Sideways
Originally written for The Milpitas Post
Directed by: Alexander Payne
Starring: Thomas Haden Church, Paul Giamatti, Virginia Madsen, Sandra Oh
Rated: R for language, some strong sexual content and nudity.
Parental Notes: “Sideways” has some brief but fairly graphic sex in it and youngsters probably won’t enjoy the film anyway. Teenagers may enjoy it if they like character studies and intelligent humor.
It’s not often that a movie comes along and presents us with a well made and enjoyable buddy story about two pals who are so deeply flawed that they come close to being actively bad people. “Sideways” gives us Jack (Thomas Haden Church) and Miles (Paul Giamatti), who have been friends since they were roommates back in college. Jack is a has-been actor about to get married and Miles is a divorced, nearly-failed novelist.
Within a few minutes of the opening credits, we see Miles make himself and Jack phenomenally late for their last vacation together as single guys, then steal money from his mother so he’ll be able to show his friend around in style. Jack, on the other hand, is cheerfully crude and, we soon learn, all to eager to have one last fling (or two, or three) before his wedding day. It’s easy to understand and forgive them, though, because the people who suffer most when Jack and Miles mess up are themselves.
“Sideways” isn’t just about their failings. It’s about why their friendship works even though they have almost nothing in common (Miles is a morose intellectual and utter wine geek while Jack is affably pedestrian and will try to sleep with any female within range). It’s also about their approaches to seeking happiness – hence the title, which refers not only to how wine should be stored but also to the way Miles and Jack approach life and relationships.
While up in wine country, the men meet Maya (Virginia Madsen), a waitress at a restaurant where Miles is a regular, and her friend Stephanie (Sandra Oh), a pourer in a wine tasting room who is at least as interested in Jack as he is in her. Miles doesn’t think he has a chance with Maya, and with the help Jack keeps trying to give him, he may never come close to hooking up with her. Jack and Stephanie, meanwhile, are on the same wavelength, except that Jack is soon making relationship noises and still hasn’t mentioned his impending wedding.
Probably the easiest way to sum up “Sideways” is to say that it’s a chick flick for guys. It has all the emotional resonance and romantic humor of a typical movie aimed at women but it’s clearly by, about, and for men. This is a wry look at the ways Jack and Miles sabotage their own – and sometimes each other’s – happiness time and again It’s frequently hysterically funny, and often that humor cuts close to the bone.
Although the ending is ultimately happy (of course) it’s also problematic. Even if we can forgive Jack and Miles for the things they do during the movie, they’re trying to make a clean break with their pasts as they wrap things up, and it’s hard to be convinced that they’ve changed for the long haul. Jack may be promising fidelity but we know he’s driven to sleep around. Miles may have swallowed his fear and reached for happiness, but we also know he’s perfectly capable of making himself miserable regardless of his surroundings. But Jack and Miles are making a leap of faith, and it’s up to us whether we take it with them and choose to believe they can succeed in finding happiness even in their own sideways fashion.