EXCLUSIVE: 'It's all a cautionary tale' - Tim Dillon has seen the end

Self-styled 'tour guide to the end of the world' talks cancel culture, Epstein, family betrayal and why society feels like it’s in its final act

May, 2021

‘I look at my father and it’s like he’s been lobotomized, but maybe he’s figured something out,’ 36-year-old comedian Tim Dillon tells me. ‘I may find out it’s the only way to survive.’

Dillon is increasingly now recognized as heir-apparent to countercultural comedy greats Bill Hicks and George Carlin, but it wasn’t so long ago he was selling subprime mortgages and photocopiers, and working as a New York tour bus guide. A recovering addict (11 years clean), his life changed in 2019 when podcast king Joe Rogan spotted his defense of canceled comedian Louis CK on Facebook and invited him to be a guest on The Joe Rogan Experience, a podcast whose global audience is measured in the hundreds of millions.

‘My entire career shifted at that moment, because of his generosity,’ Dillon says. ‘He gave me that platform and he kept having me on.’ Today, Dillon’s own podcast, The Tim Dillon Show, for which he says he doesn’t prepare — ‘it’s just me talking to my friend twice a week’ — generates more than $100,000 a month through Patreon subscriptions, and his audience is growing rapidly. Candace Owens and Jordan Peterson have made guest appearances. Unsurprisingly for a man who until recently was living hand-to-mouth, he is an ardent supporter of podcasts. He considers them relevant in a way mainstream media can no longer hope to be.

‘Donald Trump won an election in no small part because he was a wild, unpredictable figure. That should have taught the mainstream media that people are much less impressed by the stilted interviews you see on The Tonight Show, where people are talking for three minutes about a vacation they went on, and all the jokes are preplanned and it’s meant to feel spontaneous, but it feels the exact opposite — and everything is sandwiched between commercials for products you don’t use.’

The idea of moving into the mainstream — to host, say, a family-friendly chat show, à la Jimmy Kimmel or James Corden — fills him with horror. ‘I couldn’t think of a worse thing to do. What could be less interesting than an entire family consuming the same entertainment? How grotesque. How grotesque to make something that appeals to a nine-year old and someone who’s 75.’

Devotees of Dillon’s podcast could be forgiven for suspecting a transition to primetime would not last very long anyway. He rages (usually by making very specific allegations) against prominent members of political and social elites. He mercilessly mocks the likes of Meghan McCain or the lesbian couple (‘desert dykes’) who last year objected to the state in which he left their Joshua Tree Airbnb rental. It seems a miracle nobody has tried very hard to have him canceled, or sued him into oblivion.

‘Libel suits are very difficult to win,’ he says, unconvincingly. ‘As far as canceling me, there’s nothing to cancel, because I just entertain my fans. I’m not forcing myself down your throat; that’s why I don’t want to be on mainstream TV. If you put me on CBS and the audience flips out, or someone says “This guy’s offensive”, then CBS has got to decide if I represent their core values. I only have to entertain my fans, thanks to the technology we use.’