The Baltimorons

Over the past couple of decades, Jay Duplass has come to dominate a certain type of deceptively haphazard comedy, in which messy, damaged characters stumble through mundane scenarios and find something magical in the process. The Baltimorons is one of his best works to date (produced, as usual, by his brother Mark Duplass). The story of a Christmas Eve on which nothing goes to plan, it brings two very different characters together for an adventure which just might give way to romance.

Cliff (Michael Strassner) is a recovering alcoholic who has burned many bridges in the past but is determined to enjoy Christmas with his family when he returns home to Baltimore. Unfortunately things don’t go to plan, and he finds himself stumbling round the city in a desperate search for an emergency dentist whose surgery is open despite the holiday. Enter Didi (Liz Larsen), who brings tremendous relief just by doing her job, which is perhaps what initially prompts Cliff to get excited about her. After receiving treatment, he wants to take her out and thank her properly. Despite his blatant flirtation, she doesn’t take him seriously as a romantic prospect, in part because he’s quite a bit younger than her and in part because he’s such a chaotic mess. Nevertheless, though she does her best to fend him off, they end up spending time together, with one thing leading to another as day turns into night and the initially quiet streets fill up with revellers.

Some viewers – especially women – may feel disquieted by the idea of watching a man bother somebody at work and then follow her around trying to persuade her to like him despite her objections. Key to the success of The Baltimorons is that it never pretends this is okay. Cliff is a broken person who is not behaving rationally or reasonably. Didi’s efforts to escape are treated with sympathy – and yet, she, too, has her troubles. Her better coping skills cannot permanently conceal her unhappiness, and the awkward, overly cautious way in which she approaches life isn’t helping with that. Cliff’s chaos may be just what she needs. The connection that forms between them feels more real because it’s so unlikely. Duplass, co-writing with Strassner, has the skill to pull it off, and both lead actors are up to the task.

What makes the film compelling to watch is partly the fragility of this connection, which will make you perpetually uncertain as to how things will turn out, and partly the comedy which emerges in the course of their adventures, as Didi begins to let go and Cliff finds a way to balance his desire to have fun with his need to protect his sobriety. It’s warm-hearted and spontaneous, easy to engage with. At the same time, it gradually becomes apparent that the impulsive nature of Cliff’s romantic expressions, and even his friendliness, are part and parcel of his experience as an addict. His charm is tangled up with a desperate vulnerability which is a lot for anybody to take on. Didi is old enough and wise enough to recognise this. Enjoying one wild night on the streets of Baltimore is a very different proposition from maintaining a connection which will inevitably encompass pain.

Jonathan Bregel’s cinematography brings out the beauty in urban landscapes by day and by night, without sentimentalising them. The people are very much a part of the landscape during the night-time scenes. Duplass is a great director of ensembles and the supporting performances are spot on at a party and a comedy club where Cliff and Didi spend time. Notably, each individual seems to be caught up in their own story, with their own things going on, intersecting with the protagonists but never pushing them to centre stage. This enables us to see Cliff and Didi’s developing bond as just one part of a larger tapestry of city life. The implication is that we could wander off with any one of these additional characters and find them equally interesting upon getting to know them.

Invited into this sprawling and yet intimate space, we might have a number of hopes for the central pair, but what is clear from the beginning is that whatever happens, this will be a night to remember – for us as well. A film you’ll be keen yo return to when you need a little more warmth in your life, The Baltimorons is a real treat.

Reviewed on: 25 Feb 2026