady, Robert DeNiro, Mad Dog Russo, and more

Episode Overview

This episode delivers the signature irreverent, rapid-fire humor of Holmberg's Morning Sickness, centered around the popular "Guadalupe Squares" game. Hosts and guests (real and impersonated) riff brutally on politics, pop culture, sports, and each other. The episode features various celebrity impressions and sharp, edgy banter, seamlessly blending absurdity with biting social satire. While much of the show involves the energetic "Squares" game, there’s also plenty of behind-the-scenes riffing, off-topic detours, and memorable character improvisations.

Key Discussion Points & Segments

1. Show Opens and Studio Antics

[00:00–05:00]

• Technical difficulties and the familiar chaos of a live morning show.
• Holmberg teases upcoming events, jokes about staff birthdays, and riffs on being prematurely born.
• Recaps on failed attempts to connect a female caller for the Squares (a running gag).

Memorable Quote

• John Holmberg: "You were 3/4 finished. Now you gotta finish your life that way. C is average, right? A C zygote, anyway." (04:20)

2. Guadalupe Squares Begin

[05:00–12:30]
Hosted by “Thriller” (Corey), each square is "filled" by someone doing a celebrity impression, with players calling in for a chance at Breaking Benjamin tickets.

Top Left: Witness Relocation Bill Clinton

• Clinton (impersonation) jokes about distancing from Hillary over Epstein rumors, doles out old scandal references, ponders running a bagel shop under a new Jewish identity.

• Jokes about Monica Lewinsky, cigars, and the "revenge" he’s waited decades for.

  Bill Clinton: “You killed that cigar. Oh, man, that thing was soaked...” (07:45)
  “I did not realize that fat bitch was gonna keep that dress. But that’s an older story. I’m on to a new fat bitch…” (09:20)

Top Middle: Tracy Morgan

• Talks (in character) about a new, possibly imaginary TV show and rags on Corey for not knowing the title (“Reggie Dinkins”).

• Lots of meta-jokes about TV, old gigs, and streaming.

  Tracy Morgan: “You can download it on the Hulu—and the Paramount Plus, and the Hulu, AND the Hulu..." (11:10)

Top Right: Donald Trump

• Brags about giving a historic State of the Union speech, spins sexual innuendo about being “longest ever,” and delivers digs at Clinton.

• Recaps the “hugged his wife” State of the Union moment with the pungent aside:

  Trump: “When he hugged his wife, I just said very creepily into the mic, ‘You have a good night.’ And it got really weird.” (13:30)

• Roasts Corey’s early birth and his mother with typically sharp Trump-esque barbs.

3. Middle Squares and Surreal Turns

[12:30–20:00]

Center-Left: Obama & "Big Mike"

• Obama references “aliens everywhere” and riffs on Michelle (“Big Mike”) having masculine qualities, alluding to conspiracies.

• Banter about basketball, marital life, and “aliens” in Obama’s house.

  Obama: “Her dick had 12 points… Like getting hit by Big Ben’s pendulum…” (15:20)

• Big Mike voiced for comedic effect, killing with a basketball double entendre.

Center: Rapture Brady

• Expansive improv about time traveling to a wedding in Ohio and "portaling" back.

• Ridiculous breakdown of the wedding food (pinwheels, cheeky noodles) and Biblical marriage rituals.

• Madcap guest appearances (fake Tommy, Brennan), banter about Cincinnati, and “straight weddings.”

  Brady: “Now I will portal back to the studio... Jesus gave it to me. And now I can rapture whenever I want. I’m like a cool Ford truck. I’m a Ford rapture.” (18:10)

Center-Right: Crying DeNiro

• Overwrought, emotional DeNiro bemoaning “Trump ruining the country,” swinging from tough guy to weepy old man.

  DeNiro: “I don’t know if I like it… Donald Trump’s ruining our country. I used to be a pretty tough guy, Brett…” (20:00)

4. Bottom Squares: Sports and Deep Dives

[20:00–30:00]

Bottom Left: Bret’s Secret Square

• Allusions to old DJs from Cincinnati, with various radio nicknames.
• Listeners must guess “who he is” or the character’s real-life counterpart.

Bottom Center: Mad Dog Russo

• Fires off classic March Madness and spring training content, baseball trivia, and “Mad Dog” cadence.

• Recites full 1994 Toronto Blue Jays and 1979 Pirates rosters, mixing fact and comedic errors.

  Mad Dog: “Are [the White Sox] still in the major leagues? Barely. I don’t know what’s going on there…” (26:40)

• Riffs on ESPN, First Take, and Stephen A. Smith, joking about “solving race.”

Bottom Right: Trip Reif

• Joins in for the final rapid-fire segment, tossing crude jokes about missing teeth and offering a signature blend of filth and inanity.

5. Call-In Game Play & Banter

[30:00–50:00]

• Callers Paige and Kevin participate in the Squares, answering trivia on behalf of their “celebrity” square pick.

• Bizarre back-and-forth between the hosts as “Bill Clinton” flirts shamelessly with Paige.

• Classic "HMS" humor: bodily function jokes, sexual innuendo, and roasting each other and the callers.

  Bill Clinton to Paige: “I just got to slide up against a crease, and you’re going to be covered in mayonnaise… And I like mayonnaise.” (41:05)

• “Rapture Brady” gives a scatological breakdown of toilet time stats.

• No topic is too lowbrow—cheeky nods to personal hygiene mix with surreal improvisation.

  Brady: “There’s 440 days a year... 30 hours a day?” (46:15)
  “Well, that’s incorrect then. He was right. I was right.” (46:40)

6. Wrapping Up, Rapid Fire Tangents & Notable Quotes

[50:00–end]

• Jokes about Renaissance Festival plans:

  Holmberg: “There’s nothing better than a 90-degree day and a bunch of people dressed up like it’s 1600.” (52:20)

• Satirical takes on family game shows and racial representation on “Family Feud.”
• Forced spelling of the code word: "nothing" for station giveaways.

Notable Quotes & Moments

• Tracy Morgan: “You don’t question me about entertainment. I’m in show business. You’re not. I am show business. You’re not.” (11:55)
• Obama (on “Big Mike”): “Sort of like one of the people in Thailand on Toledo’s visit… our Larry, Marlock the Arlirian…” (15:40)
• Mad Dog Russo: “You want to talk about March Maddie’s right around the corner. I will tell you all about that next week. Here’s the starting lineups for your St. Joseph’s Night, 1951…” (28:15)
• Brady (“Rapture Brady”): “I can rapture myself right back on my rapture tube. Wherever there’s a Bullfrog Spas—I can teleport.” (44:05)
• Clinton-to-Paige flirting: “Are you chunky? Cause I like them thick. I’m like the guy from Silence of the Lambs. If you’re not a size 14, I’m not interested.” (41:35)

Episode Highlights by Timestamp

• 00:00–04:30: Host banter, show dysfunction, “full term birthday” jokes.
• 05:00–13:00: Squares kickoff, Bill Clinton, Tracy Morgan, Trump impressions.
• 13:00–20:00: Obama/Big Mike, Rapture Brady, DeNiro squares.
• 20:00–30:00: Mad Dog Russo rants, baseball trivia, and more.
• 30:00–50:00: Callers play the Squares; banter, trivia, weird facts (toilets, sex and the brain).
• 50:00–End: Closing tangents, Renaissance Fest jokes, code word wrap-up.

Tone & Style

• Raw, rapid-fire, and unfiltered humor; roasting each other and playing with the boundaries of good taste.
• Equal parts sports talk, pop culture skewering, political impressions, and lowbrow “guy humor.”
• The episode thrives on improvisation and character-driven chaos—the running schtick of impersonations and playful insult comedy defines HMS’s tone.

For New Listeners

If you missed this episode, you’ll find a hilarious, unpredictable game of “Guadalupe Squares,” featuring masterful character work, relentless ribbing, and a pace that rarely lets up. Regulars will enjoy the chemistry and creativity, while newcomers should be ready for irreverence, rule-breaking, and roasted celebrities—real and imagined—at every turn.

Listen if you crave:

• Political impersonations turned up to 11
• Off-the-cuff, sometimes edgy radio comedy
• Arizona-centric in-jokes with universal “guy radio” humor