Laugh track

Steven Castillo lands ‘SNL’ gig—by way of The Loony Bin and Second City

When Steven Castillo started performing comedy eight years ago, he had big dreams. After stints in Tulsa, Chicago, and Los Angeles, Steven is experiencing the realization of those dreams—he recently started writing for “Saturday Night Live.” Though he spends fewer nights performing and more nights in his office, he’s loving it.

Andrew Deacon: It’s interesting watching the local reaction to your new job. How’s it feel so far?

Steven Castillo: It’s crazy. I’ve been living in this bubble for a while. When I got it, it didn’t seem like a big deal, and then all these people from Bishop Kelly were messaging me. I knew all the people from the Loony Bin would reach out, but I wasn’t expecting the response I got. It’s overwhelming—in a good way.

Deacon: Was working on “SNL” part of a trajectory you always saw for yourself?

Castillo: I think so. The reason I moved to Chicago was to work on “SNL.” I was introduced to Second City through a workshop at TU. All the people that went to Second City eventually went to “SNL.” The ultimate thing was to wind up there. Once I was in Chicago, I found out just how hard it was to be on [“SNL”]. So many people audition, so I didn’t think about it much. But early on, it was definitely something I wanted.

Deacon: How does it feel to write for “SNL” during such a politically -charged time?

Castillo: One thing I noticed the first week there is that I’m surrounded by the smartest people I’ve ever been around. They’re so politically savvy and so up-to-date. Colin Jost is a modern Renaissance man—the quickest, smartest, most well-put-together person. There’s a lot of people like that at “SNL,” and it’s been really inspiring. It’s really helped shape me. I’m reading so many articles during even my off weeks. I’m definitely more up-to-date. It’s amazing to be in a room full of people who are incredibly smart, witty, and in touch with our political environment.

Deacon: I remember watching you perform stand-up at The Loony Bin in 2013. You were much younger than most of the comics. What inspired you to get into stand-up at such a young age?

Castillo: I never saw myself as a comedian. I wanted to go to film school and become a director. One of my friends from high school was doing an open mic at The Loony Bin. I decided to film a documentary about stand-up open mics. They had a workshop Wednesdays where you would go onstage and practice. You would perform for Corey Douglas, Dan Fritschie, and Hilton Price. I thought that was fascinating, practicing your jokes before you got in front of an audience. There was something about seeing all those guys go up. I didn’t think I could write a joke, but I did think I could say something funny. I [thought] I could deliver something funny.

Then I did my first open mic there and it might have been the best show I’ve ever done. I’ve never felt such a high. It was the first time I felt cool and good at something. Then it became an addiction. The way stand-up is, I’d go back to The Loony Bin the next week, do the exact same set and bomb. It’s important to say how much I love those guys I started with. They were my first clique. In high school I didn’t really associate with anybody. I wasn’t necessarily a nerd or cool, but with those guys was the first time I felt included. That was another reason I kept at it.

Deacon: How did working in Chicago shape your comedy writing and performance?

Castillo: While living in Tulsa, I did a lot of improv with the group Crayons. A big reason I moved to Chicago was the improv scene at Second City. When I was doing stand-up in Tulsa, a lot of my comedy was geared towards The Loony Bin. It wasn’t necessarily material I was proud of, but I knew it would get a laugh there. When I did that same material in Chicago, they saw right through me. I was going up night after night, bombing hard. That’s when I bought a Bluetooth speaker that I use in my act now. I would have it there so I could add a laugh track, because no one was laughing. That’s when I started the act I’m doing now. My routine has become incorporating these dumb, silly bits.

Deacon: You’ve done conceptual shows like “Steezus,” where you take on the persona of Kanye West. Do you have plans to do more of these types of performances now that you’re in New York?

Castillo: Yeah. I’m planning on creating a new solo show this year with a similar theme. One of the nice things about doing this job is that you have off-weeks, where I perform as much as I can.