The Sunday Interview: Will Cleveland

Welcome to the wonderful world of Mr. William Cleveland. He’s not from Cleveland. He’s from Arkansas. But he cut his comedy teeth on the mean streets of Chelsea and Brooklyn, NYC. Not long ago, Will migrated down to Austin and quickly got to work. In short order, Will has become a staple on the Austin comedy scene. He improvises, he writes, he directs. He does a little bit of everything, and he does a lot of it. Most nights, you can find will at one of Austin’s many comedy venues, and he’s likely to give you a hearty handshake and huge smile. The guy is just a world-class comedy robot who knows more about what makes something funny than I know about the battle of Gettysburg. Which is saying something, because I watched a documentary about Gettysburg the other night.

This is Will Cleveland. He wants to make you laugh.

This is Will Cleveland. He wants to make you laugh.

Will Cleveland

Age: 33

Years doing improv: 
I’ve been a comedic performer as long as I can remember. My brothers will tell you that I was always being a ham and seeking validation of whether or not something I had just done was funny. (Trust me, that sentence is going to kill with my brothers.)

I did a form of improv in high school that was essentially quick sketch writing because they would give you a scenario, then me and my partner would go away for 30 minutes and come back and do a scene. After a year of doing theatre in college, I got a job touring as an actor in a children’s theatre (Theatre IV) and continued doing Summer Stock and regional theatre in the south until I moved to NYC in 2008. That’s when I started taking classes at Upright Citizens Brigade.

So the answer is about seven years of doing improv, or since the end of the Bush 43 administration.

Troupes and shows involved in now:

  • Double Tap
  • Real Live Men
  • The People in This Room
  • The USA
  • Stool Pigeon

Web + @Will_Cleveland

You’re new to Austin — probably the newest transplant we’ve interviewed on But you quickly made you presence felt. It seems like you are doing all sorts of projects all over town. Is that your natural state? Or was it strategic to get so involved as a “new guy” to a new city’s comedy scene? Any advice to other “new guys” out there?
It was probably mostly out of habit. In NYC, I was going to a meeting, show, rehearsal, class, or film shoot all the time if I wasn’t working at my job. I also didn’t know anyone here so I wanted to make friends. The hardest part about moving here was leaving my community of people, particularly the UCB. So I suppose I was coping with that in a way.Advice would be to check out the websites of theaters for drop-in workshops since you probably don’t want to start with Improv 101 if you’ve had training in Chicago, NY, or LA. Surely there’s an area you feel needs work and there’s a workshop in Austin for you. You meet great people and get in some solid practice.Your mustache. Discuss.
I moved to Brooklyn in the height of mustache irony. The ‘stache had transcended the pedophile stereotype and entered into a new era of stylistic reference. We live in an interesting time of fashion. Nothing is done without reference to not just one era, but all eras. I saw a guy dressed as a 1950s-style milk man in Bushwick once and I didn’t bat an eye. He was just doing his thing!So you’ve got young hipsters growing ironic mustaches saying, “Ha! I look like a pedophile” and you’ve got brawny older guys growing them saying “Call me a pedophile, motherfucker, I dare you!”I have a real baby face and so I thought it would age me a little. I was working as a bartender late nights and we didn’t have security, so I thought if I looked a little older, people would be less tempted to be an asshole. Another reason is this:I started coming around the UCB during Bobby Moynihan’s first year as a featured player on SNL. I was getting mistaken for him a lot because he was there the several years before, and let’s face it, we do look an awful lot alike. I should’ve just lost 35 pounds, but anyway, I was getting mistaken for him a lot less after (the ‘stache).

My partner, Amber, likes it and people compliment it, so it stays for now.

You’ve taken your fair share of classes and workshops. Which instructor stands out to you? What did you learn from her or him?
The thing that stands out most about all of my UCB teachers is how disciplined they all were. There seemed to be a harmonious mix of “we’re here to have fun” and “focus, goddam you” in all of my classes and coaching sessions.

Gil Ozeri was my 101 teacher, and he demanded more out of us than just truthful commitment and yes, and. Maybe it was for his own enjoyment but he wanted to see us playing with “game” by the third or fourth class, which is what the UCB teaches in 201. It made our end-of-class show a lot better than it could have been. I imagine having a pretty good show your first time up on the UCB stage makes a big difference in whether you want to continue. We did, and I was hooked.

Will is the one on the right.

Will is the one on the right.

You’re very busy, very driven. Are you working toward a grand show business dream, or do you keep your projects more short-term?
Welcome to my brain space every morning!

I am working towards a grand show business dream — thanks for asking — but I’m not sure yet what it is. I wish I could see around that corner. I just know I want to do good and fight evil and that I want to be a working actor for the rest of my life.

But let’s talk about Bobby Moynihan again for just a minute: I moved to NYC to pursue a boyhood dream of being on SNL and when I saw Bobby on his first episode, I knew immediately that that dream was over. I wasn’t bitter or anything because Bobby is awesome. I was just thinking (as a producer) that “I wouldn’t hire Will, I’ve already got a guy like that.” But I was still a writer, so there was that.

So I started focusing on sketch more. I eventually got selected to be on a UCB video sketch team. They called them Beta Teams at the time. My role was producer, but I was writing constantly for the group. I wrote one or two scripts hoping to get greenlit and cast Bobby in the lead role during the summer when SNL was on break. One sketch I wrote was pending green light based on getting him cast. Scheduling never panned out, but I’m very proud of what I was able to accomplish while at UCBComedy.

Just before moving here, Amber scored tickets to Marc Maron’s special taping at La Poussin Rouge which was released as Thinky Pain. John Mulaney’s special, New in Town, came out a few months before, and I watched them both on Netflix just a few days apart. I’m sitting on the front row of Thinky Pain. Bobby is sitting on the front row of New in Town. John Mulaney, Bobby, and I are roughly around the same age. Maron is 50 and has had a long career of doing comedy, yet his commercial success can be mapped to the taking-off of his podcast in recent years. So Mulaney’s got a sitcom, and Maron’s got a sitcom. What I’m saying is, I’m in this for the long haul. Hosting SNL is still on the table.

Who’s the funniest person you’ve personally met?
Oh god, tough question! My friend Ryan Healy from NYC might be. He’s not a comedian and has never stepped foot inside an improv class. He’s just very smart and does great impressions.

It’s hard for me to answer this question and not also think of my friend Taylor Moore. Everyone should listen to his and Ryan Williams’ podcast, Ten Ideas.

At any given moment, Achilles Stamatelaky might be the funniest person on the planet who’s not famous. Follow him @astamate.

You’ve said that Ben Schwartz is probably your favorite improviser to watch. Why?
Because he’s having the time of his life when he’s on stage and you can see that. I saw Hot Sauce (Schwartz, Gil Ozeri, Adam Pally) at a DCM a few years ago and they just deliver some of the hardest, fastest, and wittiest scene work, which is a style I love watching and strive to play. High-octane/maximum-laughs.

Schwartz is great, but I think Scott Adsit is my favorite improvisor to watch if I’m being totally honest. That guy can make you cry as quick as he can make you laugh. I’ve seen him at Assscat some, but mostly I’ve seen him perform in Duos (Adsit & (Chirstina) Gausas and John (Lutz) & Scott). I would go see him every chance I got. I saw Schwartz the one time.

You play mostly at Austin’s northernmost (ColdTowne) and Austin’s southernmost (The Institution) improv theaters. Tell us your impressions of both.
Both theaters teach the Harold as the foundation of doing long-form improv shows, which is important to me coming from the UCB. The last teacher I had at UCB was Michael Delaney. It was a sketch class and I was in a bit of a rut with a piece I had written and he said to me, “Well, you do the Harold, don’tcha?”

He explained to me that doing the Harold was like yoga for comedy writers. I hadn’t done a Harold in over year at that point, so coming into this new city with several improv venues, I wanted to practice and perform the Harold more because I felt I hadn’t taken full advantage of that while at UCB.

Will loves America, which is one reason he plays with his troupe "The USA." Try to catch them around Austin soon. Highly recommended.

Will loves America, which is one reason he plays with his troupe “The USA.” Try to catch them around Austin soon. Highly recommended.

ColdTowne reminds me of the UCB theatre in Chelsea (NYC). It’s a little dirty and feels like you’re in a basement. The students are cool and funny and supportive. People hang out together at the bar after shows and there’s a very strong community that wants to see each other succeed and get better. They’re also the only space in town with shows seven nights a week, and I have mad respect for that.

The Institution Theater holds itself to a very high standard of show quality. Tom Booker’s experience is unmatched in this town, so any chance I have to work and learn with him and Asaf (Ronen) is an opportunity I feel very lucky to have. And playing with them both in the Rubber Room is a tremendous amount of fun. At the Institution, I think it’s a little more your own responsibility to get better and less team-based because there aren’t as many troupes being formed. However, the students have a constant cheerleader in Tom and the rest of the staff. The Institution is also the newest improv venue in town, and it’s looking like they are really starting to hit their stride. I’m excited to see the work coming out of there this year.

What’s something improvisers could do right now to get better at improv?
Read that (insert classic literature author here) book you’ve had on your shelf for six months after finding it in a “free take” box on the street or on campus. You picked it up and took it home because you knew it was something you should read, so get to it. I’m also guilty of this. For me it’s Zusak’s The Book Thief. I’ve had it since last summer and haven’t read it yet.

Why isn’t there more cross-over between the comedy disciplines — improv, writing, stand-up. I mean, there’s certainly some. But I’d venture that only a small percentage of folks do more than one thing very seriously.
I think it boils down to people who do improv want to have fun and perform, and people who are doing stand-up (and write) have something specific they want to say. Are they both conveying real life experience to an audience with the end goal of laughter? Yes.

Doing both regularly is something I struggle with. I touched on this before, but I basically stopped doing improv at UCB once I was placed on a sketch team, and when I’m involved in an improv show, I put other projects on hold and rarely perform stand-up. There are people like Mac Blake who are really good at both, but he’ll probably tell you too that when he was crushing it in the stand-up scene the last couple of years, he was probably only doing improv occasionally. They require different disciplines, that’s for sure, and people have various strengths and comfort levels.

I think that people who are serious about having a career in comedy should pursue stand-up. It’s the best way for industry people to take notice of the work that you’re doing. Not at first, but we’re in festival city, so there’s no excuse for you to not get some exposure eventually if you work hard. If improv is your only thing, the chances of getting seen are smaller. Improv is a great tool in commercial auditions, but if you want to pursue sitcoms, writing or acting, stand-ups have a better track record of success.

Also, what of acting classes and auditioning for plays? That’s important, so you need to do that too. Now, I think that people who are taking improv classes or doing open mics should be doing so to get better at improv and stand-up and that’s it. That’s the only mindset they should have. I’ve been guilty of “loving myself in the art” in the past and that’s the wrong approach.

What’s the hardest you’ve ever laughed?
I consider myself an extremely lucky person to laugh as hard and as often as I do.There’s a recent memory I have of just completely losing my shit:

I was performing at The New Movement and I had gotten there early to catch the show before. There was a class troupe followed by a house troupe. One of the students from the first troupe came into the theater with a bottle of wine that we was going to serve to his friends and drink during the second half of the show. He dropped the bottle during one of the scenes and it was loud. It scared me half to death and it took the players out of the scene for just a second, but they adjusted, making the sound a part of the scene. So it’s a funny scene and it’s working.

Meanwhile, there’s this guy quietly dealing with the bottle of wine he just shattered on the floor. There was this mix of still feeling scared by the sound, the scene being funny, and this guy cleaning up the mess — and I started laughing.

Now, I’m an audience member at a comedy show so that’s a good thing, but the scene starts to peter out and I’m laughing harder and harder and I start to think to myself I shouldn’t be laughing this hard, which makes me laugh even harder. I mean, I am losing it. I’m at full guffaw and the rest of the audience is pretty quiet.

I start to stifle it, and the next time the show gets a laugh, I let it all go and then excuse myself to the street until I can get it together. I wasn’t laughing at the kid who spilled the wine. I wasn’t laughing so much at the show. It was just the combination of things I was feeling.

I called my partner, Amber, once I got on the street to tell her about it and I couldn’t explain it to her without laughing. I was doubling over on the sidewalk, laughing as hard as I had ever laughed into a phone.

All in all it was about ten minutes of laughing non stop and nobody could even know what I was laughing at. I really love that feeling of getting tickled at something when it’s not one hundred percent appropriate to be laughing, which always makes me laugh even harder.

Also, doing just about any improv warm-up with Kirk Johnson is good for some utterly uncontrollable laughter.

Who’s an underrated performer or troupe in Austin?
Movie Riot isn’t sold out every single week which is baffling to me. There should be a line around the building.

Paul Normandin’s ability to play to the top of his intelligence is among the best I’ve seen. I see a lot of people play with only one foot in the scene and they end up breaking or second guessing.

If you wrote a book about improv, what would be the titles of the first three chapters?
1. No rules, only discipline.
2. Nice Corvette. Know how to change the oil?
3. Fun class. Where we goin’?

Anything you’d like to plug?
• Stool Pigeon – Thursdays in March at ColdTowne
• Play-by-Play – 3rd Saturdays at ColdTowne [Yours truly will be playing in this show on Feb. 21.]
• Intro to Video Sketch and Video Sketch Lab (Level 2) – enrolling soon at ColdTowne

What’s something that most people don’t know?
One of my acting influences is my uncle Jackie Stewart who is in several movies, one being Sling Blade as the lawn mower repair customer.

Will and his talented partner, Amber.

Will and his talented partner, Amber.


  1. Kenny Madison on February 16, 2015 at 12:39 pm

    Great interview. Great great interview.

    I had the pleasure of stumbling upon Mr. Cleveland at a restaurant once. We just happened to both be there. We ended up talking for about an hour about improv and comedy and all the boring parts. One of the most insightful, intelligent people I’ve talked with in this town.

    • Jason Pelker on February 16, 2015 at 1:19 pm

      Agreed! Will’s a great source of serious thinking about a funny business.

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