Philip Seymour Hoffman debuts his directing skills with a story about a limo driver whose life isn’t as prosperous as it should be. Hoffman also performs in the film’s lead role, the titular Jack. Jack doesn’t have a bad life but it’s obvious to everyone around him that it could be better. When he’s introduced to a peculiar but sweet woman named Connie (Amy Ryan), the drive he otherwise lacked gets put into motion. He learns how to swim, how to cook, and even how to date for her. And while he remains the same man he was before, by the end, he’s exactly what he set out to be: a better version of himself.
When every single character wishes Jack success and happiness in life, it’s hard not to want the same for him. His friends, his boss, strangers, acquaintances, and even his best friend’s enemy all do whatever they can to help Jack succeed. Somehow, this slovenly slug has formed a world around himself which, in every respect, wishes to help him out. However, what’s unclear is how Jack, with this colossal support system, ended up living in his uncle’s basement without ever learning how to swim, cook, or date. Did the world suddenly decide to go easy on Jack just because he meets a nice girl? What’s more probable is that Jack decided to go easy on himself, stepped out of his own way, and allowed himself to finally see the version of Jack that his friends had been seeing all along. The story’s been told before but where Boating really succeeds is in the characters the story is being told about.
Jack has two friends, Clyde and Lucy, a childless couple with a beat up marriage. Jack’s blooming connection with Connie is mirrored by their maturely fucked-up view of relationships. Clyde is also a limo driver whose persistent smile serves a shield for life’s shit. Clyde’s the leader of Jack’s morale boosters. Always willing to sacrifice his own wants and needs for his friend, Clyde does all he can to help his friend. While each performance in Boating is noteworthy, John Ortiz, who plays Clyde, steals the show each time he’s on screen. Ortiz emanates an energy and a likability that shines through his dreary surroundings and situations. Daphne-Rubin Vega holds her own as Lucy, a complex character who tries to prepare Jack for the less glamorous things that relationships will bring.
There are a lot of things to like about Jack Goes Boating. The performances are strong, the depiction of New York City shows a whole different New York than audiences will be used to seeing, and the music (mostly performed by indie rock group Grizzly Bear) holds all of the pieces together. Having performed in Bob Glaudini’s play, which Glaudini later adapted for the screen, Hoffman and his cohorts arrived to the film with a deep understanding of the material. This preparation is visible on-screen. Boating is a well-constructed film with a lot of heart. Its sympathetic characters and commanding performances make up for its worn-out story.
Directed: Philip Seymour Hoffman
Written: Bob Glaudini
Starring: Philip Seymour Hoffman, Amy Ryan, John Ortiz, Daphne Rubin-Vega
U.S.A., 89 min.