In ‘The Baltimorons,’ Michael Strassner Gives Charm City the Main Character Energy it Deserves

In 2021, almost a decade after moving from Towson to California to pursue a career in acting, Michael Strassner was steadily working, but not quite crushing it. He joined The Groundlings, the famous Los Angeles improv troupe, and had some success there. He came this close to being on Saturday Night Live—callbacks and everything. He got small parts in major TV sitcoms (he played Nick Offerman’s brother in Parks and Recreation). But he hadn’t really had his big break.

That is, until the writer-director-actor Jay Duplass (one half of the acclaimed Duplass brothers) followed him on Instagram. Strassner seized the day and sent him a DM. The two met, got along famously, and decided to make a film together.

The result is The Baltimorons, an underdog romcom about the relationship between Cliff (Strassner), a newly sober 30-something improv actor loosely based on Strassner, and Didi (Liz Larsen), a middle-aged dentist. (Read my full review, here.)

The film, which is entirely set in Baltimore, was a huge sensation at SXSW and will soon be playing in the town that inspired it. The sold-out Maryland premiere, featuring a Q&A with Strassner and Larsen, will take place at The Senator on Sept. 10, with more showtimes at The Charles and other local theaters to follow.

Ahead of the local premiere, we caught up with Strassner to discuss his love of comedy, how the film came to be, and giving Baltimore the star treatment it deserves.

Tell me about your background. Where did you go to school—which, since you’re from Baltimore, you know means high school.
I know, indeed. I’ll do the whole pipeline. I went to Hunt’s [Church] originally, then Riderwood, then Immaculate Heart of Mary for middle school, and Loyola Blakefield for high school.

How did you get into performance?
I kinda got my first itch for theater at Immaculate Heart. I got to be Snoopy in You’re a Good Man, Charlie Brown and Hugo in Bye Bye Birdie, even though I wanted to play Conrad. And then off to Loyola—I did a little bit of sports there, but I just always loved doing theater. I was part of the Blakefield Players. I went to East Carolina University for a year and then I transferred to University of Maryland. I was originally a business major and then I realized, this is not what I want to do. I want to be an actor. And so I changed to theater. And by February of 2012 I was out to L.A.

I had assumed your background was improv and comedy. But your background was acting.
Right after college, I went to L.A., and that’s when I started doing improv and sketch comedy. Before that it was all theater and plays. If I’d done my research a little better, I would’ve realized that my heroes came from the Chicago scene: Bill Murray, Chris Farley, Mike Myers, John Belushi. They were all Second City people. But I was in L.A. and I was like, well, who else do I love? Will Ferrell and Kristen Wiig and Phil Hartman. Well, I guess I’ll do The Groundlings.

While you were at The Groundlings, you got an opportunity to audition for SNL.
A rite of passage, truly. It was 2016 or 2017 and I tested with my friend, Heidi Gardner, who ended up getting it, of course. We did a showcase in L.A., then they brought three of us out to New York and then back to L.A., and then we came back for our final test in New York. It was very surreal. Lorne Michaels was there eating popcorn. They say it’s a rough room, but I did get some laughs, so I felt good about that. And I was like, “Okay, this is it!” And then it wasn’t.

Is there a feeling not getting SNL might’ve been a blessing in disguise?
One hundred percent. I was not sober at the time and I feel like if had gone there while I was still in active addiction, I never would have survived. I would’ve ended up like one of my heroes.

You started getting some small roles on major sitcoms. And then what?
In 2021, two things happened: I saw that Jay Duplass followed me on Instagram, and I had a short film that I wrote and I was hoping to find an actress for it. And I thought, “I’ve heard this guy helps out people. Let me send him my script in a DM.” …Six months later Jay replied. He wrote, “I’m super old. I don’t know how Instagram works, but send me your script.” And then he said, “Come over to my house.” And I was like, “I’m a stranger on the internet! You’re a celebrity. Why are you giving me your address!” [Laughs] And we had lunch.

You later made the short and sent him a copy, which he liked.
Yeah, he took time out of his day. And this is the kind of stuff that doesn’t happen in L.A. At least it doesn’t happen for me. It’s really a testament to Jay and Mark at Duplass [Brothers Productions]. They really want to help the next batch of independent filmmakers.

Over time, you told Jay your story, including your sobriety journey, and one day he said, “Let’s make a movie.”
Yeah, he said, “Hey man, I really want to turn your life into a movie. You want to do it?” And I was like, “Yes, please.”

You guys wrote The Baltimorons together. Was the plan always for you to play Cliff?
When we were writing it, I asked Jay, am I gonna act in it? And he was like, yeah man, you’re going to be the star.

This is a cliché, but it really did feel like Baltimore was a character in the movie. Was that intentional?
Yeah. I mean, we really wanted to make it a true love letter to Baltimore. I just love this city so much. I tried to have these authentic Baltimore things throughout. Natty Boh was super nice that they gave permission to use their stuff, and Berger Cookies. And the city is filled with so many people who are willing to help. I had so many extras who were my family and friends. People just took time out to help and it was the most beautiful thing. Places like Rocket to Venus and Dylan’s [Oyster Cellar]. We were like, “Can we use these locations?” And they were like, “Of course!”

I feel like Baltimore doesn’t always get this treatment. It’s usually Chicago and Boston and New York that are mythologized like this.
I grew up watching John Waters. I grew up watching Barry Levinson. I think what David Simon has done is great, but it never really shows the city in the best light. I feel like this city has so much more beauty and that it’s time we show it again. And we have our, like, Woody Allen Manhattan shot of the Key Bridge, which is my favorite shot, truly the most beautiful shot of the movie. We got that two months before it fell. It’s such an honor to have that in there. And 34th Street [also featured in the film] is a place that I grew up loving as a kid. I’m a Christmas nut, so the fact that we were able to, just like, shoot on 34th Street was like the coolest thing in the world.

So, speaking of John, has he seen the film yet?
He has. He came to the Provincetown screening and that was really cool. He sat in the back row, and he even stayed for the Q&A and was super sweet and kind. And he asked a question. He said, “How did you get to shoot on 34th Street? I’ve wanted to shoot there for forever!”

You have amazing chemistry with your co-star Liz Larsen.
It was immediate. We just kind of fell in love with each other in a platonic way, which was a blessing because if she and I aren’t vibing the movie [fails].

Tell me about the SXSW screenings. Your whole family and lots of friends, many of whom were in the movie, came.
My dad and step mom came to one screening and my dad is just going throughout the whole entire movie saying, “Oh, there’s Alison, there’s Lauren, there’s Dell, there’s Marty.” And I’m like, Dad, it’s not a private screening. You can’t just be saying everybody’s name you’re seeing in the movie!

Let’s talk about the title, Baltimorons. That’s kind of an inside joke for locals. Are you concerned some might take it the wrong way?Well, that’s the name of Cliff’s sketch group [in the film]. But if I didn’t come from Baltimore, I wouldn’t be caught dead naming the film that.

Coming home to shoot this film must’ve been quite a heady experience for you.
I mean, the best thing that’s ever happened to me is my sobriety. But number two is shooting this movie in Baltimore. You know, the fact that I got to come home to make my first movie as a lead, it was truly an honor. We would leave the set sometimes at 5 a.m. and I just remember driving past M&T Bank Stadium as the sun was coming up, and I’m like, this is my dream. It doesn’t get better than this.

Read my full review of The Baltimorons, here.