Jack Goes Boating is Philip Seymour Hoffman's movie — his directorial debut. And he stars as its namesake sad sack, wearing his hair in those terrible dreadlocks that he covered with a big woolen hat at the Academy Awards.
But let's talk about John Ortiz instead. Ortiz plays Jack's best friend, Clyde, and is the film's urgent, beating heart. Clyde drives for the same limo company as Jack. And as the grown-up of the pair — he's in a long-term relationship with Lucy (Daphne Rubin-Vega) and taking night classes — he has set himself to bettering Jack's life. He finds Jack a girl, prickly mortuary assistant Connie (Amy Ryan), arranges for cooking lessons, teaches him to swim.
If it accomplishes nothing else, Jack is 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 play), is a bundle of neuroses, but Ryan makes her recognizable and worthy of Jack's devotion. Rubin-Vega finds the roots of Lucy's ongoing exasperation with Clyde. And Hoffman is Hoffman, meaning he's great.