‘The Baltimorons’ Review: Jay Duplass’ May-December Romance Is a Stealth Charmer With a Low-Key ‘After Hours’ Vibe

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Following collaboration on several low-budget independent films with his brother Mark and over a decade in television production, Jay Duplass presents his understated first solo directorial effort with “The Baltimorons“. Infused with a subtle thread of melancholy and spontaneous humor, the movie chronicles a thirty-something, recovering ex-improvisational comedian who damages a tooth on Christmas Eve, necessitating immediate dental attention. This sets in motion an unexpected romance. The storyline could have easily veered into cheesy territory, but the actors breathe authenticity into it, making it surprisingly touching.

Beyond his acting and producing roles, Duplass has been primarily engaged in directing TV episodes since 2015, notably on shows like “Togetherness”, “Search Party”, and more recently, “Somebody Somewhere”. I’m still upset about the lack of Emmy recognition for that consistently excellent show. Similar to how “Somebody Somewhere” was crafted with deep character understanding around its lead, Bridget Everett, the core structure for “The Baltimorons” is built on co-writer and main actor Michael Strassner. He’s partnered with the talented Liz Larsen in a heartfelt May-December romance.

The film presents two contrasting characters who form an unlikely bond, aiding each other in ways they hadn’t managed on their own paths. While the plotline might appear formulaic, it’s refreshingly genuine, avoiding common traps of overwrought sincerity or cloying sentimentality. This is largely due to exceptional acting chemistry between the leads and the director’s deft, subtle handling. Moreover, Baltimore serves as a passionate backdrop for this story, showcasing its working-class neighborhoods and harbor with an authentic, heartfelt affection.

In the initial sequence, Strassner is depicted climbing the stairs towards his attic, setting up a chair beneath a rafter and crafting a noose from his belt. His sluggish movements hint at a series of setbacks, making it seem as though he himself is not shocked by his failed suicide attempt. Fast forward to six months later, where Strassner timidly exhibits his sobriety anniversary medal to Brittany, his cautious girlfriend, who remains ever watchful. (Olivia Luccardi portrays Brittany.)

When Cliff mentions that his friend Marvin (Rob Phoenix) is performing stand-up that evening and invited him, Brittany recoils, urging him to steer clear of scenarios that could lead him to revert to past behaviors. He had pledged to her – no more alcohol and no more comedy performances.

Upon reaching Brittany’s mother’s home for a family dinner, Cliff accidentally crashes into the door frame, resulting in a broken tooth and a mouthful of blood. Since most dentists are closed during the holiday, it takes some time before he receives a reply from Didi (Larsen), a practical woman who is unfazed by his jokes or romantic advances. In the end, she manages to fix his tooth temporarily with a filling.

Overhearing Didi’s distressing phone call about her daughter skipping dinner for her new stepmother’s celebration, I found myself in quite a pickle when my car was towed later that day. Luckily, Didi, who showed genuine concern, offered to drive me to the impound lot and came to my rescue once again when we discovered it was closed.

At the outset, Duplass sets the season with piano-bar melodies by composer Jordan Seigel, reminiscent of holiday favorites such as “O Christmas Tree” and “Jingle Bells.” As the narrative progresses, the music transitions into lively jazz rhythms, maintaining a breezy atmosphere as Didi gradually lowers her defenses and grows fond of the unpolished, frank character named Cliff.

He admits that he reluctantly abandoned his dreams of becoming a comedian and is now trying to become a mortgage broker, while she confesses that she’s a workaholic whose marriage to her high school sweetheart turned sour. Di diplomatically refuses when Cliff invites her for dinner as a gesture of thanks. However, he manages to break through her defensive barriers, and gradually, as sparks of mutual attraction begin to emerge, the significant age gap between them (spanning a few decades) appears less noticeable.

The subdued ambiance of the tow yard gradually intensifies as they explore restaurants open for Christmas Eve. Cliff encourages Didi to attend a gathering where her former spouse Conway (Brian Mendes), along with his wife Patty (Mary Catherine Garrison from ‘Somebody Somewhere’), are celebrating, joined by Didi’s daughter Shelby (Jessie Cohen) and granddaughter Maddie (Zoe Strassner).

As the quiet atmosphere of the tow yard evolves, they investigate restaurants open for Christmas Eve. Cliff inspires Didi to go to a party where her ex-husband Conway (Brian Mendes) and his wife Patty (Mary Catherine Garrison from ‘Somebody Somewhere’) are celebrating with Didi’s daughter Shelby (Jessie Cohen) and granddaughter Maddie (Zoe Strassner).

In a particularly humorous moment from the film, Cliff employs his talent for improvisation as “Didi’s charming young companion.” He invents outlandish stories to flatter her and prolong the deception towards Conway and Patty.

After a small win under my belt, I found myself eager to support Marvin at his impromptu comedy gig – an improvised night right in an old auto shop. This was where Marvin would share the story of his downfall and the anxieties that came with revisiting this place for the first time since he’d achieved sobriety.

Duplass and Strassner’s screenplay subtly depicts the rollercoaster ride of the protagonists’ relationship development throughout the story, avoiding any unrealistic or implausible moments, not excluding their unexpected late-night crabbing adventure on a lent vessel.

A striking moment unfolds as Cliff faces off with Brittany, a situation that transitions from rage to heartfelt sincerity, showing empathy towards both individuals. In Cliff’s confession, there’s a sense of remorse and longing for forgiveness: “I’ve attempted to live the ordinary life, but it just doesn’t suit me.” Brittany responds with grace and dignity, accepting Cliff for who he truly is.

Although the film’s cold color palette and dark outdoor night shots create a somewhat dull, gritty appearance, it is enlivened by the heartwarming human connections hinted at through its humorous dialogue.

Duplass skillfully avoids falling into typical romantic comedy tropes, ensuring that every scene, like when Cliff asks Didi to dance to her wedding song “Someone to Watch Over Me,” feels genuine and fitting for the characters and the situation. By the end, we’re unsure about Cliff and Didi’s future together, but through delicate storytelling, The Baltimorons hints that both have grown and improved from their initial circumstances.

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2025-03-09 04:54