PLAYBOY: On Comedy Central’s Kroll Show you’ve created a vast universe of characters, including Fabrice Fabrice, Bobby Bottleservice and Aspen Bruckheimer. Do they just pop magically into your brain, or is it an arduous process involving math equations and dry-erase boards?

KROLL: It’s a combination of things. Usually a voice will pop into my head. Sometimes I’ll start playing around with it in the writers’ room, doing the voice and seeing if it lands. When I lived in New York I got a lot of inspiration on the subway. It was great for research. It’s tough in L.A. because it’s a solitary existence. You end up having to do a lot of research on YouTube.

PLAYBOY: Which of your characters are you most likely to slip into during sex?

KROLL: I developed Bobby Bottleservice by talking to girls—my friends mostly—and pretending to hit on them. Their responses were a combination of “Ugh” and “Oh, that’s funny, because that’s the kind of douche-bag who hits on me all the time.” But there was also a weird part of them that liked it—that liked a guy who’s passionate and loves women, even though he’s, you know, kind of a juice monster. [laughs] Bobby, in the right context, isn’t a bad one to channel. He’s young and wild and full of life and passion. You could do worse.

PLAYBOY: Making people laugh is part of your job. Do you lose your sense of humor when you’re not at work?

KROLL: Sometimes I have trouble watching comedy on TV or whatever, because I’m so accustomed to looking at the mathematics of how comedy works. I think if you talk to a lot of comedians, if you ask them what shows they watch, most of them will tell you they can watch only dramas. It’s just not relaxing to watch a comedy. It’s relaxing to watch a football game or House of Cards. You need that release.

PLAYBOY: What’s your release? Is there a certain genre of entertainment that lets you unwind?

KROLL: Honestly, my release is flipping through channels. At the moment I’m binge-watching The Wire. [laughs] That’s right, I’m on the cultural forefront—from 10 years ago. I also like watching football. I like playoff sports, generally. I like it when there are real stakes. I’m not interested in watching a midseason baseball game, but I’ll watch just about any playoff game in just about any sport.

PLAYBOY: You’re on an FX show called The League, about a bunch of friends in a fantasy football league. Prior to joining the show, had you ever been involved in a fantasy sport?

KROLL: Not at all. But the entire cast of The League is in a fantasy league together, which is kind of awesome. I’m not having the best season thus far, but historically I’m one of the top guys in our league. I’m a tinkerer, a drunk tinkerer. I’ll come home late at night and fuss with the lineup. On the show we call it “tinker stinker time,” which is the morning bathroom time on Sunday before a game—you know, your morning dump—your last opportunity to tinker with your lineup and really make it happen. I’m a master of the tinker stinker.

PLAYBOY: A few years ago Ken Marino, who was guest starring on The League, allegedly got arrested after punching you on the set. “I had my reasons,” he tweeted. Let’s assume for a moment it actually happened and wasn’t a big joke. What’s your side of the story?

KROLL: Ken Marino is a bully. [laughs] No, actually, I’m fascinated that people took any of that seriously. What happened was, Ken came into the trailer and was like, “Hey, I just tweeted that I punched you.” And I responded by tweeting a Martin Luther King Jr. quote, something like “I have decided to stick with love.” And people thought the whole thing was real. I couldn’t believe it. It was so bizarre to me. Then people were mad when they found out it was just a joke, because I guess they felt lied to or something. It was the weirdest thing I’ve ever been involved in.

PLAYBOY: We should also discuss the Bono incident. After the U2 frontman kissed your girlfriend, Amy Poehler, at the 2014 Golden Globe Awards, you tweeted later, “Hey, Bono, watch your back.” Is there still bad blood between you guys?

KROLL: I am conflict averse, but I have my limits. My thing with Bono isn’t just about what happened at the Globes. We have a long-standing conflict. It goes way, way into the past. It’s just.… [sighs deeply] This is still really painful to talk about.… I was supposed to be the Edge, but Bono fired me because I don’t know how to play guitar. Just like that—boom!—I’m out of U2. I have not forgiven Bono since.

PLAYBOY: Does it upset you when you and Amy go to Mexico and the tabloids publish your vacation photos, but all they talk about is her bikini and don’t once mention your beach body?

KROLL: It’s a total bummer. It’s a bummer that anyone would want to see a picture of me on vacation. Like, where are we as a society that it’s considered news that I went on vacation? Doesn’t the world have bigger issues to deal with than looking at photos of me in short-shorts and a weird camo hat?

PLAYBOY: You once bragged that your career has been “about as easy a ride as you could have.” What’s your secret?

KROLL: I think it helps that I grew up financially comfortable. A lot of artists throughout history came from the leisure class. They had the time to ponder things, to think about things. They didn’t have to spend every waking moment worrying about where rent was coming from or finding a shitty job they didn’t want because they needed the money to survive. Many, many artists grew up with nothing and had something deep inside that they wanted to express. But it makes a big difference if you don’t have those financial burdens and can decide, without worrying about bills, if you want to tell dick jokes professionally.

PLAYBOY: Were you a funny kid?

KROLL: I thought I was, but I don’t think my family would agree. When I was a kid, if you’d asked them, “Do you think Nick could be a professional comedian or actor?” I’m pretty sure they would have said, “He’s a sweet kid, but let’s be honest.…” When I decided I was going into comedy, I would describe their reaction as skeptically supportive.

PLAYBOY: Were you telling original jokes or just imitating what you saw on TV?

KROLL: Me and my friend Andrew Goldberg—who now writes for Family Guy—were best buddies in elementary school, and we’d re-create “Wayne’s World” sketches. I think a lot of comedians start out that way, just reenacting their favorite Saturday Night Live bits or their favorite scenes from Trading Places or whatever. But to me as a kid, it never felt like it was leading somewhere. I never thought, I’m going to be a comedian when I grow up. I never thought too far into the future. I guess that goes back to growing up comfortably—I had that leisure to relax and not think about what I was going to do with my life or how I was going to do it.

PLAYBOY: Your first time on a big stage was as a freshman in college, during a stand-up competition. You lost. What happened?

KROLL: I had never done comedy before, but I had this idea that I would get on stage and say, “God, I thought I was going to be so nervous, but I’m actually totally relaxed,” and then pee my pants. I’d have a water balloon in my pants and pop it with a pin during my set, and it would look like I’d peed myself. But I forgot to bring the water balloon, so I grabbed a sandwich bag or something and filled it with water. But it didn’t work out like I’d hoped. When I tried to jab it, it didn’t burst, and I kept trying, which ended up looking like I was furiously masturbating on stage. And then I spent the next five or 10 minutes explaining what I’d tried to do unsuccessfully. It did not go well.

PLAYBOY: Your father was a private investigator. Was that as cool as it sounds?

KROLL: From a very early age I would say, “My dad is a private investigator, but he doesn’t carry a gun and he doesn’t wear a trench coat.” He was working on a corporate level. I guess some of it was a little dangerous. The Kuwaiti government hired him to find Saddam Hussein’s money, and the Filipino government hired him to find Ferdinand and Imelda Marcos’s money. During the Hussein thing we had a cop outside our house for a while, and I guess that was cool. It felt more cool than scary.

PLAYBOY: You never wanted to follow in your dad’s footsteps?

KROLL: Not really. Obviously I went into a different field, but I learned a lot from him, especially the way he treats people. Anyone from heads of state to kids I played with in Little League baseball, he was kind to all of them. He treated everybody the same. You can go a long way in this world by just being a decent person.

PLAYBOY: You went to school on a farm in Vermont. That sounds almost ridiculously idyllic. Were you milking cows more than reading books?

KROLL: Well, if you want to get specific, there were no dairy cows. They were beef cows, so I didn’t have a lot of contact with them. You don’t befriend animals that are heading to slaughter. Otherwise it was an amazing experience. It’s this place called the Mountain School in Vermont, and that’s really where I got my first bug for performing. It was a bunch of smart, individualistic kids who were okay being weird. In high school it can be scary to be weird. But going up there and meeting all these eccentric kids, I was like, Oh, it’s okay to dress up in an orange jumpsuit and lip-synch James Brown songs while wearing kitchen clogs. It was a watershed for me. I was given permission to be a weirdo.

PLAYBOY: One of your first big TV roles was on the 2007 ABC sitcom Cavemen, based on a Geico commercial. At the time, you were probably just happy to be working. In hindsight, do you wish you could expunge it from your permanent record?

KROLL: I still think back on it fondly. I’d never had a TV show before. Just being able to act for a living was such an amazing opportunity, even though I was hidden under about a foot of silicone makeup. It took four hours every morning to get the makeup on and an hour to get it off. If I got that job today, I’d be like, “Holy shit. Are you kidding me with this?” But because I didn’t have anything to reference it against, I was like, Oh, great. I guess this is what being on a TV show is like. You’re covered in silicone with hair glued to your body.

PLAYBOY: Have you ever met a comedy idol who turned out to be a jackass?

KROLL: That almost never happens. Usually it’s just about me being starstruck. I had a small thing with Chevy Chase when I was on Community. He wasn’t a huge fan of anyone besides him getting a laugh. But even then I was like, Oh shit, I’m threatening to Fletch? That’s not too bad. Sometimes it doesn’t matter if the people you love and respect aren’t as cool as you want them to be. Whether Chevy Chase and I are best friends is irrelevant, and it pales in comparison to how he inspired me in Fletch or those Vacation movies or on SNL. I don’t need him to like me.

PLAYBOY: What’s your 10-year plan? Are you fine with being a comic until the bitter end, or do you want to make the leap to drama?

KROLL: I’d love to be able to do more dramatic stuff. There’s so much good drama happening on TV right now, like True Detective, which I think is just amazing. I’ve got such a dark, dark side that I haven’t been able to show yet. But I don’t know; maybe it wouldn’t be worth it. Doing a show like True Detective might be too much of a bummer. Dealing with dead people every day? That’s a tough one.

PLAYBOY: Do comedians have groupies?

KROLL: Sure. I’m pretty sure that’s the whole reason anybody becomes an artist. Whether it’s music or comedy or filmmaking, it’s all done in the hope that random strangers will want to sleep with you. When I got to the point in my career that women might actually have wanted to sleep with me because of whatever fame they thought I had, I wasn’t interested anymore. I was like, Do I actually want to be with somebody who’s just into me because I’m on television? But the biggest reason to say no to a groupie is that you’ve done two shows and are exhausted and want to go back to the hotel and sleep because you’re leaving early in the morning.

PLAYBOY: When you do stand-up, are you annoyed if people in the audience yell out requests?

KROLL: I just let them get it out of their system. I’m like, “Everybody, let’s all scream things that we want and think we like. Let it all out. Let the poison out.” I let them have that moment, and then they tend to settle down. If that doesn’t work, there’s a thing I learned from Aziz Ansari, who I think learned it from Louis C.K. Once you finish your set, you come out for an encore and it’s all about answering questions or taking requests. Some people really want to hear certain jokes. They want to hear it live like they heard it on an album or a special or a TV show.