Raise your glasses to a vintage American comedy that gets damn near everything right you can wait around and hope, but you won't have a better time at the movies this year than you will at Sideways. This baby has it all: inspired direction by Alexander Payne (Citizen Ruth, Election, About Schmidt), who fuses bracing wit and emotional gravity into something funny, touching and vital; a nuanced script by Payne and Jim Taylor, from Rex Pickett's novel, that serves as a model of screen adaptation by shaping dialogue into classic comic contours; and a quartet of actors who qualify as a cinematic dream team.
And to what end have these paragons turned their attention? A lowly buddy flick, from a quick glance. Miles (Paul Giamatti), a failed novelist, is taking his best pal, Jack (Thomas Haden Church), a former soap star reduced to doing commercials, on a last fling before Miles serves as best man at Jack's L.A. wedding. Their destination is California's Santa Ynez Valley, where wine-snob Miles hopes to drink himself sideways on the local vino and wine-idiot Jack hopes to get his "bone smooched" by hottie waitresses. Hollywood would love to make that movie. Payne, bless him, would rather die.
Payne crafts human comedies that transcend formula. Sideways is drunk on wine: its allure, its fragility, its vocabulary. Miles has been officially depressed for two years — that's when his wife left him. He is stagnant in his job teaching English, anxious that his novel will never be published and bitter that his wife has remarried and is — yikes! — happy. But not even Xanax and Lexapro can dull his passion for the grape.
Enter two women to stir up the plot. Maya, played by Virginia Madsen (the bombshell from Eighties movies such as The Hot Spot), is a wine-obsessed waitress that Miles can't find the courage to hit on. It's Jack who intercedes. He sets up a date by flirting with Maya's sassy friend Stephanie (the dazzling Sandra Oh), a single mom who pours wine for tourists. Stephanie is Jack's equal in carnal come-ons, but he neglects to tell her about his wedding plans, setting up a killingly funny revenge that is trumped only by a hilarious tour de force of a dinner scene that unites the foursome in moral chaos. The laughs in Sideways are laced with feelings that can sneak up and knock you flat.
The actors work miracles. Oh is a deadpan delight. Church, best known for TV's Wings and Ned and Stacey, is irresistibly appealing as rat-bastard Jack. Church takes his breakthrough movie role and runs with it, nailing Jack's rude charm and quiet desperation. Giamatti, a god among American character actors, has never been better, which is saying something. He's hilarious and heartbreaking. And Madsen is a revelation. The years have made her beauty richer, her grasp of character more subtle and affecting. Note to the Academy: The Oscar for Best Supporting Actress belongs right here. Payne gives Madsen and Giamatti the film's most transfixing moments — not in the novel — in which Miles sees himself as a temperamental pinot noir and Maya praises wine for how it evolves, gains complexity, peaks and "tastes so fucking good." Maya's words also apply nicely to the movie. She blasts Miles for hoarding a '61 Cheval Blanc (one of the greatest Bordeaux) for a special occasion: "I think the day you open a '61 Cheval Blanc, that's the special occasion."
Sideways is inarguably a special occasion. Doubters may hedge about calling it a classic and might insist on checking back in a few years to see how it has aged. Fair enough. But it's not too early to call it pure movie bliss.