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‘The Baltimorons’ Review: Jay Duplass’ Hilarious May/December After Hours Adventure Is A Super Winning Charmer [SXSW]

What if Martin Scorsese’sAfter Hours” was transformed from something less absurdly nihilistic and Kafka-esque and shifting towards the unexpected romantic comedy genre with a dash of May/December age and cultural differences on top to give it extra flavor and dimension? That’s not exactly what Jay Duplass’ excellent new comedy, “The Baltimorons,” is in total shape—you’d need to add some “Harold & Maude” and the general naturally sublime bittersweet shagginess of Hal Ashby films— but that description of this super eccentric and quirky picture is undoubtedly more accurate than your regular meet-cute romantic comedy.

A little zany, a little wild—sometimes shaped like a screwball comedy with similarly uproariously funny energy— and sweet and tender in all the right spots too, “The Baltimorons” centers on two lonely mismatched souls who unexpectedly cross paths, make a surprising connection and then meet at the ellipses and crossroads of something more, potentially romantic.

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The screwballness of “The Baltimorons” raises its head quickly; Cliff (a breakout Michael Strassner), a former comedian and recovering alcoholic only a few months sober, is trying to do right by his fiancée (a very convincing Olivia Luccardi, even in this small role). On his way to Christmas at his soon-to-be-mother-in-laws house, Cliff is clearly trying to impress that he’s better and not the f*ck up he appears to be on the surface.

But that notion quickly goes out the window when Cliff bites into a pie made for Christmas, cracks his tooth and rushes to a local dentist for emergency surgery. Running around town in pain, desperate to find anyone available on Christmas, Cliff eventually finds the offices of Didi (Liz Larsen), a 50-something divorcee who runs her dentist’s business and office.

Anxious, afraid of needles, and already a nervous chatterbox, Cliff’s verbal diarrhea makes dental surgery difficult, so she tries to dull his pain and subdue his manic energy with laughing gas. But it only begins to fuel a flirtatious side that seems to bud in Didi’s presence.

Overhearing in her office that Didi will have to spend Christmas alone because her ex-husband got suddenly married and the celebration is on Xmas Eve—and her daughter and granddaughter have to be there for the party—Cliff’s sense of empathy awakens, even in a drugged out stupor.

When he leaves the dental office to discover his car has been towed, Didi offers a ride to recover it, and a wild adventure between them begins.

‘The Baltimorons’ Review: Jay Duplass’ Hilarious May/December After Hours Adventure Is A Super Winning Charmer [SXSW]

Initially, Didi wants very little, if anything, to do with it—it’s just supposed to be a ride to the parking lot where towed cars reside, but it soon escalates into a hilarious snowballing of events that take them all over Baltimore that includes break-ins, excursions over town, an attempt at dinner,  a pop-in to her ex-husband’s house that surprises everyone there, a boat ride and a significant event at a dingy bar and comedy club.

This is the actual test of it all: a recovering alcoholic with dreams of a comedy career, the witty, quick-on-feet and charming Cliff has had to swear off the club to stay sober—and much of it at the behest of his long-suffering fiancée who keeps calling throughout the day to ask where the f*ck has he been and why isn’t he home for Christmas dinner yet??. Terrified and exhilarated by the club—wanting to return but not wanting to fall off the wagon and believing his comedy and booze go hand in hand, Cliff stops in to see old friends, but the moment soon turns into something more transformative.

Duplass’ movie is a total winner, though; extremely well-written, well-directed and certainly well-acted. Michael Strassner (“Modern Family”) is an incredible comedic discovery who needs to be filtered into the Hollywood comedic echelon immediately—he will make a great supporting character to start before his career surely ascends.

Likewise, Liz Larsen is terrific and very convincing as the skeptical, cynical and nearly bitter divorcee who is questioning why the hell this man, almost 20 years younger than her, is so kind, nice, and seemingly enamored with her long after the anesthesia has worn off. If actors like Edie Falco, Beverly D’Angelo, and Frances McDormand have had long and respected careers, there’s no reason to think why Larsen couldn’t have a similar trajectory.

Similarly, maybe the endearing Strassner is the more lovable, less hostile and caustic version of Danny McBride, and he should find no trouble entering the sphere of like-minded comedians.

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“The Baltimorons” is terrific and features an excellent mix of humor, sweetness, hijinks, hilarity, warmth, wistful melancholy, and charisma that’s off the charts, both in the actors and the movie itself.

Honestly, given how weak Sundance was this year, one can only surmise the reason “The Baltimorons” debuted at SXSW instead of in Utah is because of the long-standing relationship the Duplass brothers have with the Austin-based festival and because of its lack of star power.

But that should matter very little in the end because Strassner and Larsen are stars in the making; not A-listers mind you, they certainly won’t fit the bill of conventional stars. But beloved character actors and comedians in indies, drama and TV? Oh, hell, yes.

Jay Duplass has had a remarkable career as a character and supporting actor these last few years—see some exceptional work recently on season two of “Industry”—but “The Baltimorons” arguably demonstrates his true calling and part of it is outdoing almost every modern rom-com in ages. I’d take five more of these types of honeyed and appealing comedies in a heartbeat, so please, more of this, Jay. [A-]

Follow along for all our coverage of the 2025 SXSW Film & TV Festival.

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