Rating: R | Runtime: 101 minutes
Release Date: September 5th, 2025 (USA)
Studio: IFC Films
Director(s): Jay Duplass
Writer(s): Jay Duplass & Michael Strassner

Super thrilled to be here!

I didn’t realize there was an endearment test until Cliff Cashion (Michael Strassner) introduces himself by his whole name, to the same room, a third time. It’s a maneuver usually ascribed to blowhard traveling salesmen weaponizing every breath to stay relevant and hook new clients. The sort of thing that makes you instinctively cringe whenever it occurs. And yet Cliff’s smile and genuine enthusiasm provides an earnest innocence that makes you want to give him a hug. Even if it’s a bit he doesn’t realize he’s doing because his improv brain just takes over, you could never be angry. You also want everyone to remember his name.

It’s the same energy Matty Matheson exudes as Neil Fak on “The Bear”—that teddy bear mystique of joviality proving so pure that it makes the uncommon frown pierce your heart due to its sorrow being amplified by the absence of a smile. And since Jay Duplass’ The Baltimorons opens with a suicide attempt gone wrong, that contrast is a huge piece of its success. Strassner (who co-wrote with Duplass) maintains an underlying thread of sadness with the character because he’s always one roadblock away from feeling that despair again. It’s why he didn’t just give up drinking after almost ending his life. He relinquished his identity.

What’s great about the script, though, is that it never blames Cliff’s fiancé Brittany (Olivia Luccardi) for this decision. Yes, her love and worry trigger his quest for sobriety and his desire to dedicate himself to being present in their relationship demands he leave everything connected to that behavior behind (his sketch comedy aspirations), but that doesn’t make her a villain. It’s problematic that she isn’t willing to give-up a binary all-or-nothing mindset to the point of making him promise to never try and get back into that life without the alcohol, but it’s ultimately on Cliff to have that conversation.

So, one must ask: does Cliff even want to try that? How much of his pivot into “normalcy” as a prospective mortgage broker is using Brittany’s push as an excuse to ignore his own fear? It’s why slamming his face into a door and losing a molar becomes an unlikely Christmas miracle wherein he’s forced to confront the possibility he’s course corrected too far. And it’s not just because the injury allows him to meet Dr. Didi (Liz Larsen) and want to help make her smile after eavesdropping on how horrible her Christmas Eve has gone. But also to learn how his lack of communication with Brittany has made their problems worse.

All Cliff needs to be happy is a “yes and …” partner. He tries with Brittany, but she’s too busy with family to even save him a plate for his return from emergency dental surgery. So, he tries getting it from Didi too, but she has her own problems and babysitting this giant child—while entertaining—would only become an excuse to avoid them. It’s therefore only when shared kindness drags her and Cliff into committing a felony together that the distraction from their tailspinning lives might reveal itself to be a balm instead. Maybe if they give each other this reprieve today, they’ll heal enough to deal with the chaos tomorrow.

It’s an extremely charming ride that starts with the two deciding it’s okay to wallow together and at least have some company now that they’ve both been abandoned. With every new scenario Duplass and Strassner throw at these characters, however, we soon realize the whole of The Baltimorons is pretty much just an extended rendition of that titular sketch in Cliff’s repertoire. Procuring his car from impound. Crashing her ex-husband’s wedding reception. Actually going on stage to perform said act sans safety rails (Didi has never been on stage before and Cliff has never done it sober).

Each step leads to an epiphany that they no longer want to sulk alone. Didi is obviously skeptical that he truly wants to hang out with her (he’s much younger and has a fiancé), but the electricity and excitement that comes from being appreciated and thought about rejuvenates her desire to cause trouble. And once she opens up enough to reveal this fact, Cliff is never going to let go. She wants to watch a comedy show? She wants him to be unhinged? He’s really being this charismatic and magnetic without the booze? These are two lost souls who, even if just for one day, have remembered what it means to be themselves.

And that, of course, also means that Cliff must reveal the circumstances that got him here. We know why Didi has lost that spark, but why Cliff? Well, it’s as tragic as you’d expect considering the suicide attempt, but it gets even more heart-breaking well after you believe you already have all the details. That’s a testament to Strassner’s performance and a script that knows how to use comedy as a tool to mine down into the abyss and expose an authentic truth. Funny people can hurt and straight-faced professionals can know how to have fun. Finding the honesty to admit and show those realities ultimately comes down to trust.

That’s what Strassner and Larsen’s chemistry delivers. Sure, there’s romance and kinship, but the plot’s progression coincides with character evolutions too as Didi thaws and Cliff stiffens until a release can occur. It results in a memorably complex and mature rom com that gets the appeal of friendship and camaraderie within the “love” equation. Whether this relationship is consummated or broken off doesn’t matter because nothing that happens physically could ever compare to what they share emotionally. Together or apart … it won’t change how this day has become a crucial turning point for the rest of their lives.

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Liz Larsen and Michael Strassner in Jay Duplass’s THE BALTIMORONS. Courtesy of Jon Bregel. An Independent Film Company Release.