Summary of 982. - Whitmer Thomas

Overview of How Long Gone with Whitmer Thomas

Chris Black and Jason Stewart chat with comedian, musician, and skateboarder Whitmer Thomas about his new HBO special, the long and chaotic process of making it, and the many weird side quests of his life: gambling, Hooters, vintage clothes, movie roles, and trying to stay financially afloat as a working artist. The episode is equal parts culture talk, behind-the-scenes comedy special breakdown, and very funny riffing on fame, style, and the economics of making art.

Main Topics Discussed

Whitmer’s new HBO special

• Whitmer talks about the special being finished long before release and how much work went into editing it.
• He explains that the special included a mix of stand-up, music, and personal footage, which made the post-production process unusually complicated.
• He says he had to go back to Alabama and track down old skate videos and other archival material himself.
• He also describes some frustrating rollout issues, including:
  • poster mistakes,
  • social media posting the wrong clip,
  • and general confusion around how to market a special that doesn’t fit the standard “comic holding mic and shrugging” template.

Comedy, style, and persona

• The hosts praise Whitmer’s ability to tell stories that feel personal and emotionally grounded without becoming overly sentimental.
• Whitmer says he prefers storytelling-based comedy because it feels more natural than just firing off jokes.
• He discusses how comedians today often mine their real lives for material, and how that can feel limiting even if it’s effective.
• The conversation also gets into the value of having “LOL guys” around you — people who can help you laugh through chaos rather than just be relentlessly sincere.

Music, skateboarding, and old footage

• Whitmer reflects on using skate videos and older footage as part of the special.
• He talks about the role skateboarding still plays in his identity and how it intersects with his comedy and stage persona.
• There’s a lot of crossover discussion about subcultures, music scenes, and how those worlds show up in his work.

Acting and film roles

• Whitmer mentions appearing in a movie called Weapons, playing a father, and being excited to be part of a larger project.
• He also talks about filming another horror movie in Budapest and how out-of-place he felt in the middle of an international cast.
• The hosts ask about recognition and whether people know it’s him on screen; Whitmer jokes that once his hair is combed, he becomes nearly unrecognizable.

Gambling and financial survival

• One of the funniest recurring threads is Whitmer’s gambling habit.
• He admits to spending a lot of money at casinos while touring, often using gambling as a fallback when money gets tight.
• He describes:
  • collecting casino points to stay in hotel networks,
  • losing essentially all the money he’d made,
  • and then later doing casino-themed content as a way to try to win it back.
• His general logic: if he’s already broke, gambling feels like a way to either stay broke or maybe get out of it.

Clothing, merch, and “shrimp hats”

• Whitmer tells a great story about a hotel mistakenly throwing away a bag of his clothes, including vintage shirts he valued highly.
• The hotel staff didn’t understand why old T-shirts could be valuable, forcing him to explain the concept of vintage clothing and Depop receipts.
• He also talks about his shrimp hats, which have become a surprisingly lucrative merch item.
• The hosts note that the hats have likely made him a serious amount of money, and Whitmer confirms they’ve helped keep him afloat.

Hooters and beverages

• Whitmer openly declares his love of Hooters, especially for buffalo-style food.
• He says he doesn’t really drink beer, which the hosts find slightly countercultural for a Southern guy.
• His default order is more in the “vodka cranberry / sweet drink” lane, and he jokes that he came to alcohol relatively late.

Notable Takeaways

• Whitmer’s special is highly personal and blends stand-up, music, old footage, and diaristic material in a way that makes it feel distinct from standard comedy specials.
• His career is a constant balancing act between art and survival: acting roles, merch, touring, and comedy all feed the same practical machine.
• He has a strong sense of humor about poverty and chaos, especially when describing gambling, financial stress, and absurd industry mishaps.
• The episode highlights how much of his appeal comes from specificity — his stories feel lived-in, weird, and emotionally real.

Memorable Bits and Quotes

• On comedy specials and rollout:
  • The wrong trailer clip got posted, and Whitmer was furious because it revealed the wrong part of the special.
• On his stage persona:
  • He jokes that people can’t even remember his name properly, with “Whitmer” often getting turned into “Whitmore,” “Whitmire,” or “Whitney.”
• On gambling:
  • He describes casinos as both a vice and a survival tool.
• On merch:
  • The shrimp hats are a real business, not just a joke.
• On his identity:
  • He comes across as someone who knows exactly how strange his own life is, and can make that strangeness funny without flattening it.

Release / Recommendation Notes

• Whitmer says the special is coming out on HBO, with the release date mentioned as August 14.

• If you like:

  • alternative comedy,
  • emotionally specific storytelling,
  • skate culture,
  • weird merch entrepreneurship,
  • and behind-the-scenes showbiz chaos,

  this episode is a strong listen.