In 11 Questions, The A.V. Club asks interesting people 11 interesting questions—and then asks them to suggest one for our next interviewee.

Simon Amstell is a British comedian and actor who’s best known for making celebrities a bit uncomfortable as host of Never Mind The Buzzcocks, a comedy-quiz-panel show. His sense of humor is very dry and British in all the best ways, which might explain why he hasn’t made much of a splash in America yet. (Even a hilariously awkward appearance on The View a couple of years ago didn’t end up elevating him to household-name status, as it probably should have.) Amstell is back in the States this month for a series of stand-up shows—his “To Be Free” tour—and he’s pretty great at converting strangers into fans with the sheer force of his comedic will. (And a huge, infectious laugh.) Tour dates, including stops in New York, Chicago, L.A., Denver, and Austin, can be found right here.

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1. What’s the worst job you’ve ever had?

Simon Amstell: While I was doing my A-levels… Do you have A-levels in America?

The A.V. Club: No. How old are you when you’re doing A-levels?

SA: Between 16 and 18. What would you call that, high school? I was convinced by my evil stepfather that it would be important for me to have a part-time job. I went to work at the supermarket Tesco for three months. I was a checkout person. I didn’t feel like I was connecting with anybody in any kind of profound, human way. And I got told off for not smiling enough. One day I just sort of stopped going.

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AVC: Did you ever try to connect with the customers?

SA: No, it may have been my fault! It just felt like you were part of the checkout machine, like you weren’t a person. I’m such a joyful, brilliant weirdo that to not be able to express that because people are in a rush seems a shame.

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AVC: And now you’ve probably been replaced by an actual machine.

SA: That’s better! At least there are less human beings being used. [Laughs.] I think it’s good to be replaced by a machine if you’re already a machine.

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AVC: When you go to the grocery store, do you go to the person or the self-checkout?

SA: I look at the person and if they look like I used to look, then I go to the machine. But if they look they might be quite fun, then I go to the person. I don’t really know how to use those things confidently. Someone always has to come over and help you—you’re like a lost idiot!

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2. When did you first feel successful?

SA: I got my first job in television when I was 18, on the kids’ cable channel Nickelodeon, introducing the Rugrats and other programs. It was really thrilling. All I ever wanted, from maybe the age of 13, was to be on television. I was very excited by all the paraphernalia, like the earpiece and the microphone that got clipped on your sweater. And having fun with a crew and all that, I really enjoyed that. I had been pretending to be hosting a TV show in my bedroom since the age of 13, so to actually be on television doing that, and given money… That to me felt like something had really happened.

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AVC: Did the fake show in your bedroom have a name?

SA: I used to love this show called The Big Breakfast, which was this anarchic morning show aimed at young people, where you saw all the crew, and the cameras were handheld. It was all set in a real house, and the different segments of the show would be happening in different rooms—there’d be an interview in a bedroom on a bed, or some other some other thing happening in the living room. I pretended that I was hosting that show in my bedroom.

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The main host was a guy called Chris Evans, and he ended up having his own production company and making other TV shows. When I turned 17, I ended up doing work experience with his production company. I met him briefly, and it was maybe the biggest thrill of my life up until that point. And I’ve seen him since, having sort of attained some peculiar status myself, and I tell him—I think it’s going to be very meaningful to him—I say, “You were my hero!” And he looks at me like, so what, it’s not of interest to him. [Laughs.] I feel like he should hug me! He should say, “I’m so glad I made a difference!” He just looks at me.

3. If you were a supervillain, what would your master plan be?

SA: So it would have to be villainous? Evil?

AVC: People have answered this in less-than-evil ways.

SA: Oh my goodness. [Long pause.] I’d say that people weren’t allowed to have… There’s got to be a way of phrasing this that isn’t totally insane. I think I’d ban all flags and make it a crime to anyone to have a sense of collective identity. I think that would sound harsh to people who like flags and who felt proud of where they come from, but ultimately it would lead to a sense of unity and compassion and love. It’s not villainous!

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AVC: Some people might think you’re a villain for that, and call you a faceless communist.

SA: Right, okay. But I would say, “I have no flag. I have no sense of identity connected to communism. Because I’ve banned it! I’ve banned all of these words.” And then to prove it, I would squat on the floor that I was standing, and I would shit on the floor, and I would say, “We are all the same.” [Laughs.] There you go.

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4. What were you like as a kid?

SA: I was very shy, but then when I went to a Saturday morning drama club, I became quite… What’s the opposite of introverted?

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AVC: Extroverted.

SA: Ha! I became incredibly extroverted. That doesn’t feel like a word.

AVC: It is!

SA: Extroverted. But only if I was standing on a stage or in front of a camera. I was still very shy in real-life situations, but performing I became super-confident. So I felt very safe when I was performing, but still a bit anxious when I wasn’t.

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AVC: Is that still true at all?

SA: A little bit. I’m better now than I used to be. But I still feel the most free when I’m onstage doing the show that I’ve come up with.

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5. Who was your celebrity crush when you were younger?

SA: I’ve been talking about him today, actually. Leonardo DiCaprio was probably the key figure for me. I was just watching Woody Allen’s Celebrity yesterday, and his hair is the most beautiful thing that maybe has ever been captured on film. It’s so effortless and the movement of it is… Even the greatest wigmaker of our time could not re-create the subtle, effortless movement of Leonardo DiCaprio’s hair in that time period. I would go to the video shop near me and secretly rent every Leonardo DiCaprio film that could be rented at that time. This was a time of intense sexual confusion for me, so it wasn’t just having a crush—it was a major crisis in my life.

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AVC: About how old were you?

SA: It was probably anything from 14 or 15, I suppose. Good God, when Romeo + Juliet came out, and he’s looking at Juliet through that fish tank… And again, the hair falling over his eyes, through water, through fish! [Laughs.] Nothing could be better than Leonardo DiCaprio’s face, hair falling over his face, and then you’ve got some fish swimming by as well! That Baz Luhrmann knew what he was doing.

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AVC: Does that crush continue today?

SA: He’s not a boy anymore. He’s not the angelic troubled young man that he used to play. He’s now sometimes a quite beardy, big man. If we met I don’t know quite what would happen. There was some real sadness watching Celebrity yesterday, because film does this incredible thing where it stops time for a moment. He’s right there, moving, speaking, hair flowing, but that’s not actually there anymore. It’s gone now. There’s something about film, and I think it’s to do with that we all get old and die. Apart from telling stories, that’s one of the reasons that we love it. It captures hair. [Laughs.] It captures hair at its peak.

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AVC: You picked two bad-boy roles.

SA: He is a naughty boy in both of those. In Romeo + Juliet it’s for love; in Celebrity it’s ego and power. But yeah, he’s naughty. Good God, though. Oh my goodness. You brought it all back to me!

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6. If you had entrance music, what would it be?

SA: When I did the Letterman show, they ask you what music you want to come on to, and I chose, “I Like To Be In America” from West Side Story.

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AVC: Do you have anything playing before you do stand-up?

SA: I have a lot of Michael Jackson as people are walking in. The show is called “To Be Free,” so people leave hearing Nina Simone’s “What It Feels To Be Free.” [“I Wish I Knew How It Would Feel To Be Free.” –ed.]

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What about “Part Of Your World” from The Little Mermaid? [Laughs.] That song’s all about wanting to be where the people are. It’s about wanting to connect and be somebody who can exist in the world, on land, and breathe easily. It’s an interesting song. She has to give up her voice in order to attain that wish. And that’s what my show, “To Be Free,” is kind of about. What do you have to give away in order to be accepted in the culture you’re in? How much of yourself can you actually be? Are we really free? All that sort of stuff. That’s all covered in The Little Mermaid.

7. What have you done so far today?

SA: I edited together a kind of mood reel for a film I’m trying to make. And then I had a meeting with a theater producer and an ex-lover who now works for that theater producer, which was a lot of fun.

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AVC: Was that sarcasm? Was it an awkward meeting?

SA: Only because I made it awkward. He now works for her, and I hadn’t seen him for a while. I just kept saying, “Have you still got that great stomach?” And he’s like, “This is my boss!” It was the best bit of him! It was a fun lunch. And then a comedian friend of mine came around and we tried to write something funny that I don’t want to give away yet.

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AVC: Did you have some success?

SA: It was fun, and we wrote down some things on Post-it notes. There’s some Post-it notes on the wall, so I think that means that something must have happened.

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8. Have you ever been mistaken for another celebrity?

SA: I may have a similar face to Jesse Eisenberg, or we might just both be Jews. People have asked me if I’m Jesse Eisenberg, but I think all that’s happened is that they’ve seen a Jew and become confused. [Laughs.]

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9. If you had to find another line of work, what would you put on your resume?

SA: I could put down “untrained, unqualified psychotherapist.” I could pretend to help people, you know? I could give people the impression that I was listening and ultimately helping. There’s no evidence that that would actually happen, but I could probably get away with it.

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10. Do you collect anything?

SA: No! There used to be some scrapbooks… Should I be collecting something? What do you collect?

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AVC: Nothing, really. I used to collect records. People tend to be surprised that they don’t collect things.

SA: I occasionally buy things. Can I just say products?

AVC: You have a sort of loose collection of everything you own.

SA: Yeah.

11. What would your last meal be? You’re vegan, right?

SA: Yes. Oh my goodness. There’s a restaurant in London called Mildreds, and they do a very good vegan burger. They do a burger of the day, and it always tastes like the same burger, but they claim there are different things in it each day. That’s good, and probably quite comforting. I suppose if I knew I was about to die, it’d be nice to have something comforting. I’d probably be too panicked to eat. What would they say? “We’re gonna kill you in an hour. Do you fancy anything to eat?” I’d say, “I’m not very hungry; maybe we should discuss this whole murder that’s about to take place.”

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Bonus question from Simon Pegg…

SA: Did he know it was for me?

AVC: No. Here it is: Has there ever been a point in your career where you thought seriously about doing something else for a living?

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SA: You sure he didn’t know it was me? [Laughs.] Not something else. But about once a week I think about going and living in a cave and meditating instead. I think that would be a more peaceful life, where my spiritual journey was not interrupted by egomania so regularly. But I don’t think there’s anything else. What I do is quite varied. If I was only doing stand-up, I think I’d feel like I couldn’t possibly get on another train or plane to do this show again. But because there are other things going on at the same time, I never feel too upset about doing one thing. Apart from that once a week moment where I feel like I probably should retire.

AVC: Will you go off to the cave in 10 years?

SA: The truth is I’d be very bored, and it’d be unbearable. I’d think, “I had a really nice flat, what am I doing in this cave?” But it’s good to have, if only just theoretically, an escape route, so that what you’re doing doesn’t feel too important, which it isn’t really. The whole thing is nonsense, and then we die, so it’s useful to have an idea of something else that could be the thing that you do instead. I don’t know. I’ve lost the will to live. [Laughs.] I’ve got nothing left; I think I need some iron.

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AVC: What would you like to ask the next person?

SA: Oh God. Some version of “Who are you really? What’s really going on? What are you hiding?” Those three questions, is that okay? You can ask that to anyone.

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