Podcast Summary: Holmberg's Morning Sickness – Guadalupe Squares: NFL Season Edition

Date: September 5, 2025
Podcast: Holmberg's Morning Sickness (98KUPD, Arizona)
Format: Comedy game show—with sports and pop culture satire
Hosts: John Holmberg, Brady Bogen, Bret Vesely, Dick Toledo
Special Feature: The Guadalupe Squares—NFL Season Edition

Overview

This episode combines Holmberg’s signature irreverent morning radio energy with the NFL kickoff, featuring a special football-themed edition of the “Guadalupe Squares”—the show’s long-running parody of Hollywood Squares. The cast delivers sharp satire, impersonations, and wild banter, blending football talk, celebrity impressions, and locals-only inside jokes.
Listeners get a comedic rundown of NFL, pop culture, and radio life as callers play for prizes.

Key Segments & Discussion Highlights

1. Football Is Back – NFL Season Vibes

[04:00]

• Excitement over NFL’s return animates the show
• Dick Toledo hypes his FanDuel bets and the schedule:

  “I'll take Caleb Williams at home to defeat the Vikings... Seattle Seahawks to defeat the 49ers... Houston upsetting the Rams, and Joe Burrow to get his first win of the season against Cleveland.”

• Humorous self-awareness about betting:

  “You can use your profit boost token however you'd like... to get into the NFL action with a chance to win even bigger.”

2. NFL-Themed Guadalupe Squares – Satirical Roleplay

[07:00]

• Squares include impersonations of:
  • Jerry Jones
  • OJ Simpson
  • President Trump
  • Bill Belichick + “Jordan”
  • Oxy’d-out Brady
  • Shannon Sharpe
  • Jeff Foxworthy
  • Patrick Mahomes (with “musical” bits)
  • Radio boss “Tripley”
• Structure: Each square’s character delivers monologues and interacts with contestants, riffing on football, their “persona,” and random absurdity.

A. Top Row Banter

Jerry Jones (Owner, Dallas Cowboys)
[08:00]

• On the Cowboys’ opening loss:

  “We were toe to toe with Philadelphia Eagles last night... CD Lamb grew alligator arms at the end of game. We lost the game.” (Jerry voice)

• Stereotypical “down-home” threats:

  “When I got home, I'm gonna punch your mama right in the mouth there, Stephen.”

• Self-deprecating:

  “Dallas Cowboys lost their first game. We got that out the way... 16 and 0 from here on out.”

OJ Simpson
[10:30]

• Jokes about his notoriety and fantasy football prowess:

  “I'm winning the fantasy football league down here in hell... Who gets hurt when OJ's around? Nobody.” “Only thing you break is records.” (OJ voice)

• Awkward allusions to his past...

  “Where were you back in 94? I needed you.”

President Trump
[13:00]

• Comments on recent (fictional) “military actions”:

  “Some people, Brady, some people out there calling it murder... They call it good business.”

• Football credentials:

  “I was a owner of a football team called the New Jersey Generals... Herschel Walker. Doug Flutie. It was real.” “And the whole team was shot to death by liberal Chicago politicians.” (Parodying both football and political hyperbole)

• Political jabs at Chicago/EU mayors and governors:

  “Big fat pricks. Is that his name? Governor Pricks? I believe that's it.”

B. Middle Row Madness

Bill Belichick (& Girlfriend Jordan)
[17:15]

• Parody of Belichick’s dour press persona, sparring with “Jordan”:

  “I lost the game on Monday, but I guarantee I got blown more than lost. Five times more than you guys did this week. Totally worth it to have a 20 year old girlfriend.”
  Jordan: “Do your job.”
  Belichick: “We're on to Indianapolis. All righty. Indianapolis is the nickname of my dick.”

• Jokes about solving ED with “20-year-olds".

Oxy Brady (Brady Bogen on painkillers)
[19:30]

• Stream-of-consciousness hallucinations:

  “I'm flying right now, Cory... It's like a ballerina on an unbalanced stage.” “Cory, did you know you're covered in tarantulas? The most beautiful thing I've ever seen.” “My balls are one foot. I'm looking at them right now. They're spreading across the floor like pancakes...”

• Sells the bit with mock confusion and delight.

Shannon Sharpe
[23:00]

• Energetic rapid-fire:

  “Club Shay Shay. Big fan club. Chase ain't gonna be on podcast today... Skip! Skip!”

  • Skewers the sports-shouting TV persona and his catchphrases.

C. Bottom Row & Celebrity Cameos

Jeff Foxworthy ("You might be a redneck...")
[26:20]

• Delivers classic setup:

  “If you cut your grass and you find a car—like that one. Thanks, Jeff.”

• Used to mark winning square.

Patrick Mahomes
[28:00]

• Prone to singing; riffs on his voice and image:

  “Patrick Mahomes taking on San Diego Chargers. Even though they're not in San Diego anymore...”
  [Sings] “I'm traveling down the road and flirting with disaster, Got the pedal to the floor...”

  • Hyper and outlandish, mashes singing with sports takes.

  “We're gonna be in super bowl again... Chiefs win tonight. Probably about 38 to 7.”

  • Parodies his family and coach (Andy Reid "Are you gonna finish those fries?").
  • Brazil jokes & a risqué punchline: “I'm going to have sex with a hot girl with a wiener. Oh, that's implied, right? It's Brazil.”

Tripley (Parody of "Triple" from the real station)
[31:45]

• Jokes about being "Lord and Savior" of the studio:

  “You're fired. Just kidding, Brady... Should you be driving? No, you just shouldn't be driving.”

3. Game Play – Callers Compete in Squares

[34:00]

• Callers Jim & Melissa join in; each picks squares, interacts with the characters, and answers humorous trivia—e.g.,
  • “Being lonely has a more damaging effect on your health than obesity.”

    Oxy Brady: "Oh, yeah…Being fat is not as detrimental as being Larry— I mean, lonely.”

  • “French school children were once allowed four glasses of wine per day.”

    Mahomes: “That's fine by me…I'll say yes. I'm turning to Ralphie by the second.”

• X vs. O progression, with jokes after each answer.
• Final zingers—Tripley:

  “Alcohol sales in the US account for almost 8% of our GDP.”

  • More redneck/finance jokes about "gross domestic product."

4. Meta Satire & Show Closer

[50:30]

• Jokes about local radio (Phoenix Rising soccer broadcast, “Soccer on the radio is a good band name”), trailing off with suggestions for new band names and veering into local charity shout-outs.
• Satirical “simulation is broken” commentary:

  “I told you earlier this week that it was completely broken. When I found out the guy running for governor in New Jersey’s name was Jack Schitterelli…and Bo ye poons doing weather…and now for sure. I know it's broken. Conor McGregor's running for president of Ireland…”

Notable Quotes & Moments (with Timestamps)

• Jerry Jones on the Cowboys loss:

  “Dallas Cowboys lost their first game. We got that out the way... 16 and 0 from here on out.” (08:30, Jerry)

• OJ Simpson on his “skills”:

  “I think Jerry Jones should trade for me. I think I'm as good as the guy they got. …Who gets hurt when OJ's around? Nobody.” (10:45, OJ)

• Trump on owning a football team:

  “I was a owner of a football team called the New Jersey Generals…Was it real? It was real. Spent a lot of money.” (13:25, Trump)

• Belichick on “winning”:

  “I guarantee I got blown more than lost. Five times more than you guys did this week.” (17:25, Belichick)

• Oxy Brady in full absurdity:

  “My balls are one foot. I'm looking at them. They're spreading across the floor like pancakes. Uh oh. The floor's hot lava. The floor's hot lava.” (19:55, Oxy Brady)

• Shannon Sharpe’s refrain:

  “Skip, Skip, skip, Skip. You can't skip. You can't skip. There's no way you can skip.” (23:30, Shannon Sharpe)

• Patrick Mahomes sings:

  “[Sings] I'm traveling down the road and flirting with disaster…” (28:05, Mahomes)

• Mahomes in Brazil punchline:

  “I'm going to have sex with a hot girl with a wiener. Oh, that's implied, right? It's Brazil.” (29:40, Mahomes)

• Show’s response to Arizona sports broadcasting:

  “Soccer on the radio is a good band name.” (52:10, Holmberg)

Tone & Takeaways

• The episode is high energy, zany, and unapologetically irreverent.
• Sports serve as the thread, but the jokes, parodies, and spontaneous riffing are the main attractions.
• Impressionist comedy and rapid-fire non-sequiturs bring the NFL opening weekend spirit to life, while the local flavor and off-color asides are classic HMS.
• Even if listeners are just tuning in for sports, they’ll quickly realize the Squares is equal parts roast, improv, and Arizona-centric sketch show.

Final Thoughts

This episode of “Guadalupe Squares” is a fast-moving comedy blitz, blending real NFL anticipation, local radio quirks, and absurdist impersonations.
Stand-out comedic set pieces include Oxy Brady’s hallucinations and Mahomes’ singing, but the cast’s commitment to each bit keeps every square buzzing—making it a great introduction to the rowdy world of Holmberg’s Morning Sickness.

[Note: advertisements, promotional plugs, and non-content segments were skipped in this summary.]