The Nateland Podcast #266: "The Generations" ft. Ryan Hamilton

Date: August 20, 2025
Hosts: Nate Bargatze, Brian Bates, Aaron Weber, Dusty Slay
Guest: Ryan Hamilton

Episode Overview

This episode is all about generational divides, nostalgia, and how our experiences shape who we are. The crew welcomes comedian Ryan Hamilton as they discuss the origins and stereotypes of different American generations, reminisce about their childhoods in the context of rapidly changing technology, share road stories, and debate the best (and worst) ways to leave your mark as a comic. The conversation is equal parts insightful and hilarious, packed with personal anecdotes, spirited teasing, and a deep dive into what it means to be a part of a "generation".

Key Discussion Points & Insights

1. Ryan Hamilton Joins: Comedy, Specials, and Suits

• Ryan is taping his first Netflix special at the Neptune Theater in Seattle on October 4th – a milestone for both him and the Nateland crew.
• The group discusses the growing size and professionalism of modern comedy shows, which has led Nate and Ryan to start wearing suits on stage.
• The pros and cons of wearing a suit: confidence, professionalism, performance impact, and a comedic anecdote about Jerry Seinfeld calling club comic attire “raking leaves jackets.”
  • Ryan quoting Seinfeld on Nate’s fans:
    • “Nate’s shows are amazing, these guys out there – they’re all wearing their raking leaves jackets.” (16:10)

2. On The Road: Stories from Gigs and Travel Dangers

• Brian shares the saga of his adopted dog Philly, training mishaps, and plans to have her as a road dog. The group jokes about dogs (and comics) all probably having "worms" from being on the road.
• The hosts each recount recent gigs, from Brian’s first pitches at baseball games in Jacksonville to corporate shows in Salina, Kansas (Brian’s “Salina’s favorite comic”), Dusty’s adventures in Cracker Barrel and Boot Barn corporate gigs, and rough travel memories—including sketchy hotels and the club comedian condo horror stories.

3. Comedy Club “Wall of Fame”: Who Gets to Sign It?

• The group debates the value and protocol of signing club walls—who is worthy, whether open mic’ers should count, and whether every club should have templates or criteria.
  • “Maybe you should have to headline… some people write their whole… they’ll cover up the whole…” (30:31)

4. Generational Definitions and Stereotypes

a. Naming the Generations (63:05+)

• Tom Brokaw’s book "The Greatest Generation" is credited for coining the term.
• The hosts riff on how generations get named ("Lost," "Greatest," "Silent," etc.), noting the arbitrariness:
  • Ryan: “And who–where does Tom Brokaw get off?” (63:32)
  • Dusty: "If you know who Tom Brokaw is, it's a real room divider. Because nobody knows, or you really know." (64:00)
• The progression discussed is:
  • Lost Generation (WWI)
  • Greatest Generation (WWII)
  • Silent Generation
  • Baby Boomers
  • Generation X
  • Millennials
  • Generation Z
  • Generation Alpha
  • Generation Beta (2025+)

b. What Makes a Generation?

• Much of it is hindsight: generations are labeled later by pop culture, books, or demographers; there's no formal body that decides.
• Early generations weren’t aware of being one:
  • Ryan: "I don't remember being called Generation X until we were like grown... Now we're labeling them before they're even born." (103:08)

c. Experience of Change Across Generations

• Discussion about which generation saw the most change:
  • Technological leaps: from horses to planes, black-and-white to color TV, to handheld devices.
  • The acceleration since the 2000s: "It feels like yesterday I bought a flip phone…" (96:58)
  • The 'Lucky Ones': born on the analog-digital cusp — "Oregon Trail Generation" or "Xennials."
    • Nate: "We got to experience the old school way and the new school way… real memories in both." (87:16)
    • Aaron: "They're benefiting from the technology now but weren't corrupted by it." (87:29)

5. Generational Nostalgia

• Gen Z is more nostalgic for the 80s (think: "Stranger Things") but the crew thinks the 90s are truly the “peak America” (96:23).
• Lack of distinct culture for the 2000s (“the aughts”) due to rapid change and the invasion of the internet.

6. Comments and Listener Interaction

• Shoutouts to fans, teachers using “Hello folks” and “Hey bear” as classroom routines, musicians-turned-teachers (“Mr. Holland’s Opus”), and a math teacher comparing the iterative process of lesson-planning to developing comedy sets.
• Aaron receives praise for introducing a listener to the "yard ball".

7. Food Allergies in Generation Alpha (and Zalphas)

• The rise in allergies—possibly due to over-cleanliness or food quality—and Amish children as an outlier (only 7% with allergies compared to 36% average).
  • Dusty: "That doesn't sound very Alpha at all. Yeah, we're allergic to everything." (99:17)

Notable Quotes & Memorable Moments with Timestamps

• Ryan (on generational naming):
  “Tom Brokaw wrote a book called the Greatest Generation… and it stuck. That’s where it came from.” (63:29)
• Nate (on performing in a suit):
  “These shows are getting so big. I’m trying to meet them with the professionalism that I think they meet me… it just doesn’t feel right” (15:05)
• Ryan (on club wall signatures):
  “I was just at Chattanooga and they said, sign the wall. But we only let people who sell out a show sign.” (31:04)
• Aaron (nostalgia):
  "Why do you think the 2000s doesn’t have as distinctive a thing as the 90s?" (96:39)
• Dusty (on allergies):
  “Now there’s too much glyphosate in the soils… It ain’t these kids’ fault.” (100:13)
• The Group (teasing Dusty about being on a club mural):
  “That’s four comics and one other guy… I don’t know who that other guy is.” (59:27)
• Ryan (reflecting on generational unity):
  “I specifically know, spending time with my grandparents, it felt like they were kind of all united… a similar mindset, which I don’t know if that’s existed like that ever since.” (105:01)
• Aaron (on generational titles):
  “You think the world ended in 2012 — we’re just kind of hanging around…” (97:31)

Important Segment Timestamps

• [01:01] – Ryan Hamilton’s welcome; Netflix special announcement
• [10:08] – Brian’s Jacksonville and Universal Studios stories
• [14:46] – New suits and stage attire discussion
• [19:36] – “Raking leaves jackets” and club comic fashion
• [25:38] – Brian’s Salina, Kansas gig disaster and traveling for corporates
• [30:45] – Comedy club wall signing debate
• [46:03] – Listener comments and teacher shoutouts
• [63:05] – Start of main generations discussion
• [87:16] – “The Lucky Ones” / Oregon Trail generation
• [92:57] – Gen Z’s media consumption and nostalgia
• [98:43] – Generation Alpha and allergies
• [105:01] – Reflection on the Greatest Generation’s unity

Recurring Bits & In-Jokes

• Dusty’s “allergic to everything” riff on kids today
• Light-hearted jabs at each other’s age and club success (“I never played Acme!”)
• Old club horror stories (bad condos, wet sheets, “get my stash” encounters)
• Ongoing banter about food, allergies, and American cities fallen on hard times

Final Thoughts

The hosts and Ryan agree that labels, nostalgia, and perceived differences between generations often tell us as much about the culture doing the labeling as it does the people being labeled. Technology has accelerated change to a dizzying pace, but some things—like commemorating a gig with your signature or commiserating about bad travel—never change.

The episode wraps with a look forward: Netflix specials, upcoming gigs, and the eternally debatable question of which generation is truly the “greatest.” The hosts have fun, stay reflective, and keep it light—true to Nateland tradition.

For more:

• Ryan Hamilton’s Netflix special tapes Oct 4 at The Neptune, Seattle
• All hosts’ show dates announced at the episode’s close