The feature film directorial debut of Philip Seymour Hoffman, Jack
Goes Boating is a characteristically morose wallow in indie-style
shoe-gazing that should only please the most dedicated fans of the
talented actor, along with devotees of somewhat similar sad-sack works like Todd Solondz’s
Happiness and James Mangold’s Heavy.

Hoffman stars as oafish limo driver Jack, who masks his sadness with the good-vibe positivity of reggae music, which he keeps in constant rotation on his Walkman. (Yes, Walkman — take that, Steve Jobs!) At the urging of his (only) friend and coworker, Clyde (John Ortiz), Jack awkwardly, elliptically pursues another brokenhearted New Yorker, Connie (Amy Ryan), learning to cook for her since she claims she’s never had anyone fix her a meal. Booze and weed come out, and lingering resentments between Clyde and his wife Lucy (Daphne Rubin-Vega) eventually come bubbling to the surface at an awkward dinner party.

Jack Goes Boating is adapted by Bob Glaudini from his own stageplay (which Hoffman and Ortiz, old theater chums, each have a history with), but the material lacks enough emotional punch to connect as either a more realistically rooted portrait of wounded-soul adult love, or enough sharp-tack detail to score as a searing musing on life’s accumulated miseries. To make up for relatively meager dramatic stakes and goose up the affected melancholy, Hoffman slathers on a jazz score and throws in some montages, to little lasting effect. “Everybody hurts,” R.E.M. once opined. True, but not all portraits of wallflower pain are created equal. (Overture, R, 89 minutes)