Podcast Summary: Holmberg’s Morning Sickness – Guad Squares w/ Frank Caliendo (08-22-25)

Overview

In this lively episode of "Holmberg’s Morning Sickness," John Holmberg and the crew are joined by master impressionist Frank Caliendo for a special edition of the infamous "Guadalupe Squares." Today’s version is dubbed "Brady Squares," as morning show regular Brady Bogen becomes the centerpiece for dozens of impressions—some voiced by Frank, most by Brady himself. Expect rapid-fire comedy, playful jabs at co-hosts (especially at Brady and Toledo), and a barrage of celebrity impressions, culminating in a raucous tic-tac-toe game with listeners Paula and David. The show is packed with pop culture parodies, local flavor, and concern (with plenty of dark humor) about Brady’s upcoming kidney surgery.

1. Main Theme and Purpose

• Purpose: To entertain listeners with the recurring game "Guadalupe Squares," this time featuring a smorgasbord of Brady-themed impersonations and an extended appearance by Frank Caliendo.
• Main Theme: Jokingly exploring the many facets of Brady, with the rest of the cast (and Caliendo) riffing via celebrity impressions, culminating in a high-energy squares contest involving two listeners.

2. Key Discussion Points and Insights

A. Introduction and Setup (Skip Ads/Promos)

• Frank Caliendo is in studio, performing locally this weekend ([04:00]).
• The crew teases Brady about his upcoming kidney surgery, turning his health woes into running gags for the episode.

B. Guadalupe Squares – The Brady Edition

• Every Square is Brady: The novel twist—each “square” in the tic-tac-toe parody is Brady doing a celebrity impression or another character, with Frank Caliendo adding several of his own.
• Pop Culture Parody: Frequent references to Back to the Future ("The Frank Capacitor"), Forrest Gump, and more ([06:00]-[12:00]).
• Impression Parade: Notable impressions include:
  • Biden-Brady (“Brady Biden”)
  • John Madden-Brady (“John Madden Bogan”)
  • Trump-Brady
  • Black Lady Brady
  • Tracy Morgan (Frank)
  • John Gruden (Frank)
  • Lord and Savior Tripp Reeb
  • Secret Square: Legendary NFL coach Bill Parcells ([28:30])
• Health Gags: Brady’s kidney surgery is a recurring punchline. The “black lady Brady” character details losing a kidney, “got the sugars on the way,” and upcoming dialysis ([19:40]).

Frank Caliendo (as Tracy Morgan): "I'll put a kidney in you, Brady. Big M, little organ. That's what he needs right now. We gonna stuff that inside you. This dialysis gonna be diabolical." ([21:50])

C. Listener Participation: Paula vs. David

• Paula, the Toledo Hater: A listener known for her pointed dislike of co-host Toledo brings extra spice to the game, even as Toledo is out dealing with family illness ([32:10]).
• Tic-Tac-Toe Goes Off the Rails: Questions in the squares range from odd animal behaviors (“Crows can hold grudges?”) to odd health facts (“Beards offer SPF 21 protection?”), always delivered in the appropriate impression ([46:20]).

Black Lady Brady: “You know why I can’t have lemonade? Cause it’s phosphate. Bad for my kidney. And I got the sugars on the way too.” ([19:40])

D. Memorable Banter

• Frank’s Reluctance: Throughout, Frank exhibits fleeting discomfort at some impressions (especially Black Lady Brady), leading to running meta-commentary on what’s “too far” ([25:40], [56:30]).
• Rapid-fire one-liners and character cross-talk; much is improvised and riffed between Frank and Brady.

3. Notable Quotes & Memorable Moments

• On Brady’s Health:

  “Dear Jim, I’m not feeling well today. I was hoping I could be removed soon. Signed, Brady’s kidney.” – Brady as Rhombogan ([15:00])

• Frank as Tracy Morgan:

  “I can put something inside you, Brady... This dialysis gonna be diabolical. Unfortunately, your kidney's gonna swell up in nine months and make a baby.” ([21:50])

• Black Lady Brady Wisdom:

  “You white people is crazy. House on fire, you gonna sleep through it cause you didn’t smell it, dumbass.” ([41:10])

• Trump Square:

  "I want to build a wall between the squares. I want to paint it black like the Rolling Stones. Too hot for Mexicans to touch." ([13:00])

• On Endings:

  “Have yourselves a great week, Brady. We love you. Be good and stay careful and whatever it is you say to people who are about to die, we’ll kick its ass. Brady will be back when we’re back. That’s a promise.” – Holmberg ([58:00])

4. Timestamps for Key Segments

| Time | Segment | |---------|------------------------------------------------------| | 04:00 | Caliendo’s intro | | 06:00 | Brady as “Frank Capacitor” & time travel parody | | 12:00 | Square introductions (Biden, Madden, Trump, etc.) | | 19:40 | Black Lady Brady sets the tone, talks kidney woes | | 21:50 | Tracy Morgan impression and “diabolical dialysis” | | 25:40 | Frank’s meta-commentary on “too far” | | 28:30 | Secret Square (Bill Parcells) revealed | | 32:10 | Paula (Toledo hater) enters the game | | 41:10 | Black Lady Brady on “white people and fire alarms” | | 46:20 | Brady Biden square, crows and grudges question | | 50:00 | SPF beard question, hair jokes | | 56:30 | Outro banter, upcoming surgery, final wishes | | 58:00 | Holmberg’s closing “kick its ass” speech |

5. Language and Tone

The episode is an uproarious, sometimes edgy blend of improvisational comedy, energetic banter, and deeply irreverent (but strangely affectionate) ribbing among friends. Brady’s health is fair game for black humor, the racial and celebrity impressions teeter on the edge, and Frank Caliendo’s vocal skills shine amid the chaos.

Key Takeaways

• Frank Caliendo enhances the already impression-packed show, even as he is (comedically) a little unnerved by how far the bits go.
• Brady Bogen’s kidney is a theme and a punchline: both a topic of support and endless dark jokes.
• Listener participation in the squares is as hilarious and unscripted as the hosts, especially with Paula’s ongoing vendetta against Toledo.
• The “Brady Squares” concept—morphing one cast member into the voices of everyone—is a highlight for regular listeners and a wild ride for newcomers.
• Despite all the farce, the cast’s affection and support for Brady over his upcoming surgery is unmistakable beneath the jokes.

For New Listeners

If you enjoy fast-paced improv, celebrity impressions, and irreverent banter with a local Arizona twist, this special “Guadalupe Squares” episode with Frank Caliendo is classic HMS—equal parts celebration, roast, and loving sendoff for a key cast member about to face surgery.

Notable Quotes (with timestamps)

• “I want to build a wall between the squares. I want to paint it black like the Rolling Stones.” – Trump (Brady), [13:00]
• “I can put something inside you, Brady... This dialysis gonna be diabolical.” – Frank (as Tracy Morgan), [21:50]
• “You white people is crazy. House on fire, you gonna sleep through it cause you didn’t smell it, dumbass.” – Black Lady Brady, [41:10]
• “Have yourselves a great week, Brady... We’ll kick its ass. Brady will be back when we’re back. That’s a promise.” – John Holmberg, [58:00]

This episode is a fitting sampler of HMS’s signature chaos, high-wire impression work, and deep-fried local color—don’t miss it if you enjoy your morning radio with a side of surgical-grade dark humor.