Simon Amstell on Finding Fault with the World in His New Standup Show ‘To Be Free’

Simon Amstell - To Be Free - Color 3 - Photo Credit Kurtiss LloydLucky for us, British comic Simon Amstell is becoming a mainstay of the US standup scene. He toured the States in 2012 with his show Numb, a soul-baring hour focused on his own insecurities and over-active neuroses. He’s since popped up twice on The Late Show with David Letterman, and more recently on The Tonight Show and Conan. In April, he returns to our shores with his new show, To Be Free. I got the chance to catch up with him recently about moving beyond depression, the stress of late night spots, and enjoying his work in the US.

We talked a few years ago when you had just started your residency of Numb in New York. How was the rest of your time in the States?

It was good. It was two months of being at the same place, doing the show every night. The audience built every night and by the end, they were all squeezed in and sitting on the stairs, and it was all very exciting.

Have you found that doing standup in the US has influenced your style?

Um, noo? [Laughs] Not specifically that. There’s a freedom to being new. Just not being in England has meant that I’m more comfortable doing this sort of thing, whereas in the country that I live most of the time, I feel a bit awkward doing interviews because they feel a bit gratuitous and like the same ground gets covered quite a lot, whereas in a new place I feel like it seems appropriate to be introducing myself people who don’t know who I am yet. My career has been a mixture of standup comedy, television hosting, television writing, and acting, whereas here I feel like I’m sort of here as a standup comedian more than anything else at the moment, and it means that I end up talking about the material more. There’s a freedom of just being new in place, no matter what that place is. And luckily, you speak English here, so it’s handy.

You’ve been touring this show around the UK. If somebody’s seen you before, what can they expect for this show?

It’s still deeply personal and horrifically honest and all those things. It’s still somebody seeking truth and peace and joy and all those things. However, the show Numb was called Numb because it was about my inability to feel anything. It was about depression, really. And this show really is about having overcome depression through a couple of years of psychotherapy and a trip to Peru drinking ayahuasca, feeling like I would then be completely free and full of consistent, unwavering joy and then things still popping up that block that freedom, whether that’s my own insecurities or the fears of the culture that I’m in. I suppose this show is a bit less sad. Some reviewers have suggested it’s more outward looking, that I’m not so self involved as I was in the previous show, but I don’t know, to me it still feels quite self-involved. [Laughs]

I had noticed that in a few of the reviews, and I was wondering if that was a conscious choice?

In the last show, I ended up writing something about seeing the present time from the perspective of a better future, and wherever that came from, I quite liked the social commentary that that premise gave me, and I quite liked saying some things that weren’t necessarily just about my own psychological issues. But also, once you get over your own depression, there’s time, there’s space to look at everything around you. You’re not entirely wrapped up in yourself, and so other things pop up just naturally, I suppose. So in the new show, there’s a little bit more stuff about animals and the horrific way we treat other animals on this planet, there’s a bit more social critique than there used to be, but that’s not conscious, that’s just because I’m not as depressed as I was. [Laughs]

That’s great.

Yeah, that’s it really. But then it’s annoying. Because once you’ve done so much work on yourself and you’ve finally come to a place where you feel at ease, and like somebody who could exist as a human being in the world, then to sort of look at the world and have it not be completely ideal, is really frustrating. I’ve felt like I’ve been on a long journey to feel okay in the world, and it turns out the world isn’t ideal. It wasn’t just me.

You’ve done a lot of late night spots here in the last few years.

Yeah, they told me to.

Do you enjoy doing them?

No! [Laughs] Well, I really enjoy the relief afterwards when it’s done. And actually the second Letterman I did, I think I enjoyed. The first one was too terrifying. I find them quite stressful. I’m used to doing long shows; I’ve had to learn a different way of pacing the material specifically for those kind of late night spots. It really isn’t where I’m most at ease. I mean, I’m thrilled to be anywhere near the David Letterman show, that’s exciting for me, and I just did The Tonight Show, and then Conan.

I just did The Tonight Show, and I’d figured out what I wanted to say, and as soon as I got out there, the words started coming out of my mouth, and as I’m saying the words, in my head, all I keep thinking, “Oh God, I’m here. This is happening right now. Oh no! Oh no, this is happening! Quick, just keep saying the words, let’s hope they all just keep coming out of my mouth.” And then I thought, “Oh, you really sound like your mum. Why do you sound like your mother here? Maybe that’s okay, maybe just keep going. No, you don’t want to sound like your mother on American television. Maybe try and change your voice.” [Laughs] So there’s like a lot going on during this moment. Once you’re there, you just have to keep going for the four and a half to five minutes. Like, even if you do horribly, that will still be what is seen on the television later that night, so for somebody’s who’s a bit of a control freak and a perfectionist, the whole system is a bit bewildering.

But I think I appreciate it as a right of passage in terms of becoming a standup who can tour in America. I watch all the clips on YouTube of Seinfeld’s first Tonight Show and Roseanne, and I’m into those stories of Johnny Carson putting his thumb up and welcoming whoever the person who has done well onto the sofa. It’s quite a fun thing to be part of that bit of American culture, for a moment. But I find the whole thing terrifying, and when I finished the last one on The Tonight Show, that night, just thought, I don’t know how many more of those I can do. It’s a bit much.

And then to be doing two in two weeks — that’s a lot.

Yeah, the Conan was last minute. I was almost on the plane to New York when they said they want you on Conan, and I said, “[Sigh] Okay, then! Okay, I’m sure I can figure something out. No problem!” Having less time to think about it has actually made it a bit easier, I think. Because in the end, it’s four and a half minutes of being funny, and my job is to be a funny standup comedian, so this shouldn’t be too much. It shouldn’t be as big a deal, but I think because of the story around these, because of everything I was talking about before ­– basically it’s just walking out and telling some jokes and people laughing and then going home and having a cake. That’s all it is really.

We talked last time about trying to break into America, and I wondered what your goals are these days as far as establishing yourself in US?

What’s the deal now, I don’t know. The show To Be Free is about how I think I would be completely free in my life if I don’t have this terrible need to be loved and thought of as special and brilliant. The show is about this problem, the idea that I would be fine if I didn’t need so much attention, and not just attention from people in the country that I live in anymore, I also need it from American strangers. I talk about being at Theatre 80 and I talk about doing this residency, and it should have just been pure joy. I was in New York for two months doing a show that I’d written, and because it was the first time we were really making some sort of push to have people know who I am more than they currently do in America, the time I spent there became about that, and that thought, all that ambition, all that ego, drove me a little crazy. Somebody said to me, “You’re doing a show” — this is a joke now, in the show — “You’re doing a show in New York, people are coming to see a show you’ve written every night. If you’re not happy now, you’ll never be happy.” And I thought, “Well, I’ll never be happy.”

But having written all that stuff out of me, I now am living by this thing of really just enjoying each bit of it, and really enjoying being the new boy. I think that’s a really fun bit of this whole journey. I’m quite enjoying it. And as long as there’s a trajectory where everything turns out alright in the end, which, you know, I feel like it might, it’s great. It’s great. I think a couple of years ago, I was in a rush for something, and I don’t even know what that would have been, but for something to happen that meant that I was officially validated as an international comedian person. And now I’m quite enjoying each first thing. I’m enjoying the first Letterman and the first Tonight Show and the first Conan, but it’s all quite exciting. Yeah, I think that’s where I am.

Simon Amstell will be performing “To Be Free” in New York, Los Angeles, Chicago, and Austin in April. He can be found on Twitter at @SimonAmstell

Elise Czajkowski is a freelance comedy journalist/critic type person in New York City. She’s sporadically tweets at @EliseCz.

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