Every Philip Seymour Hoffman Movie Ranked Worst To Best

Jack Goes Boating was the only film Philip Seymour Hoffman ever directed. Casting himself as socially awkward limo driver Jack, the film takes a look at one man's attempt to win over his friend's co-worker (Amy Ryan) whilst his friends' (John Ortiz and Daphne Rubin-Vega) marriage slowly implodes.

It's a charming and funny movie that allows Hoffman to play a romantic lead in a relatively typical rom-com, and though it doesn't break any ground from a genre or narrative standpoint, it's still a sweet little film every Hoffman fan should check out.