Podcast Summary: Holmberg’s Morning Sickness - Guad Squares w/ Jonathan Kite

Podcast: Holmberg’s Morning Sickness (HMS), 98KUPD
Episode Date: September 26, 2025
Special Guest: Jonathan Kite (Impressionist, Comedian)
Theme: The Guad Squares – A Comedy Tic-Tac-Toe with Star Impressions

Episode Overview

This episode of Holmberg’s Morning Sickness features the comedic talents of Jonathan Kite, known for his vast repertoire of celebrity impressions. The show centers around the recurring segment "Guad Squares," where guests play Tic-Tac-Toe as various celebrity personalities. Jonathan Kite fills the squares with a laugh-out-loud sequence of rapid-fire, razor-sharp impressions—including Anthony Bourdain, Mickey Rourke, Donald Trump, Mike Lindell, Pythagoras as Brady, Tom Hanks, Tom and Beau Bridges, and more. The tone is energetic, chaotic, and hilarious, providing listeners with a blend of improvisational games and ribbing commentary on pop culture, personalities, and current events.

Key Discussion Points & Highlights

1. Jonathan Kite's Comic Takeover

• The show revolves around Kite's impressions, allowing him to showcase new voices and riff dynamically with the HMS crew (John Holmberg, Brady Bogen, Bret Vesely, Dick Toledo).
• Holmberg immediately highlights Kite's current shows at Desert Ridge Improv, setting a playful, self-promotional mood.

2. Guad Squares – Celebrity Squares Comedy Game

• The segment begins (03:15), with each "square" featuring Kite in character, bantering with hosts and one another.
• Each impression includes quick-witted barbs, inside jokes, and satirical commentary on their persona or recent pop culture moments.

Notable Impressions:

• Anthony Bourdain (03:50)
  • Laid-back, existential humor: “I’ve never been better out here in the cool Arizona sun, as I sit back with tequila and hang out with the saguaro.”
• Mickey Rourke as grilled by "Piers Morgan" (05:10):
  • Salty, self-deprecating takes: “I used my speech at the SAG Award to shame Hollywood for not hiring Eric Roberts...”
  • On new actors: “Lewis is not a great actor. No. I don't care for anybody. The guys who came before me, you know, Harvey Keitel, Christopher Walken, those kind of guys. Not these new guys...”
• Donald Trump (07:00)
  • Signature bravado: “Unbelievable. So great today. Absolutely fantastic. Been a busy week. I played a lot of golf. Nothing really happened in the news, so I was playing a lot of golf. You got Ryder Cup going on too? I got a lot of things going on. Apparently, I'm selling merch now in the White House for 2028... I've never run a day in my life. Not even on a treadmill.”
• Mike Lindell (08:10)
  • Pillow peddler delirium: “Let me just say we're offering a special this weekend, okay? If you buy a pillow, I'll come and sleep on it for you. I need a place to stay. My wife kicked me out.”
• Pythagoras Brady: (09:03)
  • Math confusion humor: “Yeah, I was doing some math earlier... 87 out of 100, what's the percentage of that? Can't quite do 87%. I'd have to look into that. I have an Asian friend I'm gonna ask later...”
• Tom Hanks (10:04)
  • Deadpan, conspiracy-tinged bit: "I am not here to play this game. I am here to say release the Epstein files. Because I am the only name people associate with... Got a story. And I am telling you, I was not there. And I'm saying, come on guys, just release the file."
• Jeff & Beau Bridges (12:00)
  • Fraternal, laid-back vibe: "Hey, man. We're here to tell you we're doing the Fabulous Baker Boys 2... People don't know this, man. He was my stuntman in Starman, man..."

3. Show Banter & Technical Difficulties

• The show is punctuated by running jokes about studio equipment: malfunctioning phones, internet, and tongue-in-cheek references to “Tylenol as a cure” for everything (13:37).
  • Tripp Reeb: "You can guzzle as much Tylenol as you want as long as you’re not pregnant… Despite the gut I wear… this is all pure bucket of chicken."
• The crew riffs on how the show’s phones keep dying due to call volume, likening it to "phones from the Biden administration—Sleepy Joe!"

4. Improv Game – Audience Participation

• (19:20) One caller, David, gets through as others are booted off due to phone issues.
• A sample "Squares" trivia question:
  • Is it true or false that all-natural diamonds are at least 525 million years old?
  • Bourdain (Kite): Delivers a poetic, tangential answer and says “That is false.”
  • David agrees—it's correct, and he wins tickets.

5. Behind-the-Scenes and Impressions Workshop

• After the game, the discussion pivots to Kite's approach to impressions and bits he’s working on, including new Vince Vaughn and RFK Jr. voices (24:12).
  • On Vince Vaughn: “I’m trying to bring the energy right now, you know what I’m saying, like it’s kinda early in the day for Vinny boy... Daddy’s up right now.”
  • On RFK Jr.: “He always sounds like he’s deep-throating a vibrator. His campaign slogan was ‘I’m coming.’”
• The hosts praise Kite’s Bourdain: “My favorite thing with your Bourdain is the thousand-yard gaze... he was just staring off into the hallway.”

Memorable Quotes & Moments

• Mickey Rourke (as Kite, 05:55):
  "The new guys, they’re not the real guys. They’re not like Harvey Keitel, Christopher Walken. They’re the guys. Not these new guys. They’re not the real guys."
• Mike Lindell (08:21):
  "If you buy a pillow, I’ll come and sleep on it for you. I need a place to stay. My wife kicked me out."
• Tom Hanks (10:10):
  "I am here to say release the Epstein files. Because I am the only name people associate with... And I am telling you, I was not there."
• RFK Jr. (Jonathan Kite, 24:40):
  “He always sounds like he’s deep-throating a vibrator. His campaign slogan was ‘I’m coming’... He sounds like he has AT&T service.”

Timestamps for Major Segments

• 03:15 — "Jonathan Kite Squares" segment begins
• 03:50 — Anthony Bourdain impression
• 05:10 — Piers Morgan interviews Mickey Rourke (Kite)
• 07:00 — Trump impression
• 08:10 — Mike Lindell impression
• 09:03 — Pythagoras Brady
• 10:04 — Tom Hanks "Epstein Files" bit
• 12:00 — Jeff & Beau Bridges impressions
• 13:37 — Tylenol jokes and technical difficulties
• 19:20 — Listener call-in game with David
• 24:12 — Jonathan Kite discusses new impressions (Vince Vaughn, RFK Jr.)

Summary & Takeaways

• This episode serves as both a showcase for Jonathan Kite’s uncanny impressions and a meta-commentary on the absurdities of celebrity culture.
• Kite’s improvisational prowess fuels relentless joke density, lampooning celebrities and the HMS crew with affectionate irreverence.
• Fans of comedy and impressions will appreciate the high energy, fast gags, and inside-show references. Even with the technical hiccups, the laughter is non-stop, with plenty of quotable lines for fans to repeat.

Best for: Comedy fans, particularly those who enjoy sharp celebrity satire, radio improv, and pop culture roasts.

Listen for: Jonathan Kite’s evolving impressions, quick banter with the hosts, and over-the-top game show madness that manages to lampoon both pop culture and radio itself.