Jack Goes Boating (2010)

Comedy, Drama, Romance

Director: Philip Seymour Hoffman
Writer: Robert Glaudini
Starring: Philip Seymour Hoffman, John Ortiz, Richard Petrocelli, Thomas McCarthy

"In love you either sink or swim."

The directorial debut of actor Philip Seymour Hoffman and the only film he's ever directed is an underseen feel-good romantic-comedy-drama that's definitely worth a watch.

Jack (Hoffman) is a middle-aged  single New York City limo driver who likes reggae music for its positivity. One day, his best friend Clyde sets him up with Connie (Amy Ryan), his wife Lucy's new coworker. As the two slowly grow on each other, Connie inspiring Jack to improve himself – he learns to swim and cook to impress her – their mutual friends Clyde and Lucy's relationship threatens to collapse from betrayal and jealousy and each couple comes face to face with the inevitable path of their relationship.

Made as the screen version of a play by the same name and starring the same cast (except Ryan), with amazing acting from the cast, especially from lead Hoffman, who, as usual, never ceases to amaze with his performances, Jack Goes Boating is a pretty touching story about how love can be (often at the same time) awkward, funny, and important.

Plot summary from IMDb: Jack is a shy and awkward man who drives a limo and lives an unassuming life. His friend and co-worker, Clyde, and his wife Lucy, feel sorry for Jack and set him up on a blind date with Connie. Connie shares Jack's shyness and awkwardness, but through each other they seem to be able to find solace within themselves. Trouble might be brewing in paradise though, as Clyde and Lucy's marriage stumbles just as Jack and Connie's relationship grows.

Awards: 1 win & 7 nominations.
Runtime: 89 min
R