There are some days that start off bland and then spin strangely and sensationally to change your life forever — for the better.

Jay Duplass’ The Baltimorons is about such an extraordinary day. Co-writing this comedy with leading man Michael Strassner, director Duplass crafts a journey that is an absolute side-tickling and soul-enriching delight — and it all begins with a broken tooth. 

After a robust slate of productions with his brother Mark Duplass — recently including Penelope and The Creep Tapes — this is Jay’s first solo venture. Yet he stays true to the Duplass’ mumblecore roots. The Baltimorons is proudly a low-budget, character-driven comedy starring actors who look less like movie stars and more like the folks you see at any given grocery store. However, the humor blooms more broadly than the mumblecore of their Puffy Chair and Baghead origins, with leads Michael Strassner and Liz Larsen, who are absolutely enchanting as an unlikely but undeniably dynamic duo brought together by happenstance and held together by good fun. Together, they craft a chemistry that steadily bubbles into an eruption of shenanigans and joy. 

The Baltimorons is a classic comedy out of the gate. 

Duplass has found a top-notch collaborator in Strassner, whose comedic timing and scruffy charisma are absolutely extraordinary as outgoing Baltimore local Cliff Cashen. A thirtysomething former improv comedian — who was once on the brink of breaking through on a certain New York sketch show — Cliff is six months sober on Christmas Eve, with his fiancée (Olivia Luccardi) urging him to attend a family dinner and his old troupe begging him to come back to the stage for a show that night. Both possibilities for festive fun are threatened when Cliff accidentally breaks a tooth, forcing him to embark upon a side quest for a dentist who’ll see to his emergency on a holiday. 

Enter Dr. Didi Dahl (Liz Larsen), a sixtysomething, no-nonsense divorcee with a sharp sensibility and a tender heart. Doped up on laughing gas, an unguarded Cliff can’t help but remark on how pretty Didi is and how nice she smells. Dr. Dahl has little patience for this teddy bear of a younger man — at least until his car gets towed. Then her cool exterior cracks into a warm grin as she plays Good Samaritan with some well-meaning mischief. Didi’s plans for the holiday have been ruined by her selfish ex-husband, but following Cliff’s lead takes her down an unexpected path of discovery, low-level crimes, juicy payback, and second chances. 

At first glance, these characters seem to have nothing in common. He’s a sweet and funny but lost millennial, who’s left his comedy dreams behind to become — maybe — a mortgage broker. She’s a boomer, hardened by a soured marriage and a demanding career, but can’t deny the charms of this beguiling goofball — even if she says he’s a “real Eddie Haskell … full of shit!” There’s a tantalizing chemistry in the way they banter, not letting each other get away with anything. And as tempted as I am to give an example by laying out a punchline about holiday weight, it’s just too good in context to spoil. Let’s just say it’s thrilling to watch two strangers truly see each other, and mutually delight in that discovery.

Michael Strassner is a comedy star in the making. 

There’s a jolly gameness to Strassner’s comedic persona that is instantly charming, making even an early joke about a failed suicide attempt joltingly funny in his hands. Strassner has a vaguely Bill Murray-ish quality about his humor, whether in moments of buffoonery or taboo subject matter. Yet he doesn’t carry the smug self-assurance of ’80s Murray, instead brandishing a cherry-cheeked vulnerability that makes The Baltimorons feel deeply of this moment. Cliff is a modern man, grappling with thwarted dreams, personal failures, and a confounding path to the future. But he does so with an open heart and a smart mouth that makes for brightly hilarious scenes, whether Cliff’s doing schtick with a thick Baltimore accent or trying to impress some rude Ravens fans. 

Liz Larsen is his perfect scene partner. There are shades of Edie Falco’s Carmela Soprano in her “don’t mess with me” energy, signaling that Didi has been burned before and isn’t looking to get hurt again. But when Larsen smiles, you can see the hopeless romantic who still yearns in Didi’s heart. She becomes radiant, whether pressing Cliff to take a big risk or barking orders from a crabbing boat. Their adventure takes them all over Baltimore, from quiet residential streets to sketchy parking lots, bustling holiday parties, and a spot offering a serene view of the water. Along the way, we feel lucky to be along for the ride, nestled in by Duplass’ subtle but strong world-building of his characters’ Baltimore.

Essentially, The Baltimorons is a celebration of those moments when — despite all the reasons to shield ourselves from a cruel world — we open up to a new friend. It’s about the magic in being vulnerable, not out of naiveté but out of hope.

The screenplay by Duplass and Strassner neatly captures the excitement and tension of such a social gamble, balancing moments of heartache and comic elation. Strassner and Larsen bring this theme to vivid life with portrayals that play similarly to Duplass’ odd-couple comedies like Somebody Somewhere and Biosphere. Which is all to say, The Baltimorons is an absolute gem. Deftly modern and smartly self-aware, it’s not only one of the best things I saw out of SXSW, but assuredly one of the best films of 2025. 

The Baltimorons was reviewed out of its World Premiere at the 2025 SXSW film and TV conference.