The Baltimorons
Cliff Cashen (Michael Strassner) is navigating his way back into life after an unsuccessful suicide attempt and six months of sobriety, but his fiancée, Brittany (Olivia Luccardi, "It Follows"), associates his old comedic improv work with the road to ruin, alarmed by his friend Marvin's (Rob Phoenix) texts that he will 'see him tonight,' something Cliff readily denies. But when he slips on his future mother-in-law's stoop on his way in for her Christmas Eve spread, an emergency trip to the only dentist who will respond, Didi (Liz Larsen), will end up with both of them performing his most famous bit, "The Baltimorons."
Laura's Review: B+
After not directing a film with or without his brother Mark for ten years having turned to acting and producing, cowriter (with star Michael Strassner)/director Jay Duplass ("The Puffy Chair," "Cyrus") returns with a big-hearted, quirky holiday rom com destined to become a Christmas classic.
After following Strassner on Instagram, Duplass guided him through a short film before collaborating on this, a truly affecting May September romance between two people with similar comic sensibilities left out in the cold on Christmas Eve. Kudos to Duplass on casting, as he also found Larsen in the Broadway musical version of 'Transparent,' and if the two costars are relatively unknown now (they resemble a young Jon Favreau and older Ari Graynor), this movie should go a long way towards changing that.
Cliff arrives at Didi's office holding a rag to his mouth and the young guy afraid of needles is handled brusquely by the older woman. But Cliff gets silly under the influence of nitrous and his natural tendency to make connections starts to have an effect, beginning with his penchant for guessing people's names. The doctor remains doctor for a while, though, but when Cliff overhears her take a phone call from her daughter informing her that her ex-husband remarried that morning and is having the reception that very evening at his home, Cliff insists on taking her to dinner. She insists otherwise, but when she finds him out on the street, his car having been towed, she offers to drive him to the tow yard and thus begins their adventures.
This is one of those films where a couple converses and acts impulsively over the course of an entire evening. Cliff asks Didi to make a detour on the way to the car lot to get her to try his sweet potato casserole (as usual, she needs a lot of prodding). He then ends up getting locked inside the tow lot, so Didi gets him out with bolt cutters. She finally agrees to dinner, but by the time Cliff actually finds a place that will take them on a holiday eve, she realizes she's only two blocks from her ex's and decides to join the family, wanting to see her daughter Shelby (Jessie Cohen) and granddaughter Maddie (Zoe Strassner). Cliff is a huge hit with newlyweds Conway (Brian Mendes) and Patty (Mary Catherine Garrison, HBO's 'Somebody Somewhere') and an even bigger hit with Didi when his offer to get her ex and his wife into a 'box' for a Ravens game was just him doing pranky improv. That's what leads Didi to ask him to take her to a show and when Marvin announces Cliff will take the stage and he demurs, Didi insists. What happens there is magic almost derailed by a misunderstanding, followed by Didi jacking Conway's crab boat. That last adventure causes yet another, more serious misunderstanding, Cliff's fiancée waiting for them in a panic when they return to the dock.
Strassner is a lovable teddy bear type whose confidence grows the longer he is in Didi's company, his early low self esteem bolstered by her comment - 'You have a great face' - one which he returns. This they both do, the camera loving his oversized, shaggy openness and her petite blonde with a smile that lights up a room (and evens out her biting humor). Here's a couple with a generational age difference we quickly forget, the actors convincing absolutely these two belong together, Strassner and Duplass's witty, relatable banter sealing the deal. The Christmas holiday, reflected around Baltimore streets and neighborhoods, adds to the film's warmth, composer Jordan Seigel (2025's "Snow White") using the same jazz-inflected Christmas classics that Vince Guaraldi did for 'A Charlie Brown Christmas.' Baltimore, too, is given its due, not only with Ravens fanaticism but crab balls, apparently a Christmas staple, that boat ride an excursion to quell Didi's desire for soft shells. Duplass and his director of photography Jon Bregel give us a city of both grit and coastal allure, its personality akin to the love affair flourishing there.
"The Baltimorons" is a movie to embrace - it has charm to spare, two breakout performances and the welcome return of Jay Duplass in the director's chair.
Robin's Review: B
Recovering alcoholic and former stand-up comic Cliff (Michael Strassner) has a fall and breaks a tooth - and it is Christmas Eve. He calls every dentist in town and they are all unavailable, except for Dr. Didi (Liz Larson), who agrees to treat him. But, things get more complicated than just a broken tooth in “The Baltimorons.”
When I sat down and began watching director Jay Duplass’s latest opus, written with his star Strassner, I was turned off by the Cliff character. He is selfish and not aware of his selfishness on those around him. Fortunately, once the tooth is broken and Dr. Didi comes into the picture, the story turns into a thoughtful Christmas comedy about two lonely people thrust together on one of the most family-intensive holidays of the year.
After Dr D does her job and temporarily fixes the broken tooth, they make a follow up appointment and part ways. Cliff’s car, though, has been towed and the doctor reluctantly offers him a ride. This is where the bonding begins and an odd June/September relationship buds into life.
But, it is Christmas and Didi both have family problems. Cliff’s former drinking has tainted his relationship with his fiancée, Britanny (Olivia Luccardi), while Didi’s daughter is having a wedding celebration for Didi’s ex-husband and his new wife. Talk about two sad sacks.
Cliff, though, as a former stand-up comic - he could only perform drunk and gave up the stage after he became sober – knows a lot of people and places. He tries to use his “influence” to get them into a bar or a restaurant. He is only a little successful but, for Didi and Cliff it is a brand new adventure with an unlikely brand new friend, making for a solid Christmas movie.
Michael Strassner’s Cliff is annoying as heck when you meet him. He is a needy person and pushes himself on his new dentist. He has a good arc of character, though, and develops into a 3D person as the story plays out. The older Didi does not go through a similar transformation. Instead, we watch a fully formed adult suddenly realize that all the problems in her life were not all HER problems.
The odd couple relationship we have here never rings false and there is real, funny comedy throughout and a believable friendship develops between Didi and Cliff. In the end, I wish a heartfelt “Merry Christmas” to them both.
The Independent Film Company releases "The Baltimorons" in select theaters on 9/5/25, expanding on 9/12/25.
