Sideways (2004)

'Sideways' is brilliant any way you look at it
Miles is the hero of Alexander Payne's "Sideways," which is as lovable a movie as "Fargo," although in a completely different way. He's an English teacher in middle school whose marriage has failed, whose novel seems in the process of failing, whose mother apparently understands that when he visits her, it is because he loves her, and also because he needs to steal some of her money. Miles is not perfect, but the way Paul Giamatti plays him, we forgive him his trespasses, because he trespasses most of all against himself.
Miles' friend Jack is getting married in a week. They would seem to have little in common. Jack is a big, blond, jovial man at the peak of fleshy middle-aged handsomeness, and Miles looks like -- well, if you know who Harvey Pekar is, that's who Giamatti played in his previous movie. But Jack and Miles have been friends since they were college roommates, and their friendship endures because together they add up to a relatively complete person.
Miles, as the best man, wants to take Jack on a weeklong bachelor party in the California wine country, which makes perfect sense, because whatever an alcoholic says he is planning, at the basic level he is planning his drinking. Jack's addiction is to women. "My best man gift to you," he tells Miles, "will be to get you laid."

Some terrible misunderstandings (and even worse understandings) take place, tragedy grows confused with slapstick, and why Miles finds himself creeping through the house of a fat waitress and her alarming husband would be completely implausible if we had not seen it coming every step of the way. Happiness is distributed where needed and withheld where deserved, and at the end of the movie we feel like seeing it again
Paul Giamatti and Thomas Haden Church give the performances of their lives, complemented by two outstanding female leads: Sandra Oh and Virginia Madsen. 
Sideways received  5 Oscar nominations : Best Picture, Best Director (Alexander Payne), Best Adapted Screenplay (Payne and Jim Taylor), Best Supporting Actor (Thomas Haden Church) and Best Supporting Actress (Virginia Madsen). Surprisingly, Paul Giamatti was not nominated for his starring role.
"New classics of American cinema don't come along that often, so grab this one with both hands."