Alexander Payne’s SIDEWAYS is one of the great American comedies of the 2000s, and one of the rare films that manages to be funny, sad, embarrassing, romantic, and quietly devastating all at once. On paper it is a road movie about two middle-aged friends heading into wine country before one of them gets married. In practice it becomes a study of male failure, self-delusion, longing, and the strange things people reveal about themselves when they are trying to impress somebody else.
Paul Giamatti gives one of the best performances of his career as a man whose intelligence only makes his disappointment in life feel sharper. Around him the film keeps finding moments of humiliation, tenderness, and comic disaster without ever pushing too hard. It is warm, literate, and deeply rewatchable.