Podcast Summary: Holmberg's Morning Sickness — Frank Caliendo Joins In (12-15-25)

Overview

Main Theme:
Comedian and master impressionist Frank Caliendo visits the HMS studio for a wide-ranging, candid, and hilarious chat. The episode dives into the experience of being fired in show business, behind-the-scenes stories from TV and radio, a debrief of the wild recent "After Dark" live show, and honest commentary about Arizona Cardinals' ownership woes. The conversation is frank, brisk, and filled with comedic banter and impressions.

Key Discussion Points & Insights

1. The Art of Being Fired in Showbiz

• Frank’s Exit from Fox

  • Frank details how his contract at Fox was not renewed, and how he could sense the writing on the wall — especially compared to years prior when renewal was a sure thing.
  • “Each time before, when the contract was up, they were begging me… They weren’t begging me that time.” — Frank Caliendo [02:20]
  • Reflects on the pressure to keep recycling impressions: "They’d be like, ‘How about Andy Rooney?’ I’m like, ‘He died three weeks ago!’" — Frank Caliendo [02:45]

• Who Reaches Out After You’re Fired?

  • Frank shares that after leaving Fox, only Jay Glazer said anything; Terry Bradshaw and the others did not reach out.
  • "Terry's like, 'I don't even remember him. I think I have CTA...'" — Frank Caliendo (impersonating Bradshaw) [04:45]

• Transition to ESPN

  • Frank was never officially fired from ESPN, since he didn't want to stay: “I fired myself! ...You didn’t break up with me, I broke up with you.” — Frank Caliendo [06:35]
  • Comments on creative frustration at ESPN; how the best bits were "inside" jokes, which executives never seemed to appreciate.

• Holmberg’s Radio Firing Story

  • John shares his own story of being pre-warned about getting fired and deliberately pushing the envelope on-air to accelerate the process.
  • “We spent a minute and a half simulating fellatio on the air, trying to get fired earlier in the week.” — John Holmberg [09:27]
  • He was eventually rehired after the station realized their mistake.
  • Discussion about why radio studios never have locking doors — so no one can lock in after learning they’re being let go.

• General Reflection

  • Frank: “Everybody…eventually, 99.9% of the time, gets fired from something in this business.” [12:12]
  • Commentary on creative burnout, difficulties of pitching new ideas to executives who only want “what worked before,” and the value of having stand-up as a fallback.

2. Behind the Curtain: The ‘After Dark’ Live Show

• Debrief and Banter

  • The group recaps the wild Stand Up Live “After Dark” show: audience reactions, edgy content, and backstage antics with fellow comedians Jon Lovitz and Kato Kaelin.
  • Holmberg: "You did some stuff you would not normally have done." — [16:01]
  • Frank teases John for allegedly starting the night filthy: “Everything that came out of your mouth was filthy.” — Frank Caliendo [16:14]
  • Ongoing riff about a “vaginal mesh” joke and how some audience members reacted with shock.

• Audience and Backstage Energy

  • Descriptions of hardcore fans vs. newcomers and discomfort during certain video segments.
  • "There were people looking down at their foreheads, like 'Get me out!'" — Frank Caliendo [18:40]
  • Backstage, Lovitz feigns disinterest but is clearly engaged, "throwing popcorn in like the Bill Hader meme." [19:18]

• Celebrity Guests and On-stage Moments

  • Lovitz wanted his New Year's Eve plug before Frank's, out of ego.
  • Jay Pharaoh was originally slated; Lovitz as a 'backup guest' became the running gag of the night.
  • Cato Kaelin’s willingness to take all jokes, except about O.J. — “When you do the O.J., every time, he’s like, it is just… eerily…” — Frank Caliendo [23:47]

• Impression Showcases

  • Frank and John riff several impressions, from John Madden to O.J. Simpson and Donald Trump throughout.
  • Memorable moment: post-show audience saying, "When Clinton blew Trump, we were dying!" — John Holmberg [25:33]

• Chris Turner’s Freestyle Rap

  • The praise for British comic Chris Turner’s improv rap set closes out the segment.
  • "That guy is brilliant… called you Brody, which was funny." — Frank Caliendo [26:08]

3. Arizona Cardinals Ownership & Team Woes

• Blunt Assessment

  • Holmberg seeds a fiery sports talk segment: "Assess the Cardinals. What would you do if you were GM?"
  • Frank’s satirical take: "Offer to retire. It doesn’t look good." — Frank Caliendo [26:53]
  • Kyler Murray's contract and future discussed — "They gotta pay $30 million just..." [27:04]

• Ownership Problems

  • Discussion lands squarely on team owner Michael Bidwill: "Isn’t the revamping Bidwell? He has to leave, right?" — John Holmberg [27:15]
  • Frank’s Trump/Jerry Jones impression: “I will be here for eternity and plus one.” [27:48]
  • Holmberg: "The one thing synonymous with Cardinal failure is the name Bidwell." [30:01]
  • Family-owned NFL team failures compared: Raiders (Mark Davis) and Colts (Irsay).

• Billionaire Psychology

  • Discussion on how billionaires-turned-team-owners become isolated from honest feedback.
  • Frank shares an anecdote from a Trump Tower taping. Trump, frustrated, asks: “Was that good?” and only receives sycophantic praise.
  • Caliendo: “[Trump said] No, Frank, that’s part of the problem. I can’t get real answers.” [32:57]

4. Neighborhood Life & Homeowners’ Associations (HOAs)

• HOA Anecdotes

  • Frank’s wife is now the HOA president; stories of former “dictator” HOA president leaving passive-aggressive notes.
  • Frank: "Does anyone ever tell her she's not great? I do and it gets me in trouble." [34:26]
  • Amusing debate about paint colors, privacy vs. security gates, and neighbors’ opinions.
  • John: "Paint your house whatever color you want. Just don't paint my house." [35:45]

• The Value (and Annoyance) of HOAs

  • Jokes about HOAs working like the mafia—"That's a very nice way to put it." — Frank Caliendo [40:34]
  • John aspires to "dismantle" the HOA and make personal responsibility more important.
  • Frank: "It's a dream. Won't happen." [41:14]

Notable & Memorable Quotes

• "Everybody…eventually, 99.9% of the time, gets fired from something in this business."
  — Frank Caliendo [12:12]

• “We spent a minute and a half simulating fellatio on the air, trying to get fired earlier in the week.”
  — John Holmberg [09:27]

• "Each time before, when the contract was up, they were begging me… They weren’t begging me that time."
  — Frank Caliendo (about Fox) [02:20]

• "Terry's like, 'I don't even remember him. I think I have CTA...'"
  — Frank Caliendo (as Terry Bradshaw) [04:45]

• "I fired myself! ...You didn’t break up with me, I broke up with you."
  — Frank Caliendo (on ESPN) [06:35]

• "Does anyone ever tell her she's not great? I do and it gets me in trouble."
  — Frank Caliendo (about his wife, the HOA president) [34:26]

• "Isn’t the revamping Bidwell? He has to leave, right?"
  — John Holmberg [27:15]

• "I will be here for eternity and plus one."
  — Frank Caliendo (as Jerry Jones/Trump parody) [27:48]

• "No, Frank, that’s part of the problem. I can’t get real answers."
  — Frank Caliendo quoting Donald Trump [32:57]

Timestamps for Important Segments

• [01:34] — Frank arrives, conversation starts
• [02:09-04:25] — Frank describes Fox firing, pressure to repeat impressions
• [06:15-08:05] — ESPN exit and creative differences
• [09:27-11:25] — Holmberg's notorious radio firing stunt
• [12:12-13:21] — Reflections on being fired in entertainment
• [16:01-21:00] — After Dark show debrief, on-stage/green room antics, Lovitz and Kato Kaelin
• [25:33-26:08] — Clinton-Trump sketch, Chris Turner’s improv rap
• [26:42-32:05] — Cardinals as a franchise, ownership failings, and billionaire egos
• [32:24-33:03] — Trump Tower story: candor and sycophants in power
• [33:55-36:44] — Presidential ego and HOA anecdotes
• [40:32-41:14] — Jokes about HOAs, mafia comparisons, neighborhood politics

Tone & Language

• The conversation is riffing, irreverent, and peppered with impressions.
• The mood bounces between self-deprecating honesty (about career lows) and sharply funny mockery (of celebrity egos, corporate leadership, sports owners, and petty neighbor squabbles).
• Interactions are collegial, with running in-jokes and mutual roasting among Frank, John, and frequent appearances by celebrity “voices.”

For Listeners Who Missed the Episode

If you didn’t catch this episode, you missed a tour through the highs and lows of comedic careers, a raucous and revealing behind-the-curtain look at live radio and stage shows, and unfiltered opinions about ownership in professional sports. Frank Caliendo shines as always with spot-on impressions and open talk about the realities of show business (and homeowners’ associations!). The banter is lightning fast, and the laughs—and insight—are nonstop.

For specific impressions, comedic bits, or insider stories, check timestamps above to jump right in.