The Baltimorons
"Well, I guess that makes me the Ghost of Christmas Present. Cliff Cashen, still really really thrilled to be here, gang. Thank you."

Everything about The Baltimorons is descended from an instantly recognizable tradition. It's a low-budget, Sundance-inflected indie that owes a lot to mumblecore. It was shot on 35mm film, so every single frame is soft and cozy and warm, no matter how cold the color palette (or outside temperature) becomes. The accompanying score is jaunty and jazzy, although the movie isn't afraid to cut it out entirely to let the drama breathe. Neither lead is a well-established feature film actor, nor do they look quite like most who are, but both have been around. Both protagonists, Cliff (Michael Strassner) and Didi (Liz Larsen), are horribly lost souls searching for the light despite their initial belief that they're content, if not exactly "happy". They find each other through a contrived yet not implausible scenario. Despite some initial resistance, circumstances keep bringing them together, until they relent and go on a low-key adventure over a short time-period. As it unfolds, they make a series of decisions that surprise even them, but result in a magical time that neither wants to end. Their world explodes into technicolor, even as they feel comfortable enough with each other to open up about some truly dark subjects. It culminates in the real world crashing in on their party. They leave the experience somehow less certain about what the future holds than before, but far more prepared to face it.
All of that is before you consider that it takes place on Christmas Eve, making comparisons to The Holdovers inevitable, despite their wildly different plots.
But that just proves the inadequacy of evaluating success purely on uniqueness. Writer/director Jay Duplass' screenplay (which he co-wrote with Strassner) crackles with life, full of an infectious energy and joy despite being undergirded by sadness. While Cliff is a (recovering) comedian by trade, Didi brings more than her fair share of humor to their interactions. Which is important, as she initially comes off somewhat cold and closed off while vociferously refusing the call to adventure. Duplass smartly provides some insight into her defeated demeanor right away, helping to explain her insistence on withdrawing. Similarly, the movie opens with a darkly comedic scene that shows why Cliff is so desperate for connection. Both are simple and well-trodden, but ground us in how broken the protagonists are, properly situating us for the journey ahead.
For most films, this rigid adherence to the familiar would be a weakness. And there are absolutely moments when that proves to be the case. Many scenes skirt the edge of being a filmed stage play, and a few clearly exist purely as padding. But The Baltimorons gets away with it because it quickly and effectively shifts the focus off the plot. There aren't any mysteries for us to get wrapped up in, nor some grand spectacle to get worked up for. Even their swapping of life stories simply deepens our understanding of emotional damage we were already aware of. What we're left with are two very well lived-in characters performed beautifully. Their chemistry jumps off the screen, and they wear their hearts on their sleeves for us to see, despite their coy shielding of it from each other.
The downside of such an approach is that you either like it or you don't. While it explores some of the ways stepping out of your comfort zone can radically alter your perspective on your life (a novel concept, I know), it's really all about their rapport. Duplass relies on Strassner and Larsen to sell the screenplay's "quirky" sense of humor by embodying the natural awkwardness and ease of two real people, a role both are more than up to. However, if you're allergic to this mode of storytelling, or if the humor doesn't land for you, or if you need there to be more going on than "two lonely people wander around town", there isn't going to be much here for you.
Even for those of us on board with what it's doing would be hard-pressed to say it nails every element. There are a few dramatic beats it tries to hit but never figures out, such as a performance of the titular improv routine. At least that one manages to keep you laughing throughout. But the biggest and more cringeworthy miss is the characterization of Brittany (Olivia Luccardi). The screenplay needs to establish why Cliff allowed himself to abandon his fiancé on a major holiday to spend the day with a stranger. Not necessarily to justify why it's okay; explanation does not equal endorsement. But to add to our understanding of the character. Unfortunately, she's written as an old, tired stereotype. She comes into her key scene (she's only in two or three) guns blazing, already furious with him, uninterested in chatting. Her only desire is to scold him like a child, to guilt-trip him with her concern, to hold his recent history with alcohol and depression against him. Most egregious is her chastising him for performing comedy due to its connection to that history. It lays bare its existence as a screenwriting device to cement her as an obstacle, given we just saw how positive and healing that return to what he loved was for him. To be clear, none of this is a blemish on Luccardi's performance, which brings a pained humanity to Brittany's anger. But it can't save what is ultimately a scene designed to give Cliff permission to act however he wishes.
A single scene has a hard time sinking a movie, but when the crux of the film is the emotional throughline of the characters, it can damper it. It represents a drastic alteration of Cliff's experience and responsibilities, which cannot help but shape the audience's reception of the narrative. The conflict has been muted, making future ambiguity more of a reflection of the character's internal life than an uncertainty how to reconcile the different parts of him. So the ending is robbed of the ability to land with the resounding and satisfying thud that seems intended. Instead, we're left with a misshapen Christmas classic, a heartwarming comedy that stumbles in its attempts to outrun its cliches, and a warm hug of a film that carries a whiff of personal resentment.