Moontower 2018 Interview: Tim Dillon Finds Comedy In Unexpected Places

Tim Dillon is tired of people trying to win arguments on stage. It’s boring. He’s much more interested in discovering comedy. While many profiles of Mr. Dillon tend to focus on the fact that he has conservative leanings, Dillon himself sounds less convinced. “You believe in free speech, you’re conservative. I don’t know. I try to be funny.” He’s definitely succeeding there.

Mr. Dillon was recently named one of Rolling Stone‘s 10 Comedians You Need to Know and has Netflix and Comedy Central specials slated to premiere later this year. He has a celebrated podcast, Tim Dillon is Going to Hell, where he defends “CEOs, dictators, con artists, thieves, tax cheats, & crime families” and leads a double decker bus tour of New York where he examines on the murky dealings of the mega rich. They’re both very funny. He talked to Moontower about acting on Sesame Street, serving on a murder trial, and how focusing on winning arguments can sink comedy.

On starting stand-up

I was a juror on a murder trial and every day on the murder trial a prosecutor would talk all about life and death. I don’t know if you’ve ever seen a murder trial but it’s a lot of mortality. You know how some people go on like a retreat, to get themselves together? I had a murder trial on Long Island. It was about a week and a half, but at the end of that I said to myself, “You know what? I’m gonna die one day. I’m gonna regret not doing certain things.” So I then went and started to do those things. One of them was quitting drinking, one of them was starting standup comedy, and one was coming out of the closet. I had been in the closet until 25, which was very late in today’s standards. By those standards, 2010, it was still late. So those were the three things I did, and all within like a two to three month radius.

On acting as a child

I was on Sesame Street a few times and I did a lot of theater in New York City and then I traveled around the country with the show, Annie Get Your Gun. I was in sixth grade, and that was kind of the end of it. I spent two months on a tour bus, and we lived out of motels, and I performed in a different theater every night. It was fun, but it was really exhausting, and kind of mentally taxing. I don’t know if that’s what I signed up for. I thought I was going to be like a movie star and I wanted to be Jonathan Taylor Thomas and then you find out you’re performing in Gainesville, Florida. So I kind of was a disillusioned, cynical, bitter, resentful, 11-year-old. So that’s interesting.

On Ideology and Comedy

If you shut down any part of your brain, to follow any ideology, in an intensely rigid manner, it makes you less funny, in my belief. So the reason that that people say I’m all over the place, is that I genuinely and try to be humorous and look at things from different perspectives. I mean that’s it. I’m sort of all over the map. I think that there are good ideas everywhere. I’m not religious, and what you find is that most people are religious, whether they follow a conventional religion or not. Most people in their thinking and their belief system are religious. And people really just want to win arguments. You don’t wanna learn more. And I was a debate guy in college, I know what it’s like to win arguments. It gets boring. It’s kind of not interesting after a while. You don’t grow, you don’t learn or evolve at all if you are just concentrated on winning. So that’s kind of why I’m all over the place.

On his New York Bus Tours

I was a tour guide on a double-decker bus in New York City. I would give these wild, subversive tours of New York. I would pass the Empire State Building and I wouldn’t say anything, but I would talk about money laundering and human trafficking. A lot of people were like “We just came to see Jersey Boys and this feels like an attack,” and it was, but, in New York I always felt like you had to explain more than just the monuments.

When I started stand up I didn’t need to do that anymore as a job, but for the New York Comedy Festival, I rented a tour bus and I sold tickets to it, because I still love the idea of that. New York City, for a very long time, has been the home of the mega-rich. The history of New York City and the role that real estate plays a role in the way money moves around the world is really interesting to me. I had done a lot of research and I read a lot about these people. I like the idea that we’re focusing not so much on the statues and monuments and the New York City Hall, but we’re looking at the illicit streams of money flowing in and out of a place. There is so much of what you would just call institutionalized corruption everywhere, that that’s what we show them. I try to make funny and interesting and kind of interesting and pull that veil back for people.

On Coming to Austin

I love Austin, it’s a great city. I love the food and I’m looking forward to eating. It’ll be a lot of fun.

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