For anyone unfamiliar with Tim Heidecker’s vast body of work, it’s occasionally difficult to separate his comedy from reality. Some of his projects, like the recent On Cinema Oscar Special, in which he hosts a discussion about the Academy Awards and unexpected debauchery ensues, create a lifelike world where one wonders if it’s a skit or if these idiots are actually having a serious discussion about the Oscars. Was Heidecker actually upset that On Cinema movie expert, Gregg Turkington, replaced him with a virtually unknown man named Rafael Torres or was it just a Twitter-based performance that eventually came to a head on the actual show? The fun is that it’s everything at once. The annual special is not unlike the actual Academy Awards — it even airs at the same time — but it relishes the absurdity of the entire night, and in the process becomes far more self-aware than we can ever hope for the Academy.

Apart from On Cinema, Heidecker’s surreal performance art, filmmaking, and cringe comedy have spun off a variety of politically themed projects. He’s probably best known as one half of Tim & Eric, his duo with Eric Wareheim; the two created Tim and Eric Awesome Show, Great Job! . While Tim & Eric are still active, Heidecker has also started many solo and collaborative projects, such as the series Decker (a spoof on action-film tropes, the main character of which is based on Trump), the Kafkaesque “Trial of Tim Heidecker”, an almost-five-hour-long video in which Heidecker is tried for murders he supposedly committed in the On Cinema universe, and his serious-minded Office Hours podcast. He also writes and plays satirical songs that advocate punching white supremacist Richard Spencer, poke fun at “ICE Agent Ray” in a country ballad about an ICE agent’s typical Monday filled with coffee, arresting an unarmed family of four at gunpoint, and ending a tough day with cartoons, and proclaim a sarcastic nostalgia for the innocence of classic conspiracy theories.

Heidecker’s left-leaning political views and relentless criticism of far-right figureheads have drawn criticism. Despite political differences, his absurdist comedy indirectly corresponds with the negative worldview held by many on the far right; the difference is that Heidecker’s work has a positive self-awareness and willingness to exchange ideas. The Outline spoke with Heidecker about his comedic influences, his recent projects (including a collection of “Trump songs” titled Another Year in Hell ), and why he thinks engaging in debate is important for America’s divisive political climate.

You recently released Another Year in Hell EP, a collection of songs you recorded and posted on your Bandcamp page. What made you choose to include those particular songs?

My approach to those political songs is I tend to write them quickly, record them quickly, and release them as fast as I can so they capture the moment so you can’t be confused about what I was talking because it was on the news the night before. I put them out on my Bandcamp so that people can hear them. But to put them up on Spotify and other places takes more time so the [Jagjaguwar] label and I just agreed to take what I liked from the year — there were probably a couple others that I would have liked to put on there — and put them together so there was at least a collection somewhere. I like things to be somewhat organized.

The top of your Bandcamp page says “all sales go to charity.” Do all proceeds from your Bandcamp sales go to charity?

No, it's a scam [laughs]. Yeah, I think it’s a way to raise money for various groups. I mean, nobody buys anything on the internet so I don’t think a lot of money comes in, but I think we raised $1,000 for a Jewish refugee group with the song “Ballad of The Incel Man.” It doesn’t really cost me anything to make these songs. I do everything in my home studio. If I’m not going to spend money to record an album or to make a short, I expect to not give that stuff away for free but for this kind of stuff, I just love doing it.It’s like a hobby for me, so I wouldn’t feel great about keeping that money. It’s a nice way to raise a little money for a good cause.

How do you pick what you’re going to write about?

It depends. It’s gotta be something that speaks to me. I’ll go down to my garage and just kind of fool around on the guitar or the piano. I put out something the other day about someone [Trump] lying about his height and while that wasn’t the biggest story that day or the most important bit of bad news coming out of that world, it was an angle I had that I thought was kind of clever. I’m not going to get into every policy issue. It has to kind of come to me. I don’t sit down there and really work on it everyday and analyze the newspaper. It’s normally just something that strikes me, is bothering me, or something I think is particularly absurd. I’ll go down and try to see my way through it.

Do you think you have gotten a lot more of that absurdity or things that are bothering you in the last couple years?

Yeah. It must have been seven years ago now that Herman Cain was running for president and that’s the first time that I felt as an adult that I was watching craziness in that political world. I was just thinking that this guy is a complete joke. He had put out this campaign video where his campaign manager was smoking, it looked like it had been shot on an iPhone; it was just so absurd and something we could have made. So I channeled that into an album of songs from the perspective of a lunatic Herman Cain supporter. By the time Donald Trump came around things had gotten so nuts and kind of sad and frustrating that I couldn’t think to write about anything else.

“I think that you can be skeptical and laugh at constructs of society but you don’t have to completely flush it down the toilet.”

Do you get a lot of criticism for your political views?

Totally. There’s the classic trope of “stick to comedy, your music sucks.” There’s a couple different things going on. There’s people who want the people they like to be the one version of what they like and they don’t like when that changes and that doesn’t necessarily have to do with their ideology or political beliefs. Of course, there’s a lot of people who are fans of mine who are Trump supporters or consider themselves right-wing. And then there’s people who don’t like the type of music I make. I like a certain kind of music that can’t be considered popular. It’s a folky, singer-songwriter, country, whatever that sounds like an era that I like. It’s not whatever is popular right now. I understand the criticism on what kind of music it is, that it doesn’t comport with people’s perceptions of me, and that people disagree with my particular political point of view.

You mentioned how some of your fans are Trump supporters or right-wing. On the second day of the Unite the Right Rally in Charlottesville you tweeted, “Are you a white male dabbling in this alt-right shit and today's got you freaked? Want out? My DMs are open, and I'm happy to talk.” There’s also a YouTube video of an episode of Office Hours where you spoke with a fan who definitely has some views that could be considered alt-right. Most people don’t even want to engage with the alt-right. What made you decide to keep an open dialogue?

I understand that a lot of these kids are young and are going through a transition in their life where they are very susceptible to certain clubs or ideas or ideologies. I think if we isolate them and don’t communicate with them, they are going to further entrench themselves in an ideology. I think there is a capacity for them to grow out of that ideology. I’m not saying that they can’t live in that ideology or anything, but what I’ve noticed is that it’s very cynical, nihilistic, and negative. You don’t have to live your life that way.

I think there’s also a perception from those people that someone like me who has some success and exists in the entertainment field, that we are elitist and dismissive and don’t understand what it’s like to be poor or not have certain advantages. I just like to try to remind people that I’m not some kind of out of touch celebrity who doesn’t give a shit. I’m certainly entitled in the sense that I’m a white heterosexual man, which gives me an automatic upper hand in the world, but I also worked very hard and I didn’t come from a showbiz family. I took lots of risks with my partners and we started a business and we hired people and we are sort of emblematic of the ideal “work hard,” “no handouts” kind of thing.

I hope to be an inspiration to people to show that you don’t have to be that cynical about the world. Part of that is divorcing yourself from what I consider dangerous, third-rail ideas, which are racial, anti-semitic, homophobic, points of view. If you start going down that road, it’s very dangerous. I think it’s good if I can put out into the world any kind of, “Hey pal, if you’re 22 and you’re joining a 4chan group and you’re posting pictures of people being put in Auschwitz, come talk to me a little bit or maybe you need to talk to some other points of view or be around other kinds of people.”

Do you see yourself as being able to relate to them in some way?

Absolutely. I think a lot of the success of our show and the audience we built was because we presented an anti-authoritarian, dystopian, nihilistic view of the world through our comedy. There were a lot of people — a lot of young males — that identify with that. They see the world as absurd, power centers as absurd, and not a lot to really firmly believe in, which I totally get. And we were tapping into that feeling a little bit, but at the same time the people that we work with, have worked with, and will work with are ideologically open artistic people who try to treat people equally and have classic liberal perspectives on human rights and that kind of stuff.

I understand that a lot of people were disillusioned when I came out politically the way I do because they may have wondered how I could buy into certain fundamental, what they consider to be, lies about the political establishment. I think that you can be skeptical and laugh at constructs of society but you don’t have to completely flush it down the toilet.

In your Office Hours podcast, there are comedic elements but you also discuss some heavy topics like Venezuela, Iran, and war. You recently had Abby Martin on, to discuss Venezuela.

The premise of Office Hours is a combination of my general interests as well as the audience’s interests and having a conversation about anything I want to talk about. Obviously I’m a guy that’s interested in politics and world events and as the show is a live, current events experience, certainly topics of the day come up. I don't know if I agree with Abby on everything she believes in, but I do think she says a lot of things that I do agree with and she is very intelligent and well-spoken and is a fan of the show. I’m a fan of people who are a fan of my show [laughs]. It’s a sign of good faith.

So people might say, "How could you have her on? She said this ten years ago!" or something like that. I generally am not going to restrict who I have on if I don’t necessarily agree with them. We have a small audience so I’m not too worried. I’m a huge fan of Howard Stern, of course, and his show is always so great about hearing from all kinds of wackos and nuts, not to call Abby a wacko [laughs], but all kinds of voices and different opinions. If you can successfully defend your opinion, then that’s great. Then I’m excited to hear what you have to say. I’m probably not going to have on somebody that thinks that Jews are the devil and that homosexuality is a sin, but I might because I would be interested in challenging them on those ideas. I love it. I love having people call in and argue with me. It’s exciting and I think it makes a very interesting thing to listen to.

Have politics always been something that you want to explore through your art?

Not really. Eric and I made a clear conscious choice early on that our work wasn’t going to be political, it wasn’t going to be a current events-y kind of experience. If we were going to touch on anything it was going to be from the most absurd lens possible. Certainly we touch on almost every aspect of life at some point. We will occasionally dip in there. I didn’t feel like I needed to say much in my work about it up until fairly recently. You want to grow and you want to keep yourself interested and excited about your own work and you look around the world and find inspiration in all kinds of things.

I think it’s true that for so many kinds of people there are so many people who are like, “I don’t know how you could talk about anything else right now.” Clearly, we’re living through crazy and momentous times and if I didn’t feel naturally interested in talking about it, I probably wouldn’t. I also wouldn’t feel comfortable tempering it because I would be worried it would be costing me fans.

I wanted to talk a bit about On Cinema, specifically the recent Oscar Special. It’s sometimes difficult to separate your character on the show from reality.

I don’t think we are fooling anybody that that's a real world. There are a few people who tweet me, “Is this a bit?” I’m like, “Are you crazy? What do you think is going on? Of course it’s a bit.” It’s just a fun bit that we take seriously and love doing.

What made you all decide to do the Oscar Special?

The idea originally was just to have something that people could check out during the commercials of the Oscars. One of the funny things that I don’t think people talk about too much is that these specials air concurrently with the Oscars. The big joke to me is that these guys love movies so much and they pick the one night of the year where the focus is movies and they encourage people to not watch and to watch this show that is not the Academy Awards. We love this opportunity to do a live broadcast that can feel like you don’t know what’s going to happen. We spend a long time writing and plotting out what we want to happen and setting up the conditions for certain things to happen. It’s a crazy adrenaline rush. It’s kind of scary, like imagine the way Saturday Night Live feels. It’s like a highwire act. Every year we have bigger aspirations and we use it to further the overall plot and story arc of the On Cinema world.

Do you find it difficult to break out of character sometimes?

No. It’s sort of the id version of me, I guess. It’s not like I have to do some sort of accent. I mean I’ve changed my hair and my facial hair and wardrobe, but I don’t have to separate myself too much. If you are the kind of person that might have a thought that is inappropriate or you think a certain way about somebody, you reserve that. In the case of my character, you don’t because it’s a fictional world and it’s meant to be a comedic experience. I can say terrible things, I can do terrible things to people. There’s some fun and freedom in being able to do that.