A limo driver falls for his blind date and tries to impress her,
while his best friend's marriage begins to implode due to betrayal.
Jack Goes Boating (2010)
Directed by Philip Seymour Hoffman
Written by Robert Glaudini
Starring Philip Seymour Hoffman, Amy Ryan, John Ortiz,
Based on the stage play by Robert Glaudini
Jack Goes Boating was the only movie that Philip Seymour Hoffman would direct in his career, due to his sudden death in 2014. I like to think he would've gone on to direct more indie films and develop a signature style behind the camera. This film, which I could tell right away was based on a play, is a great depiction of the magic of new love and the pain of dying love. As usual, Hoffman delivers a flawless performance and his chemistry with Amy Ryan is fantastic. I believe their budding relationship, and they're both neurotic as hell and perfect for each other.
Jack is a limo driver trying to better himself. He lives alone and his best friend Clyde (Ortiz) looks out for him, but he struggles with his own shit, just like all of us. Jack gets set up on a blind date with Connie (Ryan), a friend of Clyde's wife Lucy (Rubin-Vega). The two hit it off, and suddenly the development of Jack and Connie's relationship starts to mirror the sharp decline of Clyde and Lucy's. This all culminates in a brutally awkward dinner party scene that showcases all four actors' great talents.
This movie got majorly overlooked and really fell off the radar hard and fast back in 2010. It's a brutal, realistic story of love, betrayal, and friendship that has an honest screenplay and a charming, indie soundtrack. In fact, the whole film has this "good vibes" thing going on that really keeps the audience in an optimistic mindset, even when things are going rough. Not a lot of films can do that.