Miles Raymond isn't much of a catch. He is short, dumpy, divorced, past 40 and teaches junior-high English while toiling on a novel that no one seems eager to publish. "My life is half over and I have nothing to show for it," Miles (Giamatti) wails in self-pity. F. Scott Fitzgerald long ago claimed that there are no second acts in American lives, but in this wonderfully humanist film, Miles clearly lays the groundwork for his.
Sideways is another banner effort from director-cowriter Alexander Payne, 43, whose earlier movies include Election and About Schmidt. Payne just may be the single most talented director of his generation. Like his other films, Sideways is bittersweet, full of humor that's alternately gentle and raucous (a rampaging-naked-guy scene is a hoot) and completely accepting of its characters as it reveals their strengths and weaknesses. Miles, an oenophile, heads out on a weeklong trip with Jack (Church), a college pal, to California's wine country. Jack is about to marry and, as he puts it, "this is our week to get crazy." Both men do exactly that, in their own ways, especially after taking up with two women—Miles with a waitress (Madsen) and Jack with a single mother (Oh)—in a town they are visiting.
The cast is superb. No one plays smart sad sacks better than Giamatti. Church perfectly nails Jack's swagger and secret sweats, and Oh delivers another small gem of a comic performance. The surprise here, and hallelujah for it, is the warm, expert turn by '80s starlet Madsen as a mature woman who isn't falling for any man's line. Sideways is one of those rare movies filled with characters so vivid that when the closing credits roll, you're almost disappointed because you so want to keep watching these folks as their lives unfold. (R)