He also teaches longform improvisational comedy at the Upright Citizen’s Brigade.
Some of your pranks involve thousands of people. What appeals to you about mass pranks? Aside from sheer numbers, what function do they serve that small scale pranks don’t? The main reason that what we do now involves thousands of people is because the website got popular. We had to get bigger along with it. When I started it in 2001, it was me and one or two friends. That grew into me and a dozen friends. Then that grew exponentially over the years. It was never the idea to do massive participatory events. It’s really exciting to know that I can send one email to a mailing list and have two or three thousand people show up to partake in the event. Part of that thinking involves figuring out if the idea is funniest if thirty people are involved or 3000 people. But I do try to come up with projects that can scale as large as possible. It’s exciting to me have the chance to involve a 15-year-old kid from the Bronx who might not have that kind of opportunity otherwise. And I don’t mean that a 15-year-old kid from the Bronx in particular wouldn’t have the opportunity; No one has the opportunity to do something collaborative in a public space with thousands of other people. To be able to provide that is really fun.
How many of the pranks that you pull are based on your own ideas? Maybe 60% of the projects have been stuff that I’ve come up with pretty much on my own. There’s always a brainstorming process, but it’s not formal. It’s not like the people I work with are comedians working in a writer’s room. We don’t have meetings. We don’t even get together and drink. Not formally anyway. I get a lot of ideas emailed to me by total strangers. 99 out of 100 of those end up not being all that interesting.
Where do your ideas come from? I get a lot of ideas just from being somewhere in the city and seeing something unusual and then visualizing a way to make it funnier or more interesting. For example, I was commuting — this is maybe a year ago — and I had to transfer where the E train meets the V train at 53rd and Lexington. Everyone around me looked miserable. It was so crowded; we were all packed in like cattle. That experience inspired me to do something with the escalators in that particular station. That idea ended up as a prank called “High Five Escalator” where we positioned signs along the escalator and then had them end with a guy high fiving everybody. Or another time I was walking in Manhattan and saw a ledge along the side of a building that I thought was peculiar. It was maybe four feet off the ground. So I got the idea to put to a suicide jumper on that little ledge. I come up with a lot of things just by getting out of my apartment.
What was the best prank someone ever pulled on you? In college I had a pretty elaborate prank played on me. I had an apartment that was pretty close to all the bars in Chapel Hill. This particular year UNC was playing in the NCAA Final Four. On, I can’t remember, I think it was a Thursday or Friday morning, my friend printed up about a thousand posters announcing a party at my apartment. “Free alcohol and live music — Don’t miss the party of the year after the UNC game.” That kind of stuff. The fliers even included my address and a map to how to get there. That same morning, I saw the flyer on my car’s windshield, stuck under the wiper. Of course, I thought my friend was trying to make me think that he put the flyers up all around town. Then I got to school and saw the flyers on every bulletin board and thought, “Oh, he actually did put them up all over town.” The thing I was actually mad about was that I was planning to have about twenty friends over that night to watch the game and I ended up locking my door, turning the lights off, and hoping people didn’t show up.
You also teach improv comedy. Does performing a prank feel at all different from improvising comedy? There’s some skill overlap but ultimately I regret including the word “Improv” in the name because we get people commenting on YouTube that “This is clearly not improv; This was planned; You’re idiots.” That’s pretty annoying. But even if we have carefully planned out what we do — and sometimes we even have a script — you can never plan for how people will react. People are always variable. You have to be able to react to them in the moment. Aside from that, the skills of not breaking character, keeping a straight face, being able to improvise dialog — those are applicable to pranks and improv.
What was the last creative thing you did? Last night I was in Baltimore and there was a police officer at the bar where my friends and I were hanging out. I had to creatively figure out how to discretely take a photo of him. I wanted it because he reminded me of my favorite tv show, The Wire. I ended up getting a nice photo. It made for a great Tweet.