Podcast Summary: Holmberg's Morning Sickness (98KUPD)

Episode: 09-25-25 - Eric D'Allesandro - Stand Up Live - In Studio

Date: September 25, 2025
Host: John Holmberg (with Brady Bogen & Brad Vesely)
Guest: Eric D’Alessandro (Comedian)

Overview

This episode features comedian Eric D’Alessandro, in Phoenix for a one-night show at Stand Up Live. The conversation is a lively, often hilarious mix touching on topics like appearances (especially hair), comedy audiences, generational and technological shifts, the impact of social media on entertainment, and the future of community and content creation. The tone is irreverent, spontaneous, and filled with playful banter.

Key Discussion Points & Insights

1. Hair, Identity, and the Man Bun Stigma

[00:38 - 03:46]

• The gang pokes fun at Eric’s Italian surname and promotional photo with a man bun, launching a running discussion about hair as a key part of one’s persona.
• Eric: “The man bun gets a bad reputation from the people who have stolen it…like, who you picturing with a man bun? A guy with smelling salts, or Crossfit…that’s not me. I’m a douchebag from Staten Island.” [00:48]
• Holmberg jokes about his own baldness and the social perceptions linked to hair (or lack thereof).
• Memorable Comparison: “What would Uncle Jesse do without his hair? It’s part of his whole identity.” – Eric [03:37]

2. Comedians & Their Audiences

[05:09 - 10:24]

• Discussion on the diversity of Eric’s audience—from young dating couples to grandmas, and notably, a strong gay following.
• Eric: “Anyone? Man, I think every comedian believes they can play any room….I’ve had to win over every crowd.” [05:33]
• Both joke about how gay men are often more complimentary than women.
• Holmberg: “A woman has never told me she’d give me her car if I called her ‘daddy’—but I’ve had a gay guy do it. It’s an awesome feeling, right?” [06:13]
• On tricky crowds, Eric says the worst is actually a small audience: “If there’s seven people in there…feels like a focus group, it feels stupid.” [10:01]
• Holmberg counters that the hardest is a room full of country music fans: “That is a horrible, awful…if you walk out there and you see hats—get him out. You won’t even understand what you’re saying.” [10:24]

3. Technology & Cultural Change

[14:04 - 22:26]

• Segue to AI anxiety—Eric admits: “I can’t sleep at night…I love human stories. We’re already seeing movies disappear. I want movies to make a comeback. I feel like they’re not culturally relevant anymore.” [14:15]
• The group laments how the reference points in pop culture are all at least 20 years old: “Anything we talk about as a cliché or a wink and a smile, that’s all stuff from 30 years ago. We don’t have any references as of late.” – Eric [14:52]
• On generational sameness: “I’m wearing the same sneakers and hat as a 17-year-old. My father wore orthopedic shoes. Now, 40-year-olds dress the same as their 10-year-old.” – Eric [15:03]
• Jokes about language policing on-air vs. uncensored internet—Holmberg notes, “That’s why radio is gonna die. We’re still playing these games from 1950.” [16:04]
• Holmberg recounts a surreal new tech experience: drones at events directing people to Uber pickups. “That’s really Jetsons.” – Eric [17:14]
• They marvel at driverless cars and the pace of change, “We don’t even bat an eye that there are driverless cars now.” – Eric [17:29]

4. Society Splintered: Community, Loneliness & E-commerce

[20:10 - 26:30]

• Eric, now a new father, worries about recreating experiences for his son: “The world I wanted to recreate for him doesn’t exist anymore… malls, movie rentals, even community is gone. No more stores—everything eviscerated.” [20:12]
• On delivery and non-contact culture: “We got so efficient…when I’d order something as a kid, it’d take three weeks. Now, an hour.” – Eric [25:51]
• Holmberg admits: “Sometimes I don’t even want to get up off the couch to see if I have the thing I want…I just order it.” [25:56]

5. Aging & Demographics

[26:56 - 29:39]

• Spirited, tongue-in-cheek debate about living longer: “You want to live to a hundred? I call them resource suckers.” – Holmberg [27:08]
• Eric: “How grandmas have changed—used to look like Bea Arthur, now they look like Susan Sarandon…Life expectancy is going to be so wild.” [27:33]
• Lighthearted brainstorming (morbidly) about fixing longevity: “We start killing them…Bill Burr said the best way to do it is to just start sinking cruise ships.” – Eric [28:34]

6. The Rise (and Problems) of Content Creation

[29:42 - 34:25]

• Eric predicts a renewed craving for communal experiences. “We’re lonelier than ever, sadder than ever, more depressed—and it’s because we’re not with each other.” [29:49]
• Harsh critique of influencer/“content creation” culture: “TikTok and Facebook are selling you back the idea of what they stole…They’re giving you a little taste of humanity because that’s what they took.” – Eric [31:01]
• Holmberg and Eric agree that anyone can perform online now, but gatekeepers in entertainment used to keep standards. “I think gatekeepers were a good thing.” – Eric [33:39]
• On the content treadmill: “Being a content creator is jail…it’s miserable. The audience is not what you think it is. TikTok, Instagram, it’s not who you follow. It’s random things. I don’t want to see my cousin golfing in Scottsdale if I can see this Dodge Durango drive through a restaurant.” [32:07]
• Discussion closes with the idea that viral views are the new “Apollo Sandman sweep”—if people don’t like your stuff, it just disappears.

Notable Quotes & Moments (With Timestamps)

• “The man bun gets a bad reputation from the people who have stolen it—you’re picturing a guy with smelling salts or Crossfit. That’s not me. I’m a douchebag from Staten Island.”
  — Eric D’Alessandro [00:48]

• “A woman has never told me she’d give me her car if I called her ‘daddy’—but I’ve had a gay guy do it. It’s an awesome feeling, right?”
  — Holmberg [06:13]

• “If this doesn’t work out over here, I have options…There’s always the B league.”
  — Holmberg, on being hit on by gay men [07:56]

• “If there’s seven people in there…it feels like a focus group, it feels stupid.”
  — Eric [10:01]

• “That’s why radio is gonna die. We’re still playing these games from 1950.”
  — Holmberg [16:04]

• “I’m wearing the same sneakers and hat as a 17-year-old. My father wore orthopedic shoes.”
  — Eric [15:03]

• “TikTok and Facebook are selling you back the idea of what they stole from you.”
  — Eric [31:01]

• “Being a content creator is jail…it’s miserable, it’s terrible, it’s not good.”
  — Eric [32:07]

• “I think gatekeepers were a good thing.”
  — Eric [33:39]

Timestamps for Important Segments

• 00:38 — Eric & Holmberg riff on the man bun and hair identity
• 05:09 — Who is Eric’s audience? Comedy crowd diversity
• 10:01 — Which audiences are hardest for comics?
• 14:04 — AI, media, and cultural reference points disappearing
• 15:03 — Flattening of generational differences in culture
• 20:10 — Parenting in a changing, disconnected society
• 25:53 — E-commerce and the death of physical stores
• 26:56 — Joking about longevity and the burdens of old age
• 29:42 — “What needs to change?” Eric’s vision for renewed community
• 31:01-33:46 — Deep dive on content creation, social media, and gatekeeping
• 34:17 — The “Sandman” sweep for bad internet content

Conclusion

This episode is a fast-paced, comic but thoughtful look at the ways technology, culture, and comedy have shifted, featuring playful attacks on social stereotypes and a serious undercurrent of concern for society’s trajectory. Eric D’Alessandro blends candid confessions with sharp social commentary, riffing on what it’s like to perform in a world that’s increasingly distracted, disjointed, and digital—and why we may crave a return to face-to-face community more than ever.