Director Jay Duplass’ offbeat little charmer isn’t merely a rom-com focused on two lonely people who deserve better out of life; it’s also a love letter to Baltimore ... specifically, Baltimore on Christmas Eve.
No surprise, since Duplass co-wrote the script with Michael Strassner, who regards the city as his home turf.
As one-half of Duplass Brothers Productions, Jay and sibling Mark have delivered a string of off-beat indie films and television series, wearing multiple hats as directors, producers, writers and even actors. This is the first film Jay has directed in more than a decade.
He certainly hasn’t lost his touch.
The Baltimorons has echoes of Martin Scorsese’s darkly comic 1985 farce, After Hours, but with several key distinctions. Duplass’ touch here is much kinder and gentler, and the two primary characters are warm and relatable.
If not necessarily right away.
The saga opens with a fleeting prologue shocker, as an obviously inebriated Cliff (Michael Strassner) clumsily attempts to take his life.
Flash-forward half a year, to early Christmas Eve, as a now-sober Cliff makes plans to spend the day with the family of his fiancée, Brittany (Olivia Luccardi). She obviously has the patience of a saint, having nurtured and stood by him after the earlier crisis; that said, she’s also the worst sort of helicopter companion, monitoring his every choice and move, ensuring that he never again gets near any alcohol.
She even tracks his phone, and immediately calls if he’s not where she thinks he should be.
Luccardi plays her as compassionate and well-meaning, but also much too pushy. We understand her concern, but at the same time wince at her smothering attentiveness.
Poor Cliff, still guilty over what he put her through, accepts this hovering because he feels it’s the right thing to do ... but he’s clearly miserable. As introduced, Strassner makes him a large, forlorn teddy bear: shoulders slumped, morose expressions, forced smiles and wisecracks rather than serious conversations.
He comes by the latter naturally, since his longtime love is improv comedy. But Brittany has made him give that up, since it went hand-in-hand with his alcoholism; by way of catering to the demand that he find something else to do, Cliff is studying to be a mortgage broker. (Like that’ll ever happen.)
The point is, she’s forcing him to become something he finds alien ... and that isn’t a recipe for lifetime happiness.
En route to Brittany’s family gathering, Cliff clumsily face-plants after a chance fall on concrete steps, knocking out a tooth. This sudden emergency requires a dentist ... but where could anybody find one, on Christmas Eve?
He lucks out, after multiple phone calls, and secures an appointment. Driving quickly to the designated address, he’s surprised to see that his dentist is a woman: specifically Didi (Liz Larsen). Cliff nervously wisecracks his way into the chair, and we can tell — from Larsen’s rolling eyes — that Didi initially thinks he’ll be the patient from hell.
But his abruptly confessed fear — “What’s the needle situation?” — softens her mood, and she even grins wryly (out of his view) when his stream-of-consciousness rambling becomes mildly impertinent, after the application of nitrous oxide.
Truth be told, Cliff’s flirting isn’t entirely the result of the gas ... which speaks volumes about the true depth of his connection to Brittany.
And why is Didi available, on such short notice on Christmas Eve? Because her ex — “His name shall not be mentioned,” she warns, a bit later — is getting married to his new, younger hotsy fiancée on Christmas Eve, meaning Didi wil be reminded of this every holiday season.
The procedure completed, Cliff races back to where his car was parked — illegally — only to discover it has been towed. Didi grudgingly offers to drive him to the impound lot, and we’re off on a series of light-hearted misadventures, all of which serve to allow Cliff and Didi to learn more about each other.
And — no surprise — they even wind up at a pop-up improv comedy club, run by Cliff’s longtime friend Marvin (Rob Phoenix), who insists that his buddy reprise their famed “Baltimorons” sketch.
But a terrified Cliff isn’t sure he can do that, when sober.
Larsen is the perfect foil for Strassner, reacting to Cliff’s nervous, often befuddled antics with amused glances and mocking smiles. (Duplass and Strassner’s dialogue is note-perfect throughout.) But Didi’s gaze is constantly kind and friendly; it’s clear that she’s a good-hearted soul with her own streak of mischief, who’s ready for unexpected happiness ... even if it arrives in such an unlikely form. Frankly, she can’t resist Cliff’s mischievous energy.
All of this unfolds against numerous gaily decorated Baltimore neighborhoods and city pockets, transformed into an idealized romantic setting by Jonathan Bregel’s often soft-lensed cinematography. This cheerful atmosphere is enhanced further by pianist/composer Jordan Seigel’s jazz trio score, which opens the film with a reading of “O Tannenbaum” strongly in the vibe of Vince Guaraldi’s arrangement for A Charlie Brown Christmas.
After that beginning, how can we not adore what follows?

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