CANCEL-PROOF: Tim Dillon's big, gay get-out-of-jail-free card

Some statements are politically incorrect, some are defamatory, and others are outright illegal. For Tim Dillon, it's all alleged.

For the better part of a decade, the stand-up comic has delivered what can be considered some of the most offensive tirades ever broadcasted. The problem is, a lot of people agree with him.

'I don't want to live in a right-wing Christian theocracy.'

Nothing to lose

Perhaps it was in 2020 when Dillon took a turn for the worse, suggesting during one of his trademark rants that Bill and Hillary Clinton should be respected "even if they are murderers."

Dillon's verbose way of comically beating around the bush always, eventually, gets to the point, but he's not willing to show his cards right away. First, audiences need to hear about how tough a negotiator Hillary is, or how American mothers revered Bill through his political journey and his time as governor of Arkansas.

After about eight minutes, viewers are ready to hear how far the mighty have fallen. In this case, it was Hillary's transition from committing murders and "arranging the suicides of many of your Secret Service people" into hosting a new podcast. Dillon's show is like watching the news being broadcasted by someone who is on death row and has nothing to lose.

Through this method, Dillon laughed his way through the next year, amassing a reported 23,000+ Patreon subscribers who garnered him $1.5 million in revenue. In 2021, his show was labeled the seventh-richest podcast on the air.

By 2023, Dillon's production had lost any and all guardrails, as seen by clips titled "My Son's P*ssy Rant," for example. Looking to address transgender controversies, the 41-year-old provided adequate prefacing: "I don't want to live in a right-wing Christian theocracy," Dillon began, priming the conservative portion of his audience.

After reminding his viewers that such topics are always handled with tact, Dillon expressed that he isn't a fan of children being rushed into operating rooms or told to use puberty blockers.

While asserting that he is not trying to take a side in the culture war, Dillon asked a simple question: "Are we going to be better at making a vagina out of someone's bowel? I hope we are," he said.

"Literally not kidding, no joke," he added, saying he dreamed of a future where such surgeries become as easy as going to the dentist.

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Burying the lede

This wasn't the first time Dillon tactfully addressed the excesses of the MMIWG2SLGBTQQIA+ community. In a video from 2019 titled, "The problem with 10 year old strippers," the comedian informed listeners that as a gay man himself, "if you're a woman and go 'I'm a dude,' it's still not working."

Much of Dillon's show is figuring how to say what is not supposed to be said and then saying it anyway.

"You can say it 'cause you're gay," Joe Rogan told Dillon in 2020, citing that his wife doesn't believe Dillon is actually a homosexual. But even if Dillon does have a "get-out-of-jail free pass" for gay topics, as Rogan claims, he still has to find a way to say more broadly incendiary politic remarks, too.

Dillon admitted to Rogan that he may "look too racist" to say certain things, but he says them anyway.

Case in point: episode No. 355. Dillon tells viewers about his trip to Denver, doing comedy shows and having a great time. After promoting his tour dates and talking about his observations in the Mile-High City, the New Yorker made another one of his famous comedy-to-politics transitions.

After about four minutes of a monologue culminating in the eating of a green chili burrito, Dillon stated, "In that time that I was away from you all, I imagine you've heard about, and this is not a big deal, it's the summer and the Obamas killed a sex slave."

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Michael S. Schwartz/Getty Images

Loose lips

Whether Dillon is accusing the Obama family of murder, the Trump administration of being in a mafia-like government, or Vice President JD Vance acting clueless about Jeffrey Epstein, the backdrop of the entire podcast has, and always will be, Dillon's freedom of speech.

Dillon has vehemently, and perhaps even seriously, defended his right to free speech in the face of people who actually wanted to silence him. He discussed this when he was fired from the Riyadh Comedy Festival over jokes in which he said Saudi Arabia has slaves.

In his defense, Dillon said he was actually complimenting the Islamic regime by saying, "Slaves are probably hard workers and, for the most part, agreeable."

Things turned more serious when Dillon addressed comments his publicity team had allegedly told him about how there are certain topics he doesn't need to touch because they might hurt his career, but Dillon soundly rejected the idea: "On my own show, in my own country, where I have the freedom to speak and say the things I want, I'm going to be funny and I'm going to be who I am. And if you're not buying that, you don't have the right to tell me on my own show."

So whether Dillon is calling out "Good Morning America" for promoting an 11-year -old "drag kid" or being told he's a "self-hating gay guy" or not even really gay at all, he knows exactly where his get-out-of-jail free card lies: with his audience.

"The business doesn't have any teeth any more. They can't tell me what to do or say. What? They're not even offering anything."

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