I am not drinking f---ing Merlot!
it might be too much to consider Sideways Payne's masterpiece - in truth he has yet to make a film that isn't at the very least, a minor classic. (Downsizing is the only real exception to that.) But SIdeways is the film where he comes the closest to embracing the level of a genuine comedy. All of his other movies save Election exist in a the world where they could serve as either a bleak comedy or a humorous drama. The Golden Globes has never been comfortable with classifying almost all of his other films in one category or the other, and they seem to alternate with each new one.
Sideways is a wonderful comedy that is not pretentious PRECISELY because both its leads appear to be. Giamatti was already one of the more itnriguing character actors in history but this movie unlocked his potential for the kind of leading man he could be. He has now become one of the greatest and arguably the most underrated actor in history, though television has given him more his due tna the films have. After this film he moved away from the nebbish character to a more different style of leading man and as he has grown older he has gotten better. Incredibly the Oscars denied him a nomination for his work in this film.
Church, whose career was on the downside has been moving in interesting direction since then though he's never had the comic brilliance the same way. Madsen gave one of the great performances of an undervalued career. I don't question the Oscars on either choice that year: both Morgan Freeman in Million Dollar Baby and Cate Blanchett in the Aviator were spectacular. But considering that each of them has gotten multiple bites at the apple since and neither Church nor Madsen ever got another chance, one wonders if they could have waited.
Payne's Oscar for adapted screenplay was deserved though by this point its hard to find a film he's written where he hasn't deserved it. I honestly think he should have more Oscars then he does; with the exception of AARON Sorkin, there is no better screenwriter in Hollywood nor one more awarded. But unlike Sorkin where the dialogue always sparkles, Payne's dialogue is far more built in character and his direction with a crispness that has a melancholy even with its win. No writer has better captured the rituals of life better than Payne, whether through high school in Election, aging in ABout Schmidt, libertine before marriage in Sideways, family among crisis as in the Descendants, or aging and parental relationship in Nebraska. Payne can do no wrong in my eyes because he is a amster craftsman at understanding life and how it only moves in one direction. All of the chaarcters in his movies know this and try to find the bonds they can throughout. They understand life is tragi-comedy and you laugh so you do not cry. In almost every Payne film we do both.