The Baltimorons/Duplass Brothers Productions
3 stars (out of 4)
Director: Jay Duplass
Starring: Michael Strassner, Liz Larsen, and Olivia Luccardi
Language: English
Available: Limited theatrical release September 5
Here’s the challenge: Make a funny, romantic feature with a backdrop of failed suicide attempts, divorce, romantic breakups, outworn ambitions, DUI arrests, and the gritty side of a big city. Not exactly Sleepless in Seattle.
And yet The Baltimorons fires on all eight cylinders to become what may be the happiest holiday film of 2025, a date-night movie for any month, and one of the most charming pictures I’ve seen this year.
Christmas Eve has arrived. In bedraggled Baltimore—think graffitied fences, train overpasses, the sounds of the city—former comedian Cliff Cashen (Michael Strassner), newly sober and engaged to Brittany (Olivia Luccardi), accidentally knocks out a tooth (the “back right 30,” in dental parlance) and goes in search of a dentist still open on the holiday afternoon.
Gruff, middle-aged, Gen-X dentist Didi (Liz Larsen), whose Christmas Eve plans have been ruined by her former husband, agrees to see him. Her daughter and grandchild won’t be coming to her house for Christmas Eve dinner anyway, because they’ll be attending the wedding reception of her ex, who had the gall to get remarried that very morning.
It turns out that millennial Cliff, a big man but gentle-hearted, is deadly afraid of needles. So Dr. Didi, in one of the film’s most hilarious scenes, turns on the nitrous oxide. (“A super pretty hero,” Cliff says from deep inside ga-ga land. “Super pretty woman hero.”)
In his efforts to overcome his drinking, Cliff has joined AA and stopped performing stand-up, convinced that alcohol and comedy are intertwined. At one point, as they enter a comedy club, Cliff tells a famished Didi, “They’re not gonna have soft shells at the improv show. Probably just jelly beans and vodka.” Which sounds like it might have been his former daily diet.
The comedian’s frequent and often inept joke lines, even when inappropriate, can’t be helped. They gurgle from his mouth like a poorly maintained elementary-school water fountain—they spurt out when least expected.
As Cliff and Didi head out into the dark holiday night of a Baltimore winter, awkward, slightly felonious incidents crop up, eventually leading to an arrest.
But as their relationship grows, and a hint of romance fills the air, so too does beautiful Baltimore begin to shine thanks to Jon Bregel, director of photography. That’s especially true in the scenes shot in the hipster neighborhood of Hampden, in the brick-lined streets of Fells Point, and in the nighttime water shots of the city’s famed Inner Harbor with the lights of the skyscrapers flashing on the waters of the Patapsco River.
The screenplay, written by director Jay Duplass and lead actor Michael Strassner, strikes an authentic note. Despite Cliff’s comedic tendencies, his sometimes cringey attempts at humor are never over the top. The Christmas references are low-key and sometimes obscure (“Your family lives on 34th Street?!” Cliff asks at one point). The language and the situations are family-friendly, but I doubt that kids under 14 would appreciate this movie.
Didi and Cliff are emotionally appealing in distinct ways: she, buttoned-up, terse, a workaholic trying to overcome her ex-husband’s emotional abandonment; he, a failed comic, a loser at love, alcoholic, an unsuccessful suicide, hapless, and often befuddled in a cuddly sort of way. They are two people at the end of a tender, fast-fraying, psychological rope—in Cliff’s case, literally. Together, they make an unlikely but ultimately lovable couple that you can’t help but root for.
Throughout the evening, their deeply held fears bubble to the surface. Didi faces the prospect of growing old, alone. Cliff, barely clinging to his newfound sobriety, comes to grips with the end of his comedy career and a bleak future in, of all things, mortgage loans. Maybe.
When Cliff makes an unexpected return to the comedy stage, the romance between dentist and patient grows from a wispy possibility to something you can sink your teeth into.
Something else you can bite on: the jazzy holiday soundtrack by Jordan Seigel. Clearly, Seigel has been visited by the ghost of Vince Guaraldi, who played the music in the Peanuts TV specials, including A Charlie Brown Christmas. It’s an endearing sonic seasoning, perfectly in sync with the story. I’m adding the soundtrack to my own Christmas wish list.
The film’s pacing is precise. As easygoing as it is, not a moment is wasted in this 101-minute film. The writing seems as if Duplass and Strassner know these characters in real life, so authentic is the dialogue. And Cliff’s frequent funny asides kept a smile on my face, even when I wasn’t laughing out loud.
But Cliff and Didi must make some serious decisions.
Will Cliff return to his fiancée or start anew with a 40-something dentist that he met less than eight hours earlier? Can he summon the courage, in his newly sober life, to return to the comedy that was once fueled by booze? Can Didi reclaim happiness and satisfaction, even though her husband dumped her?
In the end, it doesn’t matter whether we get those final answers. Life isn’t that tidy.But by the end of The Baltimorons, we have a pretty good sense of where Cliff and Didi are heading. Whether alone or together, they’ve grown more comfortable in their own skin, with a willingness, even an eagerness, to forge into the future.
The Baltimorons soundtrack is now available.
Author Bio:
Mark Orwoll writes about travel, film, and culture for Highbrow Magazine.
For Highbrow Magazine