Holmberg's Morning Sickness – Entertainment Drill with Frank Caliendo

Air Date: August 22, 2025
Featured Guest: Frank Caliendo
Main Hosts: Brady Bogen, Brett Vesely, John Holmberg, Dick Toledo

Episode Overview

This episode of "Holmberg’s Morning Sickness" centers on a visit from renowned comedian and impressionist Frank Caliendo. The gang dives into Frank’s upcoming shows at Desert Ridge Improv, brainstorms new comedy ideas, riffs on TV and streaming culture, invents ridiculous entertainment concepts, and provides a loose, laughter-filled take on the latest entertainment news. Throughout, the crew’s banter with Frank offers plenty of improvisation, impressions, and comedic tangents.

Key Discussion Points & Highlights

Frank Caliendo’s Upcoming Shows and Special Guests

• Frank’s Show Details
  • Performing at Desert Ridge Improv: Friday (one show at 6:30pm), Saturday (two shows at 6:00pm and 8:30pm)
  • Notable attendees include ex-NFL player Dale Hellestra, Suns announcer John Bloom, and potentially Kevin Ray.
  • Frank jokes about avoiding certain audience members and riffing live with play-by-play sports announcers.
• Possible Show Bits
  • The crew suggests Frank develop a “halftime show” bit during his act (03:04).

    “That’s actually a good bit for you anyway, is to just say, I don’t know how you... Let’s go down to the sidelines…” – Brady (03:08)

  • Frank contemplates making it a football-themed sketch, doing his Fox impressions and playing with broadcast tropes.

Frank’s Sleep Habits and John Gruden Stories

• Comedian Life
  • Frank confesses he wakes up at 4:30am for “no reason,” referencing the bizarre schedules of comedians and hosts.

    “I gotta get up at 5, 4:30am for no reason.” – Frank (04:30)

  • Shares an anecdote about John Gruden seeing his Tampa show, but leaving early to stick to his 6pm bedtime (05:02).

    “He gets up at 3:30am every morning, man... I get up at 3:30am every morning, man. I’m like, what time do you go to bed? 6pm.” – Frank, as John Gruden (04:49 to 05:03)

Entertainment Drill: Industry Riffs and News

• Apple TV+ Price Hike

  • Apple TV+ is raising its monthly fee by 30% (from $9.99 to $12.99) for existing customers within 30 days.

    “It’s reasonable for 12 bucks to get all that stuff.” – Brady (08:56)

  • Discussion on the spiraling cost of cord-cutting, a la carte streaming, and nostalgia for cable simplicity.

    “It’s like more like getting a limo instead of taking the bus.” – Frank (09:45) "DirecTV gave you all you wanted... now my TV bill is four, five hundred dollars a month at this point." – Brady (09:07)

• Netflix’s Astrological Recommendations

  • Netflix will suggest movies and shows based on users’ astrological signs, met with mockery.

    “This is the dumbest thing I’ve ever heard.” – Brady (10:52)

• True Detective Casting Rumors

  • Nicolas Cage is rumored for season 5, prompting the crew to riff on "John Maddenlock" and “Face/Off” reunion scenarios.

    "Yes. After I play John Madden, I'm gonna solve... called Maddenlock." – Frank (11:26) "It just seems like we're missing a clue of something. We should be doing something else, don’t you think? Not Nicolas Cage." – Brady (12:23)

• Little Nas X Heads Outfitted Meltdown

  • Little Nas X, reportedly seen in underwear and cowboy boots walking down the street after a party incident.

    “To recognize a celebrity in the middle of the street, losing his mind would be the greatest thing ever.” – Brady (13:38)

Comedy Brainstorm: Body Swap Movie Pitches

• “Tracy Friday” – The Ultimate Impressions Movie

  • The crew invents a movie where Frank is kicked in the head by Tracy Morgan and stuck speaking as Tracy, but can do all his impressions (“Tracy Friday”).

    “It’s called Tracy Friday instead of Freaky Friday, it’s Tracy Friday.” – Frank (16:18)

  • The plot snowballs: Tracy Morgan must kick Frank again to reverse the swap; after a car accident, Tracy loses use of his legs.

    “And you had to live your life like that.” – Brady (15:28) “I built a DeLorean to get your voice back, Frank. We gotta hurry back to the Frank future.” – Frank (18:37)

• Meta-Hollywood Spoofs

  • Discussing movie tropes, celebrity mishaps, and riffing on how these ideas would outdo sequels like Happy Gilmore 2.

Memorable Moments & Quotes

• On Early Bedtimes and Old-School Habits
  “You go to bed when the sun’s still up in the summer.” – Brady (05:36)

• On Streaming Cost Creeps
  “My bill for TV is in. Yours probably is crazy. You’ve got all your stuff… it’s like 4, $500 a month at this point.” – Brady (09:07)
  “To complain about cable prices going up and everything is in the same place.” – Frank (09:22)

• On Netflix’s Astrology Recommendations
  “This is the dumbest thing I’ve ever heard.” – Brady (10:52)

• On “John Maddenlock” as a Detective Character
  "After I play John Madden, I'm gonna have to solve... I'm gonna be called Maddenlock." – Frank (11:26)
  “And boom, the old lady crunched him.” – Frank, as Madden (11:46)

• On Spotting Little Nas X on the Street
  “To recognize a celebrity in the middle of the street, losing his mind, would be the greatest thing ever.” – Brady (13:38)

• On Swapping Voices with Tracy Morgan
  “I swear, Michelle, this is real. I can’t get out of it, but this is still the real Frank and stuff.” – Frank (15:43)
  “It’s called Tracy Friday instead of Freaky Friday, it’s Tracy Friday.” – Frank (16:18)

Timestamps for Important Segments

• Frank’s Show Information and Sports Crowd Plans: 01:51–04:20
• Comedy Brainstorm: Play-by-play Halftime & New Show Bits: 02:47–04:07
• Frank and Brady on Waking Early / Gruden Anecdote: 04:25–05:39
• Entertainment Drill & Apple TV+ Price Increase: 08:45–09:45
• Mocking Netflix’s Astro-Recs: 10:25–10:59
• True Detective/Nicolas Cage Riffs: 11:21–12:22
• Little Nas X Street Meltdown / Spotting a Celebrity: 13:06–14:52
• Body-Swap Movie Brainstorm – “Tracy Friday”: 15:13–18:37

Tone and Style

The episode’s tone is irreverent, fast-paced, and heavily reliant on quick-fire banter and comedic improv. Frank Caliendo’s fluid impressions boost the absurdity, while the hosts pile on suggestions, movie pitches, and take playful shots at streaming and entertainment culture.

Conclusion

This episode serves as a perfect showcase of the “HMS” signature blend of local Arizona color, showbiz lampooning, and zany, off-the-cuff comedic invention. With Frank Caliendo at their side, the crew veers from legitimate entertainment news to wildly creative brainstorming, offering plenty for fans of pop culture satire and classic radio camaraderie.