Tim Dillon doesn’t really fall into any particular comedic niche. He is simultaneously a boisterous, conservative-leaning Long Island native and a thoughtful, homosexual foodie with a soft spot for frozen yogurt. His confrontational style puts audiences on the edge of their seats, but with no loss of enjoyment or laughter. Tim Dillon is a comic you really remember.
Dillon’s podcast, Tim Dillon is Going to Hell, is devoted to “[taking] a hard, critical look at the people that society’s decided to hate: the billionaires, the dictators, the CEOs.” As Dillon puts it: “There are bad things in the world, there are bad people, and thank God for them. What’s good without evil?” The wealthy are of particular interest to Dillon, inasmuch as he believes that their success stories are often manufactured, misrepresented, or generally overlooked.
November 1-3, Dillon will be taking part in the New York Comedy Festival by giving a tour of “The Real New York,” which is to say: he will be hilariously yelling at a busload of comedy-going tourists about their own shortcomings in comparison with the accomplishments of New York’s social elite (and so much more!). After the tour for November 1st rapidly sold out, producers quickly added a November 2nd date, which quickly followed suit. The producers of the festival have now added a third night, still available at the time of writing.
I recently sat down with Dillon to talk about his approach to comedy, how he sees himself in relation to the comedy scene, and his obsession with the lifestyles of the rich and famous.
How’s Tim Dillon is Going to Hell going? You’ve mentioned toward the end of a few of your episodes that you’re hoping to have a “lying expert” on. Any luck with that?
We’re looking! I’d love to have somebody who used to work for a government agency or something on, but right now we’re trying to get a high-end realtor in New York. One of the top real estate agents, because that, to me, is fascinating. I want to know what it’s like to be at the top of that business in a city like New York, or what that takes. Those people aren’t coming on my show. We’ve had some real cool people come on, but a lot of people, especially people in those areas that are very conscious of their brand, are a little reluctant to come on, which I get. If they are going to do something like that, it’s going to be like Barbara Walters or something.
Are you brand-conscious yourself?
The thing is, my brand is loose, because to me it’s whatever is interesting and funny. I think I have a definitive voice in the way that I look at the world, cynical and whatever. I don’t know that I have a brand where it’s like… I’m not worried about selling things, because I think if I’m funny, and I do things that are interesting, people will gravitate towards it.
You take a lot of controversial stands. It seems like the way you operate is when everybody’s complaining about one thing, you take the opposite stance. I mean, I don’t think it’s quite that simple. That would just be being a contrarian. I assume that’s sort of a hard line to walk.
I think what happens in comedy – and what surprised me about comedy – is how much of a pack mentality it is. It’s not at all different from anything else. Comedians like to think that they are different from a bunch of guys that are just filing into an office somewhere in Midtown Manhattan. They’re not. It’s just humanity. People want to be comfortable, they want to be liked, they want to be important. I think that causes people to, in many cases, just try to embrace this community aspect.
To that end, you see a lot of people not taking risks, not being funny. I think funny comes from the willingness to be unpopular, or to fail… to make the joke that is not what everyone is thinking. I don’t necessarily always try to do that. I don’t know if I’m a contrarian. I don’t think politically I line up with anything. I think it’s all fake. I think the election, I think it’s all pretend. I’m one of those; I believe in power structures and all that stuff. I would much rather talk about what’s generally called “conspiracies,” because I find them to be closer to the actual truth of what’s going on.
In comedy, I look at social media and I see everybody has lined up on one side of an issue, and I always try to see if there’s a funny way to look at it from another way.
So you’re more focused on bridging a gap than taking a contrary stance.
Yeah. When everybody is like, “We hate Donald Trump,” I’m like, “Okay, we all hate Donald Trump, but Trump’s funnier than most of you.” That’s the fact. You know what I mean? That’s a reality. He’s probably also a horrible person, he’s also funnier than most of you. I’ve seen you, I’ve gone to these shows in Bushwick, I did them for years, I watched so many of these people get up, they are not funny. It’s weird to me that out in the community of people, so many of them are failing and not doing their job, but they get on social media and they’re like… It’s as if I walked around Goldman Sachs, and started giving them advice, because I had read a lot about finance.
Be funny. It’s just trying to look from a different angle. You look at some of the comedy, the people on the highest level are John Oliver and Jon Stewart, and it’s amazing. Then you see people try to emulate that and fail, and I’m like, “Oh, well let me look at it another way and see if that’s …”
Then I beat up on stuff for fun. I make fun of improv a lot. A lot of my act improvised, and it’s not as tight as… There are improv guys that are amazing. Chris Gethard is a good friend of mine, he’s an amazing talent. I think it’s funny to talk about improv and bully these improv kids, or the Bushwick crowd. A lot of my friends are in that scene when I go do those shows. I think it’s just funny to pile on, in good humor. I did all those all of those shows frequently before… I’m in year seven of comedy, and before I did any clubs, I just did those bar shows, and if I didn’t have those bar shows, what would I have done? Even though I make fun of stuff, I think it’s funny. I’m not angry.
What do you think one of the biggest problems is right now for comedy?
It’s hard to make a living. If you look at the financials of it, it’s just hard. It’s just like, I’m going to die. It’s tough, you’re getting paid the same as comics got paid 20 years ago to do spots and stuff, financially it’s tough to do. People have to work a day job for a long, long time.
Were you doing the bus tours before you started doing comedy?
No, no. That was one of the day jobs I had to make ends meet. I’ve only been making a living in comedy for like nine months. The majority of the time, I had a full-time day job. That’s one of the things, when I look at it, I go, there are very few jobs where you have to have another job for so long. Yeah, that’s the other thing. At a certain point, I think people have to decide what role comedy is going to play in their life and what they are giving up to do it. My dad was a musician for a while, then he had me and it was like, “Well, now I’ve got to make a living. I have to make a better living.”
You tried that work-a-day lifestyle before you did comedy though too, right? I think I heard you did real estate or something?
I was a mortgage guy, I tried that, I didn’t make a lot of money, I wasn’t good at it. I was okay, but I’m not a good salesperson. That’s part of my fascination with these things that I wasn’t good at. I couldn’t shut up. I would try to sell somebody something and my boss would just go, “Dude, shut up.” I do it in general meetings where the manager’s like, “Just stop talking.” I’ll be like, “Well, you don’t like that idea.” They’re like, “We do like that idea.” I’m like, “No, no, no, but listen.” I just keep going.
I think it’s a word-economy issue. It’s why I’m better at Facebook than Twitter. It’s why I’m better at comedy than sales, because I have more time to talk. I was never happy working. I was also in the closet, I hadn’t come out of the closet until I was 25. That’s pretty late by today’s standards. I was drinking and using drugs, and I stopped that five and a half years ago. I got into comedy, I came out of the closet, and I stopped using drugs and drinking in the same three-month span in the fall of 2010. It was a weird life change.
I love that. Comedy can really help people like that sometimes. Although I think it works in weird ways too, like would you say you’ve kind of exaggerated aspects of yourself because of comedy?
Probably to some extent, but I think I’ve always kind of been a loud, talkative dude, who tends to dominate situations, which I’m sure comes from insecurity. I was a child actor as a little kid, so there was always that. When I was six years old I did my first play. There was always that weird disease of, “Look at me! Listen to me!”
Yeah. We all have that, whether or not comics like to admit it; it makes no sense that you could be in comedy and not, to some extent, want that.
Yeah, one hundred percent.
Are you happy with where your career is right now?
Yeah, I’m really happy. I think that I’m just trying to get funnier and better at things that I’m not that good at. Standup is the thing that I really, really love to do, but I have to get better at writing packets and pitching ideas and writing scripts and doing things that other people can do really well.
Do you think being a guide on a tour bus has specifically shaped who you are as a standup comedian? Or is it just that you fit into that because of how you are as a standup comedian? Or is that just sort of a chicken/egg question?
The tour bus seemed interesting, because it allowed me, every day, to have a conversation with people from all over the world. Those people had all kinds of different views on America, on this city, on everything. It allowed me to be with them. Some tour guides are great tour guides, but they don’t want to be funny. I always want to be funny. Some people want to do a one-man show, I guess this tour bus thing I’m doing is kind of my one-man show, but it still seeks to be funny.
So I would spend a lot of time with those people trying to be funny. I think that helps, and that was good, because I was in a situation where I had to think on my feet, I had to improv. Some people were angry. It’s a hellish job, it’s too hot, it’s too cold, the bus isn’t on time, these people miss whatever stop, they’re supposed to get off at Empire and they miss it. They’re angry, and sometimes you have to diffuse those situations with humor.
I guess in New York, which is already an intense training ground for comedy, you’re also doing a separate thing that is also an intense training ground for being a comic.
Yeah. It’s weird. People come to this city and it’s not a relaxing city, it’s not a vacation where you just sit on a beach. There are schedules and timeframes, and they’re all angry and upset. You gotta deal with that.
For me, the way to do that was to just be like, let me be funny and irreverent and crazy… I’m fascinated by rich people, so I talk about rich people a lot. I would just try to do something different than a lot of the other tour guides were doing. I wasn’t just like, “Oh, there’s the Chrysler Building,” I would be like, “Rich people have islands of sex slaves and chase them around!” Many people would be like, “Oh, that doesn’t sound fun, you’re lying.” Then people would be like, “Oh, I thought this was for kids.” I’d be like, “Will you shut up?”
Some people would really enjoy it. There’d be some people that were like, “Oh, this is nuts. This is really funny, I thought it was going to be like looking at the Statue of Liberty, but here’s this guy talking about why interns at Goldman Sachs should be allowed to jump out of windows.” I’m like, “Well, they were worked to death. What a great honor. Isn’t it good to be worked to death?” I have so many friends that are DJs and personal trainers, who spend their lives washing their car; wouldn’t it be great if I heard one of them was worked to death? “Ryan? He was worked to death, he was working so hard he jumped out of a window!” Go to his parents and say, “Good job. We’ve never expected this.” Some people really enjoyed it, and as you can imagine, it was not for everybody.
Yeah, I would assume it wasn’t. That is clearly something you would benefit from, though. A lot of people, myself included, go a much more comfortable route to entertain, but that doesn’t really make you memorable, and you have to be memorable if you actually want to make a living doing comedy.
Yeah. I guess part of who I am, it’s hard for me to be like everyone else, because I’m not like everyone else, you know? I think that my sexuality, the package it’s in, the way I look and sound, and the views that I have. I’m not at all what mainstream gay culture is, or what people think it is. But I’m also not mainstream straight culture.
If I get on stage and start to be like, “Yeah, suck a dick!” people are going to be like, “This is crazy. This is genuinely weird.” Some of that is like me staking out these positions, but a lot of it is like… I’m genuinely weird. I’m just genuinely alternative.
Right, you’re just sort of this weird middle of several different things that collide in weird ways.
Yeah, and my interests too. One of my episodes of my podcast was dedicated to Illuminati satanic pedophile cults. I find those fascinating. It’s very hard when you’re coming at the world from that angle, to sit at a table with a bunch of people that are like, “What about Hillary’s emails?” and I’m like, “Sit down. Sit down.” If 10 people are talking about something, to me, not only is it not interesting, but it probably doesn’t matter. You know what I mean? I really do believe, without sounding too crazy, that we are very easily manipulated on an emotional level in this country and world. One thing I talk about on my podcast is my study of the the rich, and I have done an extensive study. I funded my own study, it’s all self-educated, but these people are able to really control their emotions. On a fascinating level, they are able to make decisions from a more pragmatic point of view. I feel like sometimes everyone and people like me are just marionettes just jumping around, like “Emails!” and “He said this! She said that!” Then it’s like, “But you don’t look at the bigger picture.” It’s like: well, wait a minute, what aren’t we all talking about? What’s behind all that that we aren’t discussing? The United States military is involved in so many of these countries, we’re only talking about one or two of them. There are all kinds of things going on that are buried in the newspaper that you really have to look for. I always found that stuff interesting.
Do you just get kind of bored by the regular array of things?
I get bored, and I also think it’s, for humor, it’s territory that’s been… I’m not a reporter, I’m not a journalist, I’m still just seeking to be funny. To me I’m like, “Well, everyone’s been funny about the first five pages of the newspaper. Everyone’s looked at that stuff already.” It’s not like my act is hyper political or anything like that.
Especially with the podcast, I’m like, “Well, what’s an angle that we’re not looking at that also could be funny?” An angle that’s not simply, “Trumps a piece of shit and Hillary is a cold liar.” We have their archetypes down. What else is going on? We’re so invested in personalities in this country, and we just don’t understand systems. We don’t understand systems all.
Absolutely. We’re growing more into focusing on celebrity and ego, rather than the systems that each individual is a part of.
The criminal justice system is so horribly racially biased. It’s a systemic problem, it’s the way the levers work. It’s wrong. To fully understand it, and I don’t even fully understand it, you have to research and read, and then you realize it’s a systemic problem. Then what is hard is people realize, “Oh, if it’s a systemic problem, I play a role in it. I play a part.” I used to drive around Long Island just getting high for years. I was stopped by the cops a bunch, went to jail, but never got shot.
Privilege is annoying word, and a lot of people use it in these annoying ways, but it’s an absolutely undeniably true thing. If I look back at my childhood, and I go, “I could have went to jail, I could have been a felon, I could have never had a job.” People don’t want to live in that world. People don’t want to live in a world where they didn’t earn everything.
Right, where you’re part of a system.
Right, you’re part of a system. It’s easy to be like, “Trump sucks! I don’t like Hillary, she’s corrupt!” Oh stop it. Everyone’s corrupt on some level. I used to go into 16 Handles and I would try each of the yogurts, and never buy a yogurt and leave. Then they would stop me and they’d be like, “Stop doing that.” I’d go, “You shut up!” I said, “Don’t be a company man. You work at 16 Handles, don’t let them make you lose your dignity right now. Don’t let them. Look at me, I’m a person. You’re in this larger organization telling me this yogurt matters; it doesn’t matter. They’re not paying you fairly.” That person, sometimes they would look at me and they would just go, “You’re right.”
I’m sure that would at least be the most interesting part of their day.
One lady told me, “I don’t care about the company, it’s just your weight.” I said, “That’s fair.” I grew up in the 90s where it was like nobody gave a shit. Everyone cares about their jobs now, it’s disgusting.
Is there anything that specifically gives you hope about comedy right now?
There’s a lot of opportunities now to do crazy stuff. Jo Firestone or Chris Gethard, the people that are really pushing the boundaries of what we consider comedy, I think they’re great. Look at Bill Burr and Louie and all these great comics, there are so many great people. The idea that we could see these guys, and really appreciate them, it’s amazing. I feel lucky to be in New York. Absolutely. I think there’s a lot of hope. I think there’s a lot of funny people.
What would you say in your mind is the biggest mistake a comic could make?
Trying to make money too quickly. Wait to get good! Don’t try to force something. I wouldn’t immediately be like, “I deserve it.” I’ve only started to deserve money recently. Most comics don’t deserve money. I barely deserve it now. It’s been seven years. Some nights I deserve it more than others.
What do you think qualifies as deserving payment?
I think you gotta be true to yourself; you gotta do stuff you’re proud of, and you gotta get them on your terms. I love crowd work, I love riffing, I love the intersection of when I have a bit and I can ask you something and build off your response and turn it into something. I love talking through stuff. My comedy is not like the tightest thing in the world. There are punchlines, there are jokes, but it’s like, I like the space to be loose. Especially in a long set. You’re headlining somewhere or something like that, the idea that I can be like, “There’s this bit I have, let me try to build on it.” So yeah, I think part of it is, you’re doing well and you’re measuring yourself against the other comics on the show.
It is okay, in your mind, to measure yourself against other comics? I feel like a lot of comics disagree on that point.
Yeah, I think it’s fine. I’ve been in situations where I thought I did really well, but then I watched a Mark Normand go up, or someone else, and I’m like, “Oh yeah, I didn’t do that good, I just did fine.” You need that. Because a lot of it is like, you shouldn’t measure yourself against comics in terms of your value or your worth, but at any given moment, if you’re evaluating a certain set, or a certain reaction that they got out of an audience that you didn’t, I think that’s fair.
Your bus tour has sold out twice already.
And they’re adding a third.
Wow. Do you think this is going to become a regular thing?
We’ll have to see if people like it.
Are you going to be doing your regular routine?
No, no. It has nothing to do with standup. “This is why you’re a pig” is the subtitle. People say, “I’m not a pig. I went to a state school and I married someone I love, and we do 5Ks and I’ve got two kids.” Oink, oink, you’re a pig. Why are rich people rich? They’re not like you. F. Scott Fitzgerald has a great line in The Rich Boy, I think, where he says, “Let me tell you something that the rich do differently from you and from me: they are cynical where we are trusting, and they are soft where we are hard.” I’ve always loved that. These are real human beings. I’ve always been fascinated by these people, I think because they won’t have me. This is a different set of folks. It’s always fascinated me. How do you get there? That’s a whole different world. Fifth Avenue, Park Avenue, it’s fascinating. You start thinking about the schools they go to, the social clubs they’re a part of, and you realize it’s a small world. Their world is designed to stay small.
That was always fascinating to me, it’s like these people that stay rich. There are these crazy people who believe the world is run by lizards, I don’t believe that. A lot of their ideas, they get it from the fact that these bloodlines, and these families stay very tight, very exclusive.
Several barriers exist to someone like me from a community like that. Even if I made lots and lots of money in entertainment, there are certain codes, beliefs, ethics that are common to that community, and they’re shifting, they’re always changing. I had a guy, Russ Baker, on my podcast, he goes, “That community, they’ll sue each other and they’ll fight, but the minute an existential or external threat comes along, they will unite to vanquish it.’” That’s fascinating to me. It’s a system preserving itself.
Earlier you were talking about how the fact that the rich are so cold and aloof is part and parcel of why they’re successful; do you try to emulate that? If you found, like, true love, do you think that would hinder your career?
I think if I found love it would harm the person I found it with. I don’t know if it would harm my comedy. I think I can retain my work ethic. I don’t know. It’s an interesting question. If you found that all-encompassing love… When you really fall in love with someone, you start making stupid decisions. That’s why rich people guard themselves against it. If you fall in love with someone, and you’re in love with them, and you make a bad decision, in order to keep that bad decision going, you have to make a smaller bad decision, and then you’re married and legally in an arrangement with someone who may not share any of the values of that world that you’re in, but you’re with them because you fell in love with them, and that feeling kind of fades. That feeling of love will fade, I think. That in itself is interesting. It really speaks to the idea that you need a partner more than a husband or wife.
It’s the idea that they’re like us. That they are just like us, and they’re on the couch and one of them farts and the other is like “Did you fart!?” That’s not it at all. There is this weird, comforting thing that like, because if everyone is like you, then you’re just a couple good decisions away from it. The thing is, a sociopath doesn’t sell. You can’t go to Hollywood, and when somebody asks you, “Why are you here.” You go, “Well, I stepped on everyone’s neck. I had friends that looked like they were doing well, I distanced myself from all of them, I didn’t have a relationship for 10 years, in fact, I didn’t even feel anything, I was a hollowed out person. Even now, Barbara, I still don’t really feel much. I look at you, and you could explode in front of me…It would do nothing to me. I don’t feel the way that you do. I was able to compartmentalize my feelings, and I’ve become a hollow robot.”
“I’m really worried about climate change and the poor.” People go, “Oh.” They don’t give a shit! They don’t care! They are living in a 20,000 square-foot home in Malibu; they don’t care. The real story, which is always more interesting to me, that’s the real story of how you got there. Your ability to just never take “no,” to just keep going. That doesn’t come from a healthy place, I really don’t believe it does. For some people it might, but for the majority of people, you made these little sacrifices, you do these things, you compartmentalize these emotions, you get tough, and I think that’s the interesting story. That’s the story I want to hear. I don’t want to hear, “Well, mother always said I was going to be great.” It’s like, “No, but tell us what really got you here.”
I would love a real interview with some of these Wall Street people where some of these women go, “You’re so stylish, why are you so stylish?” and they’re like “I wanted, as a little girl, to really do something different. I wanted to help people. I was bullied as a little girl. Then I went through puberty, and I got pretty, and I realized that I was at a cross in the road, and I realized I could go and still be that girl that helped people, but I wanted to make everyone pay and suffer for what they did to me.” You know what I mean? That’s the interview I’d like to see. Because then you go, “I want to see the real monsters.” I don’t want to see some nonsense about like, “Well, I just love fashion.” All these people, what does this come from? What does it mean? Because I’ll be honest about my shit. I spent time in crack houses and I got into drugs; I started doing blow at 13 and was a closet homosexual; my mom is schizophrenic. That’s why I’m like this. Now I want to know why everyone else is like that.
Sure. It’s not even that it’s just disingenuous, but it literally inhibits people from understanding the world that we live in.
One hundred percent. People have these false narratives just crammed down their throat. We are at the mercy in this country of just narcissists all the time telling us, whether they are Doctor Phil, whoever these people are, they are intruding on your space, and they are at the top of cabs, they are everywhere, and they are telling you these false narratives. It’s not the way that it works in my experience.
Photo by Mindy Tucker.