Podcast Summary: Holmberg's Morning Sickness – Entertainment Drill with Dale Hellestrae
Date: October 30, 2025
Episode: 10-30-25 – Entertainment Drill – THU – w/Dale Hellestrae – Dorothy Will Not Be Seen In The Wicked Sequel
Host: John Holmberg with Brady Bogen, Bret Vesely, Dick Toledo, and guest Dale Hellestrae
Episode Overview
Today’s episode centers around the “Entertainment Drill,” a rapid-fire discussion of quirky entertainment news and pop culture, with plenty of playful back-and-forth. Regular hosts John Holmberg, Brady Bogen, Bret Vesely, and Dick Toledo are joined by former NFL player Dale Hellestrae, who brings his trademark dry wit to the table. The team discusses everything from Arnold Schwarzenegger’s surprise billionaire status to odd Peloton classes, the new "Wicked" movie’s Dorothy problem, Toy Story 5 rumors, and general theater talk. As always, lighthearted tangents and jokes abound.
Key Discussion Points & Insights
1. Celebrity Athleticism (01:51–02:30)
- John and Dale discuss Kevin Ray’s (Suns announcer) athletic ability.
- Basketball: "He's pretty good at basketball. Yeah. He looked natural doing that." (A, 02:20)
- Fighting/Golf: "Golf was the weirdest one. Fighting is pretty good. It's just awkward." (A, 02:06)
- Banter about Al McCoy’s legendary “shazam” calls.
2. Arnold Schwarzenegger Joins the Billionaires Club (02:53–03:43)
- Arnold’s net worth is now $1.2 billion, thanks to smart investments with Dimensional Fund Advisors and stakes in real estate and hotels.
- “Nice job, Arnold.” (A, 03:00)
- "He also owns a piece of Easton Town Center in Columbus, Ohio... he's got some equity in Waldorf Astoria Hotel in Los Angeles." (E, 03:16–03:43)
- Jokingly called “solid investor, actor, and politician.” (A, 03:43)
3. Spooky Season on Peloton (03:50–04:22)
- Halloween-themed “Friday the 13th” Peloton classes, where riders “pedal to survive” Jason Voorhees.
- “There are three official Friday the 13th themed classes... users pedal to survive Jason Voorhees.” (E, 04:01)
- “The instructors will be dressed up like camp counselors.” (E, 04:22)
4. “Wicked” Sequel Will Not Show Dorothy’s Face (04:28–06:05)
- Director Jon M. Chu has chosen never to show Dorothy’s face in the new film, to avoid stepping on audience perception.
- “I don't want to step on who you think Dorothy is... The movie is still Elphaba and Glinda's journey.” (D, quoting Chu, 04:51)
- Playful confusion on how to pronounce “Elphaba.”
- Dale tries: “Not E, L, P, H, A, B, A. Huh?” (D, 05:16)
- “You didn't see Wicked.” “I did not see Wicked. Why?” (A & D, 06:03–06:05)
5. Theatre Experiences and Childhood Crushes (06:06–07:37)
- Dale admits he hasn’t seen “Wicked,” but has seen "Grease" and "42nd Street" in London.
- Light teasing about seeing “Grease” with British accents.
- "Did Grease have accents? Were they British? … No, it was. It seemed like there's John Travolta." (A & D, 06:55–07:07)
- Childhood pop star crushes, including Bow Wow Wow’s singer, who “looks good for 58.”
- “She looks pretty good for 58. Singer looks pretty good—I mean, for 58.” (A, 07:23–07:29)
6. Toy Story 5 – Cast Away Parody? (07:53–08:37)
- Tim Allen jokes about Toy Story 5 featuring a FedEx plane crash with 100 Buzz Lightyear dolls on an island (a la "Cast Away").
- ”It’s Cast Away with Lightyear. That's hilarious.” (A, 08:07)
- Allen would voice all the different Buzzes. "He does multiple voices of the Buzzes that are trapped on the island." (E, 08:14)
- Discussion quickly threads into franchise fatigue and the value of sequels.
7. Humorous Take on Movie Franchises & Streaming Confusion (08:32–09:47)
- Dale and John chuckle about horror franchises and redundant sequels.
- "It's like Halloween 12. Come on. I see somebody get killed. It's scary... Why am I going to waste two hours?" (D, 08:39)
- Jabs about Dale’s difficulty using apps and moving money through technology.
- “I can't get my money that he paid me through the Apple app.” (D, 09:30)
- “You could probably counterfeit $33 faster than figure this out.” (A, 09:51)
Notable Quotes & Memorable Moments
-
On Arnold’s Success:
“Solid investor and actor and politician. That's pretty good. Follow Arnold's advice.”
– John Holmberg (03:43) -
On Avoiding Dorothy’s Face in ‘Wicked’:
“I don't want to step on who you think Dorothy is... the movie is still Elphaba and Glinda’s journey.”
– Dale Hellestrae quoting Jon M. Chu (Director) (04:51) -
On Pop Star Aging:
“She looks pretty good for 58. Singer look pretty good—I mean, for 58.”
– John Holmberg (07:23) -
Toy Story 5 Pitch:
“It’s Cast Away with Lightyear. That's hilarious.”
– John Holmberg (08:07) -
On Franchise Fatigue:
“It's like Halloween 12. Come on. I see somebody get killed. It's scary... Why am I going to waste two hours?”
– Dale Hellestrae (08:39) -
On Using Technology:
“You could probably counterfeit $33 faster than figure this out.”
– John Holmberg (09:51)
Timestamps for Important Segments
- 00:00–01:12: Opening ads & show intro (skipped)
- 01:51–02:30: Kevin Ray’s sports skills
- 02:53–03:43: Arnold Schwarzenegger joins the billionaires club
- 03:50–04:22: Peloton’s horror-themed classes for Halloween
- 04:28–06:05: “Wicked” sequel to keep Dorothy’s face hidden
- 06:06–07:37: Theater stories, “Grease” in London, pop star crushes
- 07:53–08:37: Tim Allen’s Toy Story 5 “Cast Away” idea
- 08:32–09:47: Movie sequel fatigue, app/technology troubles
Tone & Style
This episode is infused with the hosts’ characteristic sarcasm, camaraderie, and quick banter. The tone is fun, irreverent, and sometimes self-deprecating, with everyone willing to poke fun at themselves and each other. Dale Hellestrae’s inclusion brings a deadpan foil to John Holmberg’s rapid-fire hosting.
Summary for New Listeners
If you missed this episode, you missed a lively, joke-filled riff on everything from celebrity fortunes to musical theater, horror movie cliches, and the hilarious complications of modern technology. The magic of HMS is in the effortless chemistry between host and guests, making even brief entertainment news a laugh-out-loud experience.