Holmberg’s Morning Sickness (98KUPD)

Episode Date: August 29, 2025
Segment: Guad Squares – The All Brady Squares (Fat Elvis, Hulk Hogan, Trump, Brady, Lil Sebastian Maniscalco, Kamala Harris BO)

Episode Overview

This episode revamps the show’s beloved “Guadalupe Squares” as a special “All Brady Squares” edition, handing the impression duties (normally John’s forte) over to Brady. The hosts riff on celebrity and political figures, touching on everything from pop culture to impressions and 1970s history, creating a blend of humor and light-hearted competition. The crew mocks the ever-expanding Internet impersonation culture, tests Brady’s comedic chops, and banters through a zany game of trivia and improv.

Key Discussion Points & Segments

Podcast Banter and Set-Up

• (01:47–03:12)

  • John Holmberg explains that Brady has encroached on his impression “turf” and challenges him to helm the squares.
  • John: “So Brady’s looked at that and said, everybody can do this. And he started to do little Sebastian Maniscalco in the golf cart yesterday, which was the strangest thing I’ve ever heard.” (02:35)

• (03:16–03:53)

  • John hosts for the first time ever, introduces the “All Brady Squares” concept, filled with celebrity caricatures.
  • Brett: “This is the first time you’ve hosted, too.”
  • John: “I’ve never hosted the Guadalupe Squares, ladies and gentlemen.” (03:17)

Squares Introduced (Persona List)

• (03:53–04:09):

  • Fat Elvis
  • Hulk Hogan
  • Donald Trump
  • Transparent Brady
  • Lil Sebastian Maniscalco
  • Secret Square (NFL Star)
  • Kamala Harris
  • Tripp Reeb

• (08:09–21:46):

  • The squares game begins, with trivia and banter interwoven as callers (notably Dolores and Anthony) pick squares.
  • Hilarious impressions, including Trump, Biden, Hulk Hogan, and Fat Elvis, are performed by Brady and other hosts.

Noteworthy Quotes & Bits

• On Internet Impression Culture

  • John laments:

    “You get people on the Internet who do impressions, and they're garbage. And people, like, love them. Impressions…they’ve lost their fun to me…Some guy will go on and go, 'Hi, look,' and he's just wearing a wig, and he goes, 'I’m Rudy Giuliani.' It’s like you’re not even doing a voice.” (02:18)

• Fat Elvis' Birthday Confusion

  • John: “It’s your anniversary of when you passed. Or is it your birthday? I don’t remember.” (04:03)
  • Fat Elvis: “It’s my birthday, baby. Maybe. I don’t know.” (04:08)
  • Vince: “You were born in January. Thank you, Fat Elvis.” (04:15)

• Hulk Hogan Endorses Trump

  • Hulk Hogan: “We got a big election, brothers. You know who I’m voting for? Eat your vitamins and vote for America. Making it great again.” (04:22)

• Transparent Brady on Wasabi

  • John: “You were talking about wasabi earlier this week. Being clear. What are you, Japanese? Repeating words. It’s you, for Christ’s sake.” (04:55)
  • Anthony (as Brady): “It’s good to be here. In the square, you go, he’s a person.” (05:08)

• Lil Sebastian Confesses

  • Lil Sebastian (Maniscalco impression): “I mean, driving me nuts. I wish my nuts would drop, you know, so I can walk around.” (05:27)

• Call-in Banter with Dolores

  • Dolores: “I think I actually started the whole butt thing.”
  • John: “You were the one that wouldn’t stop touching my ass.” (07:45)
  • Dolores: “Yeah, how nice it was in the jeans.” (07:53)
  • John: “It’s a good looking ass.” (07:56)

Notable Squares Questions & Answers (with Timestamps)

Transparent Brady (Center Square)

• Question: “65 million years ago, the day actually lasted just less than 23 hours. True or false?”
  • Anthony (as Brady): "That’s absolutely true. Because I was alive to see it." (08:32)
  • Dolores agrees. John: “That is right. X gets the square.”

Hulk Hogan (Upper-Right Square)

• Question: “The first modern Olympic Games in 1896 did not award gold medals to event winners. True or false?”
  • Hulk Hogan: “Well, that’s a great question, brother…The awards that they gave out the oly. It was food, I think. It’s not a medal.” (09:33)
  • John clarifies: “Technically, he’s right. They did not give out gold medals, so I’m going to give it to you — they gave out silver instead, not food.” (A circle gets the square).

Tripp Reeb (Bottom-Right Square)

• Question: “Al Capone’s brother James was an agent for the government during prohibition.”
  • Tripp: “You know what he was…I knew this…today is gonna be lovable…The day that he…” (12:32–12:55)
  • Dolores agrees; John: “That’s exactly right. He did, evidently, work for the government during prohibition.”

President Joe Biden (Upper-Left Square)

• Question: “Until the 1972 Olympic Games in Munich, all gold medals were solid gold.”
  • Biden: "That is not true…They were made from…blob." (13:44–13:54)
  • Anthony answers "That is true."
  • John: “I’m gonna disagree... That is right!” (Zirkel gets the block). (14:17)

Fat Elvis (Center-Left Square)

• Question: “Makeup artists modeled Yoda after Austrian neurologist Sigmund Freud. True or false?”
  • Fat Elvis: “Hey, man, what is a Yoda?..How’s he taste?…I love green chicken. It’s got the wasabi on it…and you know what I do with the wasabi?” (15:22–15:55)
  • Dolores agrees; John: “That is incorrect. We cannot give you the square...” (16:10)

Lil Sebastian Maniscalco (Right Center Square)

• Question: “Ted Williams career batting average of .344 is actually just the 12th best in major league history. Is that true or false?”
  • Lil Sebastian: “344 is pretty good. You know, by the way, Dolores, you rhyme with one of my favorite names. Don’t say that…That answer is true.” (18:24–19:08)
  • Dolores agrees; John: “Incorrect. It is the 6th best batting average, which is still lower than the final square.” (19:18)

Donald Trump (Final Square)

• Question: “In the early 1500s, there was a dancing plague that struck Europe, causing uncontrolled dancing in public. True or false?”
  • Trump: “It was a terrible plague from China. Cause people to dance. I’m gonna say that’s true…It’s Footloose.” (20:11–20:27)
  • Anthony disagrees; John: “That is incorrect. Actually, it was a terrible dancing plague that took over the nation.”

Memorable Moments & Meta Commentary

• Hosts embrace the chaos:

  • John: “Proudly did it. Sixteen squares all dovetailed together.”
  • Vince: “The Bradalupe squares. Heard on a podcast somewhere else. Yes, I like that.” (22:07)

• Roasting Brady’s Impressions:

  • Vince: “How in the world is your impression of Brady better than Brady’s impression of himself?” (06:52)
  • Brett: “This is B.S. Yeah, Brady doing the squares. This is like when the band has the crowd sing the song for them. This is not what we listen for.” (07:00)

• Self-aware humor about “impressions culture”:

  • John (mocking the Internet): “That’s what the Internet sounds like to me. That’s what all these impressions on the Internet sound like to me. Like, why do I try?” (21:46)

• Fat Elvis on “Yoda” Tasting:

  • Fat Elvis: “I love green chicken. It’s got the wasabi on it. And you know what I do with the wasabi?” (15:44)
  • John: “You spread that delicious, clear wasabi.” (15:52)

Episode Structure (with Time Stamps)

• [00:00–01:47]: Sponsor Reads / General Banter
• [01:47–03:16]: Challenge Set-Up – Brady Steps Into the Impressionist Role
• [03:16–05:17]: Introduction of the All-Brady Squares & Characters
• [05:17–08:14]: Impressions, Banter, and On-air Roasting
• [08:14–21:46]: Main Squares Game (Celebrity Questions, Callers, Running Jokes)
  • Includes trivia, improvisation, further bits with Dolores and Anthony
• [21:46–23:36]: Concluding Banter, Future Episode Teasers, Meta Commentary

Summary

This raucous “All Brady Squares” edition shows Holmberg’s crew at their silly, improvisational best, with Brady stepping up as the chief impressionist—delivering take after take on high-profile characters (Fat Elvis, Trump, Hulk Hogan) while trading jabs with the rest of the show. The episode pokes fun at the rise of low-effort celebrity impressions online, and the laughter is constant as the team’s competitive game devolves into pure comedic chaos, making listeners feel like they’re part of an inside joke.

For fans, it’s a showcase of the crew’s humor, quick wits, and ability to riff endlessly—whether on pop culture minutiae, sports trivia, or the absurdities of modern Internet culture.