Matt Walsh's latest role in ‘The Unexpecteds’ is his most unpredictable yet

Chicago comedy guru Matt Walsh has played a few unexpected roles in his life: a college professor on “The Conners,” a detective on “Brooklyn Nine-Nine,” a doctor in “The Hangover” and, of course, the important director of communications for Selina Meyer on the TV series “Veep.”

But his role in the new movie “The Unexpecteds” may be his most unpredictable yet.

In the modern caper, which screens at two Chicago premieres this weekend, Walsh plays main character Gary, an everyday father, husband and corporate schlub looking for a break in life. Along with a handful of well-meaning friends, all get sucked into a social media “get rich quick” crypto scam. And after being swindled out of their life savings, they enact a plan to get their due.

While the indie film tackles the plot with humor, some underlying themes elevate it from a one-dimensional comedy. For one, it’s a tale of the underdog.

“My grandfather was taken by a lot of [scammers]. They took a lot of money from him before he died,” writer/director Alejandro Montoya Marín said during a recent Zoom call, where he was joined by Walsh from the actor’s Hollywood home.

“I see a lot of people get away with stuff, while others try to do the right thing and not succeed,” Montoya Marín said. “This is about underdogs getting theirs. Even though they're all kind of klutz motivated by hope and anger, their heart is in the right place.”

A strong father-son dynamic runs through several of the main characters’ story lines, from Gary’s down-on-his-luck friend Carl (a struggling actor played by Francisco Ramos) and his mysterious agent father Felipe (Alejandro De Hoyos). By the end of the film, Montoya Marín has a tribute before the credits roll: “para mi papa” (for my father).

The arc drew Walsh to the film, as did his previous relationship with Montoya Marín (the two previously worked together 2023’s “Flamin’ Hot”).

“I think father-son relationships are fraught with masculinity-slash-success, and there's a sense to prove that you're as good as the man you came from in a way,” said Walsh, who has two sons. “I think there's a lot of that in this story about men who have failed and are trying to prove that they are good.”

Walsh said the role brought up memories of his late father and how concerned his father was after the budding actor, a graduate of Northern Illinois University who had cut his teeth in Chicago’s improv clubs, uprooted to New York.

“I was, like, 31, I moved there with [sketch comedy troupe] Upright Citizens Brigade. I lived in an apartment with four other guys. I had sold my van and that money was going to make or break me for six months,” Walsh recalled. “My parents came to my apartment in Hell's Kitchen, and there was an outlet with like 24 plugs plugged into it. My father was in the construction and safety world and was like, ‘This is going to cause a fire. What are you living like?’”

Last November, “The Unexpecteds” won Best Comedy at Kevin Smith’s Smodcastle Film Festival, and the “Clerks”/”Dogma” indie kingpin has given the film his personal blessing by joining on as an executive producer.

“I've been a fan of his since ‘Clerks,’ since I was 10,” said Montoya Marín. “I wasn't supposed to see those movies, but that string of ‘90s greats like Tarantino, Soderbergh, Rodriguez, Bigelow, all of them I've been a fan of.” In fact, Montoya Marín worked closely with Robert Rodriguez in the documentary series "Rebel Without A Crew.”

“I think there has been a real disruption in the status quo of entertainment and the things that are getting made,” Walsh said. “I also think outsider art is being welcomed more than ever.”

To his point, “The Unexpecteds” has been offered screenings by two Chicago independent institutions that will offer screenings, red carpets and Q&As with Walsh, Montoya Marín, De Hoyos and actress Chelsea Rendon (Pati) this weekend. CHIRP Radio will host an event at the Davis Theater in Lincoln Square on Sunday and the Latina Expo will host an event at Malcolm X College on Saturday. (The latter organization is representative of not only Montoya Marín’s heritage but also of the predominantly Latino cast in the film.)

“As someone that comes from Laredo, Texas, who was raised in Mexico, studied in Canada, lived in Albuquerque, and now lives in L.A., I'm a pozole of culture,” Montoya Marín said. “What I wanted to do was to make a movie that will hopefully be enjoyed by anyone, and I think that reflects in the friendships because they're so different … but what they had in common was them wanting to do something extra, to live a better life.”

As the tag team heads to Chicago this weekend, each has another agenda. For Montoya Marín it will be continuing to scout locations for his next Chicago-filmed project, an adaption of the music time travel book “90 Days in the ‘90s,” written by local talent Andy Frye (who leads the Q&A Sunday). For Walsh, he plans to see his mom and siblings in suburban LaGrange, maybe take in a Cubs game (“I’m on the bandwagon,” noted the South Sider) and hit up some vintage stores.

“I enjoy a good used bookstore in Chicago or a good vintage store even like Salvation Army or Brown Elephant,” he said. “I like getting in there because there's some great stuff to be found. And it's good for the environment.”

But ultimately, the goal for their trip is to find an audience for “The Unexpecteds.”

“I think if you can win over a Chicago audience with comedy,” Walsh said, “you can do so anywhere.”

After this weekend’s events, “The Unexpecteds” gets its global release Oct. 14.