Jack Goes Boating (2010)

Philip Seymour Hoffman is Jack, an awkward fellow whose buddies Daphne Rubin-Vega and John Ortiz set him up with the amazing Amy Ryan in Jack Goes Boating (2010). Amy is more than a little awkward herself, so the pair hit it off nicely. Writer Robert Glaudini adapted the script from his 2007 play, which also starred Phil, Daphne and John. Slow but satisfying, Jack Goes Boating doesn't showboat, but it builds to a nice boil. Plus Daphne in her bra will have you jacking and master-boating all night!