Simon Amstell is a comedian and television personality who's honed his craft over years in the public eye. Stateside, Amstell is mostly recognized for his standup, having performed sets on Conan, The Tonight Show and the Late Show with David Letterman. In his native U.K., however, Amstell is a household name who rose to prominence as a TV presenter on shows like Popworld and Never Mind the Buzzcocks before writing and starring in the BBC sitcom Grandma's House. After winning worldwide acclaim for his last special, 2013's Numb, Amstell is back on the road with a new hour, preparing to make his debut in the Mile High City at the Comedy Works on Tuesday, April 21. In advance of that gig, Westword caught up with Amstell to discuss performing overseas, getting high in Denver and his new hour of comedy, "To Be Free."

Westword: How long have you been in the States?

Simon Amstell: I just got to New York. I’ve just been here for a day; after a few shows here I’ll start flying all over the place.

Where else are you stopping besides New York and Denver?

I think that there are another five or six this time. Later on in the year, I’ll pop back and do another few.

How do you like performing in the States?

I quite like America. I tend to create the show in London, do a tour of the U.K., and then come to America. Because you people speak English. I don’t think I’ve been to Denver before.

Never?

No. Is it nice?

Sure. It’s usually a lovely time of the year to visit.

What should I do when I’m in Denver?

A lot of tourists come here for the legal weed. I don’t know what your proclivities are there, but it seems to be quite the attraction.

Okay, I’ll have some. You got some? I’ll take it.

A good number of our citizenry always have weed on them, all the time. Chances are it won’t take long if you ask around. Or you could stop by the recreational stores and buy some yourself for the novelty of it.

Okay, that’s great news.

There are also the mountains; those are a pretty big deal. Let's see; we have a great parks system and museums. Denver's a metropolis that's still forging its identity.

Pity I’m only there for one day and one night then. I’ll do one of those things. Probably just the drugs.

So, American audiences don’t necessarily recognize you as much for being a TV presenter, the way they would in the U.K. Does that help with standup?

Even in the U.K. I feel like I’m now most recognized for comedy. Because after all the presenting stuff, I ended up writing and starring in a sitcom, and I’ve done two standup tours since that sitcom was on TV. I suppose it’s more just pure standup with American audiences than in the U.K., yeah.

Your special Numb came out two years ago. Are you working out new material for another special?

Yeah, this new show is called “To Be Free” and it’s a whole new hour, a completely different show. Every sentence is a new one.

Do you tend to build an entire cohesive hour around a theme like that instead of joke by joke?

Yeah, I’m not interested in jokes. I’m only interested in transforming the toxic nonsense within me into something funny. If it isn’t therapeutic in that way, then it all feels a bit gratuitous. This new show doesn’t start as a cohesive show; it starts with me going onstage in front of about fifty people who haven’t paid too much, who’ve been told that they’re seeing a work-in-progress show. And I just sort of keep talking until something funny or interesting happens. Then I tend to write down whatever that thing was and repeat it, and then keep building on it. Then later, a theme builds up. So with this show, all the stories I was telling seemed to be about freedom, or a lack of freedom. Do I lack freedom because of my own insecurities, or the fears of the culture I’m in? So it seems, in the end, that’s what the show is ultimately about. But I had no idea that’s what it would be about when I first started saying all these things out loud in front of people. 

That’s such an interesting method. Just sort of casting around in the dark for a theme like that seems nerve-wracking.

I don’t think you can decide what show you’re going to write. I don’t think you can decide what it’s about. It wasn’t really anything to do with me. If I’d have made the decision to do a show about some particular thing, I think it’d probably stink. You know?

People often don’t want their comedians being too strident. The guy who’s “up there to make a point, goddamn it!” —that guy isn’t much fun to watch.

I find that really hard. There’s a bit in this show about eating animals and it’s the most tricky bit of the show. Because even though I’m definitely right, and eating animals is a horrific thing to be doing, it’s a very tricky bit of standup to make funny. Now, it’s very funny, but it took a long time to get there.

You’re throwing down the gauntlet whenever you make a statement someone might disagree with.

A little bit of a gauntlet, yeah. Usually I’m quite funny when I’m the one who’s the idiot, so when I hit on something that I think I’m right about, it’s trickier for me. I’m much funnier when I definitely know I’m wrong.

People might get extra sensitive about a vegetarianism joke because that makes them question their own habits.

I suppose that’s true.

Ok, for example. I told a joke about how I quit smoking cigarettes and got booed by all the smokers.

That’s very funny that you got booed. That’s really funny. I hope it didn’t discourage you.

Nope, 91 days smoke-free. I have an iphone app that counts the days. It’s been a struggle, which is probably why I’m talking about it with a stranger.

Wow, congratulations. One day at time. I didn’t know you were a standup as well, I just assumed you were just some journalist lunatic.

That’s sort of a cool thing about our newspaper. A lot of people writing about the music scene for our paper have been in bands, so there’s that authenticity. We do try to know who’s good and who’s full of shit when we can.

Okay, good. Who was the last comedian you spoke to?

Marlon Wayans.

Oh yes. He’s got all those brothers.

Anyway, so you’ll be at Comedy Works. Do you prefer to perform in bigger theaters or the sort of low-ceiling, two-drink-minimum type of classic comedy club?

I like the low ceilings. People forming a sort of wall around you is good. The seats not being too comfortable is good.

The audience are seated very close together, so they do become this wall of supportive laughter. It’s the best. So, the first few times you did comedy, how did you approach it? Did you have some jokes written out beforehand?

The first standup gig I did was as a thirteen-year-old in the annual show for my drama club. How did I approach it? I suppose I’d seen a lot of standup comedy on TV, and I think I liked the idea of being one of those standup comedians because I suppose they looked quite free. Also quite peculiar. They used to show clips from the Montreal Just For Laughs Festival on Channel Four late at night, and I’d stay up to watch. I don’t remember the names, just that they were all fairly wacky comedians. I remember there was a guy with pieces of card, with the words “this” and “that” written on them. And he’d hold up the card that said “this” and say to the audience “Would you look at ‘this?’ Have you even seen anything like ‘this?’” Then he’d hold up the other card and say “What about ‘that?’ I bet you weren’t expecting ‘that!’” And I thought it was amazing, and I think at thirteen years old I just stole his act. And I had a really fun time. The rest of the show was all ballet and serious dramatic performances, so it might have been a relief for the audience to see a funny child with his bits of paper.

It' a funny inversion of the paradigm of a standup as a grizzled, middle-aged man. To see a funny kid instead.

And quite peculiar. I'm really very grateful to that funny kid that I was. He knew how to get things done. So that was the first time I did standup, and I was quite a hit locally, so I was invited to perform at some charity events at the local theater. I also entered these standup competitions. One of them was the BBC New Comedy Awards, which I did quite well in, and that led to meetings with people who were interviewing for presenters. When I was older I ended up getting a job at a kids' cable channel that led me getting sacked for being a bit sarcastic, for being too mean to the pop stars. Then there was a show on Channel Four that turned quite irreverent because they hired two people who liked being mean to pop stars.  

Was that Never Mind the Buzzcocks?

No, that was before that. I honed my craft on a show called Popworld that ran for five years. It's weird; the only time I end up talking about this sort of thing is during interviews. Talking about your whole career and its beginnings. Generally, I just sort of keep going, I suppose.

Now that you've developed a fan base, how do you manage their expectations with your new material?

I try out the material in a place where I'm allowed to fail. That's the point of doing these shows in front of fifty people who paid five pounds each. I'm allowed to be really unfunny for an hour. If I am funny, it's like a bonus for the people. At that point, it's not really a risk. The real risk would be to play it safe. Standup comedy is one of the few places left where you can really say whatever you want. You have license to express your whole self. I say things onstage that I feel like I can't say as much in everyday situations. Also, that's what the people seeing you really want, so the trick is holding back and not saying what's in you at the time. That's the bigger danger, holding something back because you think it's going to be a bit upsetting for people. I mean, that's standup comedy, right?

That's the one privilege comedians get that few other people do, which is probably ket to its appeal. Otherwise, the life of a standup isn't very glamorous. Lots of solitude, lots of surly drunks staring you down. Do you have any particularly memorable bad gigs, where it was just a poor match of audience and performer?

It's tough because on a tour, the people have generally come to see me. There was some sort of charity awards show event for companies that had invented things or provided various services for people with disabilities. A typical award would go to like, a car company that made their vehicles more wheel-chair accessible or something like that. This is maybe ten years ago. So I was brought on to do some standup afterwards, but the host of the awards ceremony didn't introduce me as a standup comedian, they just said my name. The audience were of an age that they weren't necessarily my demographic so I don't think they knew what I was doing there. At the time, I had some material that I thought was quite relevant about Mattel bringing out a Barbie who was in a wheelchair. So I started doing these jokes about wheelchair Barbie and the points where the crowd would normally laugh there was this silence and confusion in the room. So I started to get a bit tense, and I think, "Okay, if I start getting tense, they'll start getting tense, so let's get off the subject. It's not quite working even if it feels very relevant to the situation." So then I started talking about my relationships, or my sex life or something and it's still silent, but now there's much more confusion and maybe even some anger in the room. I think what happened was that there was no sense I was a comedian. They all thought I was brought on to give a speech about disabilities, so when I started talking in this peculiar way about Barbies and the people I was having sex with they must have been thinking, "What? This isn't a very good speech! Why is he doing this?" So I started feeling sort of worn, but I had a fifteen-minute spot, so I thought I'd better keep going. So I'm rambling on, hoping for the best and not understanding why I'm not connecting with these people. And then a note comes from the back of the room, and I read it to myself. It says, "We think it may be a bit late for standup. Perhaps bring on the band." No problem; I was happy for the escape route. So I thought I'd read the note aloud, it'll be kind of self-deprecating and people will laugh at this note I've been given. There will be laughter and applause and then I can finally get off the stage. So I read out the note: still silence! They must have been thinking, "what do you mean, standup? There's a band?" So yeah, that might be the worst thing that ever happened to me.

Sending a bombing comedian a polite note is so British.

It is polite. Their way of saying, "It's not your fault. It's just a bit late." 

So, you do talk about your personal life a lot onstage. The people you're having sex with, or your experiments with ayahuasca. When did you decide to take that bent with your act?

I didn't really. I think that I maybe just didn't know what else to talk about other than what was going on with me in my life. I think it's really personal because it's a way of exposing anything that I think is shameful or embarrassing. It's shining a bright light on this thing about myself that I can't stand. And once it's out there, creating laughter and joy, I don't hate myself as much anymore. I feel like if I was really perverted and really horrific as a human being, they wouldn't be laughing. They'd be looking at me like maybe the authorities ought to be called. In their laughter I hear them thinking, "That's like us. What you've expressed is something we can't say out loud. We've also done those disgusting things, so thank you for saying that." And then I feel less alone. I feel like less of a weirdo.

Simon Amstell will perform at 8 p.m. Tuesday, April 21. Tickets are $15 on the Comedy Works website. Unlike with most Comedy Works shows, food and beverage service will cease once the show starts and Amstell will have no opening act.

Follow Byron Graham on twitter @ByronFG for more mildly amusing sequences of words.