A return to form for Jay Duplass, who’s also making his solo-directing debut, The Baltimorons is a charming throwback to the low-budget indies he directed with his brother Mark. Written and starring burly stand-up comedian Michael Strassner, the Baltimore-set film follows the mis-adventures of an unlikely romantic duo: Strassner’s Cliff, a stand-up comedian six months sober, and his older workaholic dentist Didi (Liz Larsen). Cliff is bantering with his fiancée Brittany (Olivia Luccardi) when he falls and chips a tooth, sending him frantically searching for a dentist who will take him on Christmas Eve. Didi is the only one who takes his call, agreeing to meet him in her empty office for surgery.
Cliff is a silly teddy bear who aims to please even when he frequently oversteps the line into offending. He’s generously curious, often living life to acquire new material for stand-up. Like the personal lives of some filmmakers who often seem to be gathering material more than enjoying existence, Cliff always appears to be testing the waters. In this case, he’s perhaps playing a long game of “yes and” improv. The Baltimorons follows a similar structure, amping up both the embarrassment and sincerity.
Gathering new material isn’t exactly a bad thing, except for the fact he’s promised fiancée Brittany no more stand-up and, of course, no drinking. Yet, after the oral surgery, there’s plenty of material for a routine when Cliff’s car is towed to an impound lot and Didi agrees to drive him. Stalling his family dinner, Cliff takes it as a sign when Brittany gives him a free pass to get something to eat on his own once it starts getting late. He and Didi ultimately spend the day and night together when they try to find a restaurant with an open table in a hot neighborhood.
The film itself does not overstay its welcome, building sympathy for our lead character while fully using winter in Baltimore to create a portrait of characters down on their luck but ultimately happier together. Didi, divorced and newly a grandmother, doesn’t want her time wasted but is ultimately terrified at the prospect of spending the holidays alone and slowly becoming irrelevant to her daughter. When she brings Cliff to crash a holiday party, he performs masterfully on his feet in front of her ex-husband, the crabber Conway (Brian Mendes), and his more emotionally available new wife Patty (Mary Catherine Garrison). Despite the obvious pain of being present in the same room with family she’s distant from, the others can clearly see how Cliff and Didi make a compatible pairing.
Like The Puffy Chair and Cyrus, The Baltimorons is a charming and endearing throwback to mumblecore’s heyday, as well as the influential, gritty character studies of the 1970s. Even with his flaws, Cliff is ultimately a tender man who wants to do right by Brittany and Didi, at times trying too hard to be perfect. Inspired by Strassner’s own struggles, The Baltimorons holds awkwardness in a kind of perfect harmony. While the film may embrace a low-budget, drab-naturalistic aesthetic, it’s far from dull. Duplass, Strassner, and Larsen brilliantly execute one of the year’s finest romantic comedies.
The Baltimorons premiered at SXSW 2025.