Phillip Seymour Hoffman (Doubt, Capote) is one of America's best actors, and now he's trying his hand at directing. Amy Ryan (Gone Baby Gone and TV's The Office) is also exceedingly talented and adorable. Unfortunately, Jack Goes Boating isn't as good as the sum of its parts.

 

The story is a dark one - working class folks in New York City looking for love - and these characters all have more than their fair share of personal issues. Hoffman's married friends (John Ortiz and Daphne Rubin-Vega) set him up with Ryan, and their double-date is awkward to say the least. And it doesn't help that the married friends are having lots and lots of troubles in their own relationship. These four characters' jobs suck, their apartments suck, it's freezing cold in the Big Apple, and a layer of filth seems to cover everything in this movie. If you know someone who's desperate to move to NYC and you'd rather they didn't, just show them this film and I bet they stay where they are.

 

If you're going to ask me to watch sad people lead sad, lonely lives in a sad story for an hour and a half, I have to be able to connect to at least a couple of the characters, and I just couldn't with this film. Having said that, this film proves once again what an amazing talent we have in Phillip Seymour Hoffman, and I'm looking forward to seeing him in something else, anything else, very soon!