Leap of Faith: Why comedian Deshawn Mason moved to Amsterdam without ever having visited

Deshawn Mason would most likely have joined the U.S. Air Force were it not for a serendipitous encounter at his retail gig, where he sold pants to a comedian one afternoon. The more established comic helped Mason jump on his first stage for an open mic night in Charleston, South Carolina, and Mason was hooked on performing.

Now 33 years old, the improvisor, stand-up, and magician had made a pact with his mother to still join the service unless he found his calling by the age of 22. Luckily, that calling found him, and his sharp wit and talent helped him develop his craft and career in Georgia, before getting a chance to tackle the legendary comedy scene in Chicago.

But it was another leap of faith, moving to Amsterdam without ever having visited, that truly cemented his career. He got a shot at a coveted spot on the mainstage at Boom Chicago this past Spring, and he has not looked back. Mason sat down with the Dam Yankee Podcast, in partnership with NL Times, to reflect on his career.

Dam Yankee: Did you always have a sense that you would be a performer?

Deshawn Mason: A friend of mine in high school, he kept saying to me, he was like, "Deshawn, you could be a standup comedian. You're really funny." And I was also not great at school. And I do remember one specific day he was like, "Deshawn, you're bad at school. You do this stuff. You’re kind of living like every comedian's life up to this point." And then I started writing down jokes. I would say things in conversation.

And then I kept this sheet of paper in my wallet that had a set list. And I updated it over the course of like, I want to say, like two years or something like that. And then eventually a guy wandered into the Hollister that I was working at, this clothing store. And he was like, “Hey, I'm a comedian and I need pants.” I got a show this weekend. And I was like, “Hey, that's crazy.” And I asked him if there were any open mics. And there was one that night.

DY: Were your parents supportive of your career path?

DM: They've always been pretty supportive. When I first started doing comedy, I was also thinking about joining the military. I was going to join the Air Force. And I'd gotten through about to go to basic training.

So my mom was very excited about that. And when it came time to sign the papers, I kind of backed off. And I was like, I don't know. I think I kind of want to do comedy. And my mom, to give her credit, was okay with it.

But she kind of came up with a deal that by the time I was 22, if I didn't know what I was doing with my life, then I would go and join the military. So then, yeah, I was doing comedy. I started going to college a little bit, just like a technical school, nothing too serious. And then like I remember a week before my 22nd birthday, I probably was walking around like a zombie and trying to avoid her.

And she just caught me in the living room and was like, “Hey, I don't know if doing comedy is a good idea, but if you think it is, then it's okay if you just want to try to focus on that.” And so then I did. Then I just started doing lots and lots of it and the standup was going well and I was traveling around and having nice little successes and different things like that.

DY: It sounds like a huge change in such a short period of time.

DM: I think I will also say my stand up ability at the time– I think like in 2019, since I was doing a lot of festivals and stuff, I did feel like a very strong performer and I felt safe in that. Like when I was doing stand up, I remember the first time I ever did it, it felt like it was the first time my brain worked right. Part of the reason I love the stage now is like it's the only time in my life that I feel like I'm not supposed to be anywhere else or I don't need to be anywhere else.

So I feel like in improv, I found out that I could let myself feel like that all the time. And the process for me is just like continuing to remind myself of that and continuing to build those skills and tools so that way I know that everything's okay. Because everything is usually okay.

Of course, that doesn't mean that bad things can't happen or this or that or setbacks. But rather than view is as a setback, it’s like something that I can come back from

Now they're just kind of an interesting part of the story that is continuing to unfold. I can't wait to see how I get to turn this like raw material into like golden thread.

Listen to this entire episode of Dam Yankee wherever you get your podcasts, or watch the full videos on YouTube. Deshawn Mason dives deep into his origin story as a magician, exploring the stage as a safe space, and his nuanced view on the “laughs per minute” formula.

You can see him in action at Boom Chicago every Wednesday through Sunday. Keep up with all him on Instagram as well at @Mason_san.