Jay Duplass’ The Baltimorons is the kind of movie that starts amiable and amusing only to sneak up on you with surprising feeling. It’s been a remarkably strong year for small, handmade indies (Friendship, A Little Prayer, Splitsville, Twinless, Preparation for the Next Life), and Duplass’ film more than earns its place high among them. Following two lonely opposites who unexpectedly meet on Christmas Eve before tumbling into a sort of screwball odyssey, the picture moves with an easy, off-the-cuff charm until it becomes clear that Duplass and star/co-writer Michael Strasser have been digging at something deeper all along. One of the quiet joys of movies—if you see enough of them—is meeting characters you’re glad to have known, and happy to revisit over time. The Baltimorons is that kind of film.
The talented Duplass, who’s been making (and acting in) films and television during the two decades since he and brother Mark broke out with their microbudget 2005 comedy The Puffy Chair, teams here with Baltimore native and comedian Michael Strassner (Modern Family) for a winning picture about a troubled young comic and a caustic middle-aged dentist who stumble into something resembling friendship, and then more. Those diametric characters, named Cliff (Strasser) and Didi (Broadway veteran Liz Larsen), are hardly easy company: Cliff is fresh from a suicide attempt and clinging to sobriety, while Didi, a divorcée, masks her disappointments behind a brusque front. Yet in the hands of such gifted performers, they become special company indeed.
When we first meet the teddy bear–like Strassner, his Cliff is staging a hapless, failed suicide attempt. Flash forward six months to Christmas Eve morning, and he’s heading to brunch at his future mother-in-law’s with fiancée Brittany (Olivia Luccardi). In just a few strokes, Duplass smartly sketches the strain in their relationship: Brittany constantly managing Cliff’s anxieties, worried he’ll relapse if he returns to open-mic comedy, their bond already too brittle for such a hopeful young couple.
When Cliff accidentally chips a tooth, he races across town for help and ends up at the only dentist’s office still open, run by Liz—who’s hardly thrilled to face an emergency just as her own holiday begins. “What’s wrong with you?” Liz asks. “Everything,” Cliff replies. That’s an understatement. This prickly meet-cute lands with big, needle-phobic laughs, but sharpens when Liz’s adult daughter chooses to spend Christmas with her newly re-married father, leaving her without plans.
After Cliff parks in a tow zone, Liz—against her better judgment—offers him a ride to the pound. From there, things don’t exactly calm down. The two end up zig-zagging across Baltimore, caught in one small fiasco after another, the comedy always undercut by these little flashes of kindred recognition. As night falls, both have eased up, just a little, letting their guarded selves slip through. And by the time this movie gets where it’s going, we’ve seen a offbeat romantic comedy with real-world implications for two not-so-happy people we’ve really fallen for over the course of 90 concentrated minutes.
Duplass stages some wonderfully off-kilter moments that deliver big laughs, including that auto pound car rescue and the theft of a crab boat, but what really hits home are the human ones, namely an impromptu visit to Liz’s ex’s home which turns out not to be as painfully awkward as we’d expect, and a charmer in which Cliff and Liz take the improv stage as unlikely “yes, and?” scene partners, sparking a real connection between their much needed ports in a lonely holiday storm.

That scene is arguably the film’s apex—Cliff re-embraces his identity as an artist (he’s a former member of Baltimore’s premiere improv comedy ensemble) and faces down his demons since stepping into the club is an invitation back to the bottle that sent him spiraling. The moment Liz joins him onstage is riotously unexpected.
And then comes a standout scene between Cliff and Brittany, a long-delayed heart-to-heart about how their relationship is coming apart and if they have a future, written with sensitivity to their individual perspectives and needs. These are loving people in a thorny situation who care for each other—even if their love story can’t last.
In nearly every scene, Strassner, with terrifically deadpan neuroses, bounces beautifully off Larsen, who plays the straight man with just the right mix of patience and bite. At first their match feels unlikely as they seem to be from entirely different worlds (both in character and performance), making its hard to imagine a bond developing from such jittery beginnings. But somewhere amidst this two-handed Baltimore road movie you end up really wanting them together. Cliff and Didi are two people stuck in neutral who had plans for life that dramatically fell apart, so what now? Neither of their lives make sense to them but maybe together they do.
Duplass and Strassner have penned a very funny dual character study, giving us just enough of Cliff’s substance issues and shaky psychology to make him empathetic, without letting the story sink under the weight of any issues. And Liz feels authentic, written with just the right balance: nothing shocks her, but there’s enough vulnerability in her to pull us closer. The skilled Larsen performs with a effective, gradually melting cynicism. And Strassner gives one of the year’s great comic performances—he can get belly laughs, sure, but he is always open and alive. While he might initially appear to belong to the Belushi-Farley-Galifianakis tradition, there’s real substance underneath.
Made on a shoestring, The Baltimorons is one of the year’s true sleepers: laugh-out-loud funny yet steeped in compassion for its prickly characters, who—like the best holiday misfits—carry their misgivings right up until they find unexpected meaning in each other. That distributor IFC is giving it a limited release makes sense in today’s market (no big stars, no high concept), but it’s the kind of film that anyone can love. With a bit of luck, it’ll get Independent Spirit Award attention next year and go on to become the sort of holiday favorite we hold dear each Christmas.
3 1/2 stars