

#156 – Tim Dillon: Comedy, Power, Conspiracy Theories, and Freedom
19 snips Jan 29, 2021
Tim Dillon, a fearless comedian and podcaster, dives into controversial realms like comedy’s role in society and the peculiar intersection of humor and politics. They discuss the complex narratives of mortality and debt, weaving in dark humor to explore genuine human experiences. Dillon also critiques the influence of AI on relationships and expression, while navigating the challenges of self-censorship faced by comedians today. With candid anecdotes, he unpacks the nuances of fame, power, and the shifting landscape of modern comedy.
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Unpaid Tombstone
- Tim Dillon wants his tombstone to read "This has not been paid for".
- He finds humor in burdening his living relatives with the unpaid debt.
The Boating Accidents
- Dillon recounts a story about a friend's alcoholic father who jokingly stuck them with a large bar tab.
- He highlights the complex mix of fondness and disapproval such characters evoke.
Bad Advice
- Dillon critiques the advice "follow your dreams" and "you can be anything you want to be".
- He argues it's unrealistic and sets most people up for failure.