Crixeo: Emma Willmann Interview


"You'll Never Make It" & More Motivation from Comedian Emma Willmann

It’s no secret that the life of a standup comedian is tough. First, there’s the audience: a bunch of eyeballs staring up at you from cabaret seating, arms crossed, daring you to make them laugh. Then there’s the pressure. You’ve got to write fresh material that will kill, every time — and competition is fierce. Finally, there’s the lifestyle of late nights, bad food, constant travel and budding relationships that can slip through your fingers like sand. And even if you do become a success, the problems only increase. What’s next after the best joke you’ve ever written? How can you hit the gym when you already need to be in a million places at once? Why should you have to choose between a relationship and writing new material, the very lifeblood of your existence? What do people even find funny these days anyway? The struggle is very, very real. And not everyone can, or will, “make it.”

So why do it at all? Often a turn to comedy is an unexpected transition, and it’s not exactly the job parents are pushing their children toward. In many cases it may be the very last resort. It’s the feeling of “If I don’t love doing this, then I don’t know what I’ll do.” Yet at the same time that empty stage and open mic dare you to be yourself, to share your point of view and say what you came here to say. And sometimes you’re good enough to make that your career. At least that seems to be the case with Maine native and rising comedian Emma Willmann.

You may have read about her in the Boston GlobeElle Magazine or even TimeOut New York which named her one of the “Top 10 funniest women in NYC,” or perhaps you’ve heard her on Sirius XM Channel 99, where she hosts The Check Spot for Raw Dog Comedy. She toured with Louis C.K. and cohosts the weekly podcast Inside the Closet with Matteo Lane. But most likely you’ve caught her set on The Late Show with Stephen ColbertCrazy Ex-Girlfriends or Crashing (in a role chosen for her by Judd Apatow himself). Emma’s style of comedy? High-energy, quick-witted and upbeat without the side order of political commentary. She recommends her style to people looking to tune out for a minute. “Don’t watch me if you’re trying to think,” she insists.



But Emma isn’t alone in her quest for standup success. There are other comedians out there, up-and-coming or otherwise, who are also out in the trenches, trying to determine what works and what doesn’t. And the world is changing — fast! So I asked Emma if she had any advice for fellow artist entrepreneurs and standup comedians trying to make it in this crazy world. Here’s what she had to say:

How did you find yourself in standup comedy?

I was always thinking of ideas and at first thought I wanted to be in marketing, politics or music — which seems so scattered, but really it’s all about pushing something forward through words…being a part of creating some form of a reality bigger than yourself. And with comedy, it was like everything else had hit a wall. I’d never thought of standup before but had always used humor as a coping mechanism to deal with being a fat kid, dyslexic, gay — all that. Humor was the buffer. So when everything else crashed and burned, I kind of looked more inside for what I could create, and it was…myself!

What do you think is the role of a comedian in today’s society?

The role is to entertain, but it gets tricky because it’s also one of the last spots where people can say something totally uncensored. And if you make it funny, people will listen. The role is to entertain. I wouldn’t mandate it to be more than that, but I think if you really want to get somewhere, you’ve got to make people see your worldview, or at least laugh at it or relate for a little while.



How is standup comedy similar to or different from acting?

The main similarity is that you are putting on a show, so you know that there are so many things that go into it. And whatever the finished product is, it’s very far from whatever the work was that went into making it. That said, acting is a totally different muscle. It’s collaborative and more listening-oriented. It’s also softer. But I love acting because I love working with other people. And once you have gotten the part, the judgment and feedback are not that insane, real-time intensity of standup. So when I’m working on an acting thing — no matter how crazy the hours are — it still feels like a break because, in my experience, nothing is as intense as standup.

What do you think makes for a great comic? What benchmarks do you strive toward, and what other comics might you recommend to your audience?

I think — baseline — a great comic has fantastic insight, joke-writing and performance skills, and the ability to listen. After that, it’s pretty subjective. I personally adore when someone puts on a show. I love Katt Williams and Richard Jeni. Pacing around the stage and using voice inflection, for me personally, can really take something to another level. And if someone likes me, I think they would also like my buddy Carly Aquilino. She is as straight as I am gay, so we are very different, but it’s the same feel-good type vibe.

When you started performing standup comedy, you were living in Boston and enrolled in comedy classes there. Based on your experiences, would you encourage new standup comedians to develop their style and material in a smaller market first, before moving to, say, New York City or Los Angeles?

Yes! One hundred percent. But here’s the kicker with that: Besides doing comedy, there is also your life. And moving is insanely hard. While you are developing, you might start dating, get more responsibilities at your day job, all that stuff. Then you start to get opportunities in the smaller market and it feels good because it’s a tad bit of a break. So moving becomes harder and harder. For that reason, I recommend starting in a smaller market, but with caution. Make as many trips out to NYC or LA as you can to watch other performers and see what they’re up to. Try to start a show to network with other comics coming through the area, or make viral videos and get famous that way. Just don’t get stuck there and lose perspective of your market or the grand scheme of things.



Standups famously have to contend with hecklers and adversity during their careers, especially when they’re first starting out. During the early days of your career in comedy, you had to deal with a particularly nasty heckler during a competition, but you used that experience as fuel to go back and win that same comedy contest the following year. In that sense, do you think adversity can be a good thing?

You need adversity, especially in something like standup, because you need to have been through worse and pulled through to know that you can get through this next thing. And while trying to “make it” is so isolating and hard, you have to be okay with being the other. You have to be okay with no one understanding what you are trying to do, especially when you’re starting out. For instance, I think about this one class on entrepreneurship I took in college. This entrepreneur came in and said that for years everyone thought she was nuts. She was working all the time, even sleeping under her desk. I thought she would say, “This went on for four or five years,” but no. She said, “Around the 12-year mark…” And that stuck with me. It’s a long journey. Nothing is everything, but everything is something, and the build takes time. For this woman, it was year 13 when her company finally popped off and suddenly her world changed — but knowing that’s the time frame, with all the risk and uncertainty, I can’t imagine how someone who hasn’t experienced adversity can then throw themselves into that voluntarily. And, yes, throwing oneself into it is absolutely a privilege, but it sure isn’t a sign of good mental health. (Laughs.)

How do you balance 18 to 25 shows a week with podcasts, TV shows and generating new material? How do you cope as an artist? And do you have any advice on self-management for other up-and-coming comics?

I don’t balance everything very well. I’m overwhelmed and irritable a lot, and I am always the most critical of my standup. Sometimes I’ll exercise, but not really. If we were on a date right now, I would say, “Oh, I exercise, spend time with friends and make sure to have other interests.” That would be a lie. And straight up: The downside of all that, and the travel, can be super problematic on my stress levels. So how I cope is…I just keep trying to go forward and hope I figure out how to cope down the road.

As for advice, you have to understand that you will never make it. And then, with that understanding, work to prove me wrong. Also, figure out what “making it” is to you. If you can be happy just being in the community and bopping around, sure, that’s a possibility. But “making it, making it,” where you are a draw and have a sitcom, etc. — that will never happen. It’s impossible! Now prove me wrong. Be smart, work hard, and just know that it’s impossible and you are going up against incredible odds — never forget that. People get so focused on getting into this club or that festival (I know this because I do it too), but don’t lose sight of the bigger picture. Throw yourself in there, and if you don’t get it, don’t wait for it. Keep getting better and keep it moving. Also you should be scared out of your mind because it probably won’t work out. Am I projecting?



Be sure to follow Emma on FacebookInstagram and YouTube. You can also check her schedule for live performances near you. And don’t forget to tune in to The Check Spot on Sirius XM Channel 99 on Tuesdays. Why? “Because I get to showcase other people! I love doing that! I love seeing someone who is funny but doesn’t have an album out yet or just put an album out, and getting them on radio. It’s fun, feels good, and the karma always comes back around!”