The Baltimorons, 2025.
Directed by Jay Duplass.
Starring Michael Strassner, Liz Larson, Olivia Luccardi, Jessie Cohen, Brian Mendes, Marina Erickson, Stacy Caspari, Morgan Dixon, Zoe Strassner, Drew Limon, Rob Phoenix, Chris Strassner, David Strassner, and Mary Catherine Garrison.
SYNOPSIS:
A newly sober man’s Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.
Sometimes, terrible agonizing pain and what feels like it will be the worst day ever gives way to beautiful clarity.
Thirty-something Cliff (played as a lovable goof, harmless idiot, and achingly human by co-writer/star Michael Strassner, which is not an easy combination to pull off) is a six-month-sober recovering alcoholic conflicted about returning to his passion: sketch comedy, where he was once part of a troupe known as the titular Baltimorons. Evidently, by text messages to his stand-up comedian friend, he wants to do it.
However, his fiancée (Olivia Luccardi), while proud of his recovering alcoholism in the wake of a suicide attempt (a real-life incident for Michael Strassner with the only reason he is still alive boldly played for a dark laugh, also used as a launching pad for this heartfelt, moving christmastime odyssey around Baltimore) is, presumably justifiably, paranoid that stepping back into that scene will cause a relapse.
The question at the heart of co-writer/director Jay Duplass’ (making his feature-length solo directorial debut) The Baltimorons seems to be whether or not even Cliff thinks that’s possible, and if he can build the courage to try. It’s also made clear that he doesn’t feel fulfilled in his personal life and that aspects of this relationship are rocky, with him perhaps having jumped into something long-term with plans of starting a family, unsure if that’s something he even wants. He sometimes accidentally refers to his partner as a girlfriend instead of a fiancée, which is telling of that.
Nevertheless, Cliff inadvertently walks into the wall while trying to enter his fiancée’s family’s home in preparation for a Christmas Eve dinner celebration, cracking a tooth and immediately requiring dental assistance. Miraculously, he does find one in Didi (Liz Larsen, charming, simultaneously bold yet emotionally vulnerable, and similarly going through a rough personal patch), a workaholic somewhat older than him, open for the holidays, possibly not only for love of the job, but as a distraction from familial chaos. Her ex-husband is with a younger woman, and her daughter has just phoned her to let her know they just got married at the courthouse and that there will be a celebration later on that she is invited to attend.
Aside from the howlingly funny physical comedy from Michael Strassner, who at times evokes the presence of a young John Belushi, it’s apparent from early on that this is a special little gem, as Jay Duplass and Michael Strassner stage a highly amusing dentist appointment scene that, much like the majority of the jokes here, uses laughter as a means to reveal more about the characters. Sometimes, it’s also plain silly for Cliff to try to guess the names of Didi’s relatives for no reason or with no filter.
Cliff’s personal drama and persistence push Cliff and Didi on a journey through Baltimore, complete with more hijinks and moving situations, forcing both to confront aspects of their past and who they want to be in the present, making it almost Dickensian. Yes, romance is in the air despite the age gap, but this is also a film concerned with their personal lives just as much, contributing to the sincere thoughtfulness on display.
A hilarious comedy of errors, a sweet May/December story, a profoundly personal treatise on mental health and the importance of personal fulfillment, and a thoughtful approach to alcoholism while sensitively observing how dangerously tempting it can be that the things that make us happy just are sometimes adjacent to self-destructive vices, The Baltimorons is far from moronic. It’s layered and lived-in, boasting a laugh-out-loud Baltimore Ravens joke and more love for the city.
Flickering Myth Rating – Film: ★ ★ ★ ★ / Movie: ★ ★ ★ ★
Robert Kojder is a member of the Chicago Film Critics Association, Critics Choice Association, and Online Film Critics Society. He is also the Flickering Myth Reviews Editor. Check here for new reviews and follow my BlueSky or Letterboxd
Originally published September 4, 2025. Updated September 5, 2025.
