Directed by Alexander Payne
This is a favorite of mine and one that I have been looking forward to for a long time. I find the character of Miles extremely relatable (probably not a good thing) and the dialogue in this film absolutely brilliant.
Miles is taking is old college roommate Jack on a wine tour to celebrate Jack's upcoming nuptials. Miles is failed divorced author whose wine obsession is clearly more than just a hobby, while Jack is a washed up actor. Much to Miles' dismay, Jack informs him that he plans on getting laid on the trip and will do everything he can to make sure Miles has sex too. Jack finds what he is looking for in a sexy wine pourer and Miles becomes interested in her friend Maya.
In lesser hands, this would have been a fairly disgusting bromance movie, where the two leads form an unlikely bond while having gross sexual misadventures. Fortunately, Payne never condescends to the viewer and delivers a very real story about two flawed friends. No one plays a down and out loser better than Paul Giamatti. The scene between Maya and Miles when they discuss their love of wine is truly beautiful and always makes me feel guilty that I avoid red wine completely. The humor in this film comes from very genuine human foibles and awkwardness, which is something we can all relate to. If this were a typical Hollywood comedy, there probably would have been some misunderstanding involving a prostitute.
Another strong contender for the Best Picture Oscar of the 00s (one of the most coveted awards in recent history).
The food that Miles, Jack, and Miles' mother ate together gave all of the actors food poisoning.
Most of the wine the actors' drank was non alcoholic.
Paul Giamatti doesn't like wine.