Jack Goes Boating is Philip Seymour Hoffman's movie — it's his directorial debut; he stars as its namesake sad sack; he wears his hair in those terrible dreadlocks that he covered with a big woolen hat at the Oscars last spring — but let's talk about John Ortiz instead. Yes, Hoffman is the famous face of Jack Goes Boating — just as he was at New York's LAByrinth Theater, which he co-directed for many years with Ortiz, making it a downtown incubator for sprawling, poetic drama — but Ortiz, who plays Jack's best friend, Clyde, is the film's urgent, beating heart.
Clyde drives black cars for the same limo company as Jack, and as the grownup of the pair — he's in a long-term relationship with Lucy (Daphne Rubin-Vega) and taking night classes — he has set himself to the task of bettering Jack's life. He finds his friend a girl, prickly mortuary assistant Connie (Amy Ryan); arranges for cooking lessons; teaches him to swim. Ortiz finds in Clyde the Henry Higgins impulse, which has him splashing in a Harlem pool with a guy who's afraid even to put his face in the water. The actor also digs deeper to find the resentment and shame that pushes Clyde toward Jack even as it pulls him away from Lucy.
If it accomplished nothing else, Jack Goes Boating would be worthwhile just as the calling card that gets Ortiz better film roles. Luckily, there's plenty else to appreciate, starting with the movie's three other leads. Connie, as written by Bob Glaudini (who adapted his own LAByrinth play), is a bundle of neuroses and sexual hang-ups, but Ryan makes her recognizable and worthy of Jack's devotion. Rubin-Vega — another theater vet — finds the roots of Lucy's ongoing exasperation with Clyde.
And Hoffman is Hoffman: He's great. His performance, a reprise of the role he played onstage — in fact, each of the principals save Ryan played these roles at the Public — is lived-in and as natural as breathing. Jack is a shy, dreadlocked guy who likes to listen to "Rivers of Babylon" on an honest-to-God cassette Walkman, and who learns, over the course of the movie, that his body is not necessarily his enemy. Visualizing the pool, Jack practices his side-breathing as he walks; imagining himself in the kitchen, he assembles a gratin in the air. Even his first fumbling sexual encounter with Connie turns nervous finger-blasting into unlikely physical poetry.
Hoffman has never been a vain actor, and as a director, he remains uninterested in making himself look good. Early in his career, his self-abasement could feel as punitive to audiences as to the characters he played. But there's no pain in watching him inhabit Jack's unglamorous world, only the fun of seeing a good actor click in a good part he's thought a lot about.
Skirting some of the excess that LAByrinth's artist-friendly environment can foster, Hoffman transfers to film the company's ethos of an ensemble performing with honesty encouragingly well. That's why it's fitting that this drama gets so much from, Ortiz. In the actor's funniest Jack Goes Boating comes to a head at a boozy dinner party that veers into harsh emotional territory. "Let's smoke a toast!" an anxious Clyde shouts, before the party goes astray. Celebrating his best friend Jack's success with a hookah, Clyde is as messy, warm-hearted, and complicated then as this pleasure of a film.