Sideways is a pretty, poignant, genial tale of two longtime college buddies who embark on a week long tour of wineries and golfing before one of them (Thomas Haden Church) succumbs to the shackles of marriage.
Whatever your taste in buddy movies is, you'll probably find something you like in Sideways, which mixes the effete elitism of wine-lovers with the frat-boy antics of philanderers in wickedly seamless fashion.
Miles (Paul Giamatti) wants to give Jack (Church) a good send off before he joins his betrothed in holy matrimony at the end of the week. Miles, an avid - some would say sneeringly snotty - oenophile, comes up with the nifty idea of the two of them driving up the coast of California touring various wineries and vineyards and such. That way Miles can show off his knowledge and Jack can have a one last good, free time.
One small problem. Although Miles is perfectly content to wine and whine for the week, Jack's eye wanders - and soon he's setting up a double dinner date with a winery employee (Sandra Oh) and a waitress (Virginia Madsen). Suddenly the trip's not about the two friends bonding one last time, it's more about Jack sowing his wild oats (figuratively, hopefully) while he still can. This change in plans leads to awkward, funny, and funny-awkward moments; meanwhile, poor Miles - recovering from a divorce (and finding out secondhand that his ex-wife has just remarried) and waiting to hear if his latest literary opus will be accepted for publication - is a walking rubber band ball of neuroses and nerves. He tries to maintain the trip's focus, while Jack just tries to have a little fun.
As with most buddy films, Things That Go Wrong tend to snowball into something far greater, and on one level Sideways is a typical road trip movie, including assumptions, lies, illogical decisions, red herrings, and so forth - all in the name of low comedy. But on another level, the movie is an honest look at love and relationships from the perspective of a single, closing-in-on-middle-age male.
Even though Giamatti and Church were hardly unknown actors before Sideways, this is truly the breakthrough film for each. Giamatti, a veteran character actor perhaps best known for his role as Pig Vomit in the screen version of Howard Stern's Private Parts, is perfectly in his element as the self-obsessed, nervous, sincere Miles. It's a performance to which many people can instantly relate; Miles is not handsome, he's not smooth, he's not really all that charming, but somehow he's still appealing. He's a good guy who tries to do well and sometimes suffers the whims of Lady Luck. Church is known for two TV series he was in, "Wings" and "Ned & Stacey," and I can't recall his ever being classified as a good actor, just an entertaining one. But he's wonderful as the rowdy, randy, perpetually horny Jack; he seems to give the role an extra layer of depth. You can't just write Jack off as a selfish bastard, just as you can't just write Miles off as a dork.
Director Alexander Payne, who made the clever Election, does a fantastic job at transforming what's really a two-character study (everyone else, including the two female leads, is background to the relationship between Miles and Jack) into a realistic, fully textured movie. Payne's screenplay doesn't dwell on caricatures and doesn't offer pat explanations or resolutions. Sometimes, the film tells us, things don't end up good or bad. They just continue on.
Although Giamatti and Church are at center stage, Oh and Madsen are both fantastic, although perhaps slightly underused. In particular, Madsen (who earned an Oscar nomination, as did Church), makes the most of her brief screen time, oozing intelligence, wit, charm, and sexuality from every pore.
Sideways doesn't move too slowly and isn't too talky, and because wine is one theme, there are plenty of beautifully photographed scenes of the lovely Napa Valley's vineyards. Sideways is thoughtful, entertaining, and fascinating.
