The Baltimorons - Review from the Chicago Critics Film Festival 2025

      The Baltimorons, 2025.

      Directed by Jay Duplass.

      Featuring Michael Strassner, Liz Larson, Olivia Luccardi, Jessie Cohen, Brian Mendes, Marina Erickson, Stacy Caspari, Morgan Dixon, Zoe Strassner, Drew Limon, Rob Phoenix, Chris Strassner, David Strassner, and Mary Catherine Garrison.

      SYNOPSIS:

      On Christmas Eve, a man in recovery faces a dental emergency that unexpectedly blossoms into a romance with his older dentist as they navigate Baltimore together. Sometimes, the worst pain and the most challenging days can lead to profound clarity.

      Cliff, a thirty-something recovering alcoholic played with a mix of charm and vulnerability by co-writer/star Michael Strassner, is grappling with the decision to return to sketch comedy, which he used to pursue with a group called the Baltimorons. His texts to a stand-up comedian friend indicate a desire to return, but his fiancée (Olivia Luccardi) is understandably anxious about his return to that world following his suicide attempt—a true event from Strassner's life that is skillfully woven into this touching holiday story set in Baltimore.

      The central question of co-writer/director Jay Duplass’ (marking his first feature-length solo directorial effort) The Baltimorons revolves around whether Cliff believes he can face the risk of relapse and whether he can summon the courage to try. It is evident that he feels unfulfilled in his personal life, struggling with the relationship dynamics as they plan for a future together, although he seems uncertain about starting a family. His occasional slip-ups, such as referring to his fiancée as a girlfriend, reflect this uncertainty.

      Before the Christmas Eve dinner at his fiancée’s family home, Cliff accidentally injures himself, breaking a tooth and needing immediate dental care. Fortunately, he finds a dentist in Didi (Liz Larsen), who is older, charming, and emotionally complex—also navigating her own challenging circumstances. Didi is working over the holidays, possibly as a distraction from her family issues, which include her ex-husband’s new relationship and a recent wedding announcement from her daughter.

      Michael Strassner’s physical comedy brings a youthful energy reminiscent of John Belushi, and from the outset, it’s clear that this film is a unique gem. Jay Duplass and Michael Strassner deliver a hilariously entertaining dentist appointment scene where humor serves to deepen character understanding. At times, Cliff’s attempts to guess the names of Didi’s relatives are simply absurd, adding to the film's charm.

      Cliff and Didi embark on a journey through Baltimore filled with humorous and poignant moments, prompting both characters to confront their pasts and their aspirations. While romance certainly exists amidst the age difference, the film deeply delves into their personal lives, showcasing a thoughtful exploration of their experiences.

      A witty comedy of errors, a tender May/December romance, a deeply personal examination of mental health, and a sensitive take on alcoholism highlighting the fine line between joy and self-destructive behavior, The Baltimorons is anything but foolish. It’s rich in depth and authenticity, featuring a hilarious Baltimore Ravens joke along with a genuine affection for the city.

      Flickering Myth Rating – Film: ★ ★ ★ ★ / Movie: ★ ★ ★ ★

      Robert Kojder is a member of the Chicago Film Critics Association, Critics Choice Association, and Online Film Critics Society. He serves as the Reviews Editor at Flickering Myth. Check here for new reviews and follow my BlueSky or Letterboxd.