Jay Duplass knows a thing or two about Hollywood’s A-list.

The acclaimed writer, director and actor has worked with John C. Reilly, Catherine Keener, Jason Segel and countless other stars. Now, in an unexpected career twist, Duplass is betting on a relative unknown from Towson to carry his next movie, “The Baltimorons.”

Risky? Certainly. But Duplass is confident Michael Strassner is “our next comedy star on the rise.”

“He has it all,” Duplass said in an interview. “He’s funny as hell. He has no emotional blocks. … I think he’s unstoppable.”

Early returns suggest Duplass’ wager could cash out. “The Baltimorons,” the first film he’s directed in 14 years, has emerged as an indie critical darling, picking up festival awards and enthusiastic reviews on the way to its Maryland premiere and national theatrical release next week.

Strassner, who co-wrote the romantic comedy with Duplass, is processing the praise and attention over a story that, despite its heart and big laughs, is inspired by the darkest moment in his life.

“I’m just so grateful that I’m here,” the 36-year-old said.

‘He was a character’

Ask James Katchko about his former student “Strass” and a wide smile immediately comes across his face. The chairman of Loyola Blakefield’s performing arts department recalls a popular and kind teen with a “big personality.”

“I would not say he was a troublemaker,” Katchko said. “He was a character.”

Strassner quickly realized how much he loved making others laugh. He remembers throwing on his sister’s dress after seeing “Mrs. Doubtfire” and studying Chris Farley’s physical comedy in “Tommy Boy.”

Though Baltimore “will always be home” to the lifelong Orioles and Ravens fan, Strassner moved to Los Angeles to pursue comedy after graduating from the University of Maryland, College Park, in 2011. He chose California over New York as a form of commitment.

“If I go to L.A., I’m only coming back twice a year and I’m just focusing on this career,” said Strassner, who has guest credits on “Parks and Recreation,” “Modern Family” and other TV series. “And that’s kind of what I did.”

In Los Angeles, he also embarked on a major lifestyle change: sobriety. Strassner said, when mental health concerns flared up, he’d “keep drinking to push it all down.” Alcohol went hand in hand with the comedy lifestyle, too.

But, over seven years ago, Strassner, at his bleakest, tried to hang himself. The belt broke. The next day, he gave up booze and asked for help. “It’s the best thing that ever happened to me,” Strassner said.

A new concern, however, soon filled the void. Could he still be funny?

‘I’m so proud to be from there’

Set and filmed completely in Baltimore, “The Baltimorons” doesn’t shy from familiar movie charms.

Strassner’s Cliff, an improv comic who has lost his way, needs an emergency dentist. He meets the older Didi (Liz Larsen), forming an odd couple with a will they-won’t they dynamic that reveals these two characters need each other more than they knew. It all takes place during Christmastime, adding another layer of rom-com irresistibility.

“The Baltimorons,” named after its protagonist’s sketch group, tackles Cliff’s concerns over sobriety and comedy head on — even opening the story with his suicide attempt. But there’s little doubt over Strassner’s chops. Cliff is an everyman, but few civilians possess the mix of warmth, wit and comedic timing Strassner emanates in the film.

The hardest part, Larsen said, was to avoid being won over by Strassner’s character too quickly. The veteran actress described Strassner as “irresistible, adorable and soulful.”

“I kept saying, ‘Jay, is it too fast?’” Larsen said. “I had to temper because I just loved him so much.”

While the duo’s chemistry drives the narrative, the true love story is arguably the film’s unabashed affection for its setting. “The Baltimorons” features gorgeous, wide-angle shots of a city whose beauty is too often ignored or denied by outsiders.

Many city residents will be delighted by the details, from the obvious — Hampden’s Miracle on 34th Street, the Guilford Avenue Bridge, rowhome interiors — to the more granular. In one scene, we learn Didi’s ex-husband, donning purple camo cargo pants straight out of a Ravens tailgate, wanted his wedding song to be “Orioles Magic.”

Most arresting are the shots of the Key Bridge, filmed just months before tragedy struck. The end credits include a tribute to the six maintenance crew workers who died in the bridge’s collapse in March 2024.

“It’s just such a surreal thing to see it, and I feel sad but also really proud that we were able to shoot it in a beautiful light,” Duplass said.

“The Baltimorons” was shot in weeks, not months, on a “shockingly low” budget, Duplass said, with a production crew of roughly 15 people all from the city. In true Smalltimore fashion, they leaned on friends and family for help.

“My great-grandmother’s house is where Cliff cracks his tooth,” producer David Bonnett said.

“The Wire” was celebrated for its realism. Strassner, who called the HBO series “incredible,” hopes “The Baltimorons” will be, too.

“Every time I come home, it’s around the holidays, and the love and joy that’s felt in that city is beautiful. [Duplass and I] wanted to show the city in a positive light because it is a positive place. I’m so proud to be from there,” he said.

‘It is an audience award magnet’

Since its March premiere, “The Baltimorons” has had the start independent films dream of — winning the prestigious SXSW Audience Award at the Austin, Texas, festival before IFC Films and Sapan Studio purchased its U.S. and Canadian rights. International rights were also just secured.

“‘The Baltimorons’ Is the Year’s Most Charming Romantic Comedy” declared the Daily Beast, echoing other glowing reviews that resulted in a 97% fresh score on Rotten Tomatoes as of this article’s publication.

Duplass, who shares directing credits with his brother, Mark, on films including “The Puffy Chair” and “Cyrus,” has been shocked by the reception.

“I’ve made much, much bigger, more expensive, more star-studded movies, but no movies have won audience awards in the way that this film has. It is an audience award magnet,” he said. “What I’m hearing … is ‘This is actually the movie that I want to see on Saturday night with my partner.’”

And to think this partnership began years ago, when Duplass stumbled upon Strassner’s Instagram account and gave the up-and-coming improv actor a follow.

“He’s the best director in the world,” Strassner said. “I think there’s nobody better than him.”

Next week, Strassner is crossing two more items off the bucket list; he will throw the first pitch for Orioles-Pirates on Wednesday before rushing over to the Senator Theatre for the film’s sold-out Maryland premiere, where he and Larsen will hold an audience Q&A. (If you missed out on tickets, “The Baltimorons” opens at the Charles Theatre the following day.)

Strassner’s schedule is getting busier. Last month he starred in a new independent movie called “Tuesdays New York,” and now he’s shooting “The Musical” in Los Angeles with Tony Award winner Will Brill, Rob Lowe and Gillian Jacobs. He also has a wedding to plan — he got engaged in May to actress Jessie Cohen, who makes a cameo in “The Baltimorons.”

Strassner, though, is looking forward to savoring a taste of home next week. Some crab cakes and a trip to SnoAsis for snowballs are part of his usual routine. If his star is taking off, then Strassner wants to cherish the journey, including the trips back to Baltimore that keep him grounded.

“I’m so grateful that I get to do this for a living right now,” he said. “And I just hope it keeps going.”