Akin to 2009’s Adam, Jack Goes Boating is a film that evokes typical indie filmmaking tropes while attempting to make broad statements with its limited reach. The film, adapted from a stageplay that Hoffman had previously starred in, never escapes its stage roots. Its central locale, an apartment, is a confining space that houses more awkward drama than it can stand. Jack Goes Boating does provide both Hoffman and co-star Amy Ryan with a sweet, sometimes sincere, acting showcase, but supporting actors John Ortiz and Daphne Rubin-Vega are clearly incapable of matching the leads presence and personality. The gap between actors is glaringly obvious, and quite distracting.
Hoffman’s direction is adequate, if unremarkable. Moments that are meant to establish a contrast between illusion and reality provide for nifty, if not gimmicky, camera tricks, though nothing here really exudes of a directorial presence or signature. I would attribute this largely to the confining nature of the screenplay, which is just so plain and ordinary. Quite honestly, if it had not been for the lead characters chewing the scenery, the whole thing could’ve collapsed unto itself.