Jack (Thomas Haden Church), an actor whose "star" peaked some eleven years earlier and who now ekes out a living primarily doing commercials, is about to be married. With one week to go before the big day, his best man/friend/former college roommate, Miles (Paul Giamatti), has cooked up a trip to California's wine country, where he proposes a week of friendship, good wine, good food and golf as a send-off for Jack into that most blessed state of matrimony.
As is often the case with the hand that Life deals us, however, the week does not quite go as planned, for a couple of reasons: First, though Miles proclaims this week to be about Jack, Miles is battling his own demons of depression, which have plagued him for going on two years now, ever since his divorce from his beloved Victoria (Jessica Hecht). In addition to which, although he makes his living as an Eighth-Grade English Teacher, Miles is also an aspiring novelist, who happens to be waiting for a call from his agent, who has a publisher interested in the novel Miles has been working on for more than three years. So there is an ulterior motive for Miles at work here; a wine connoisseur, he's taking Jack into country that is not only familiar to him, but is without question a "comfort zone" for Miles, who desperately needs a temporary respite from his own cares right now.
The other problem is that Jack has an inflated ego and an overactive libido, a potent combination that quickly dictates an alternate plan of action for the week. Jack, it seems, is bent on sowing every last wild oat that remains, active or dormant, within him, before his impending nuptials scheduled for the following Saturday. Soon he is involved with Stephanie (Sandra Oh), who works pouring samples of wine for visitors at one of the first vineyards to which Miles takes Jack on their tour.
Jack then successfully devises a plan that gets Miles involved with Maya (Virginia Madsen), a waitress at one of the restaurants Miles frequents on his visits to this part of the world. Maya also happens to be a recent divorcée who is working on her Master's in Horticulture at one of the local colleges, as well as being a wine connoisseur in her own right and a friend of Stephanie's to boot. All of which sounds like the makings of a good time for all, with one exception: Jack conveniently fails to tell Stephanie that he is about to be married.
Bad move, Jack...
In "Sideways," Payne has created a highly entertaining and emotionally involving film with characters and situations to which a broad cross-section of viewers will readily be able to relate and identify. Payne has an eye for nuance and subtlety, which makes his film- essentially a character study- a succinct examination of the human condition.
Subtlety and nuance is exactly what Paul Giamatti brings to the role of Miles, as well. It's a performance that is so real it's almost excruciatingly so at times, but it makes Miles someone you can empathize with. Giamatti creates a sympathetic character you can't help but root for on this vast wilderness of a stage we call life; it's a performance that should easily have earned him an Oscar for Best Actor.
Haden Church does an exemplary job, too, as Jack. He imbues his character with such believable self-centered shallowness that you want to laugh at him and hit him at the same time. The rub is, Jack knows what he's doing, but simply can't help himself; so in the end you may find yourself sympathizing with him anyway, because Haden Church presents Jack as someone who just does not possess the intellectual capacity to do otherwise, which somehow makes you want to let him off the hook. You realize that this is just Jack honestly being who he is. And it takes a good performance to get you as a viewer to that place.
The striking Virginia Madsen does a good job, as well, as Maya, creating a character that is a perfect counterpart to the Miles created by Giamatti. And Sandra Oh, currently riding a surging wave of popularity due to her role on televisions "Grey's Anatomy," brings some definite pizazz to her role of Stephanie, successfully displaying her character's spirit, while at the same time exposing a decidedly vulnerable side of her.
The supporting cast includes Missy Doty (Cammi), M.C. Gainey (Cammi's husband), Patrick Gallagher (Gary the bartender), Marylouise Burke (Mile's mother), Alysia Reiner (Christine) and Stephanie Faracy (Stephanie's mother).
A film that lends itself to repeated viewings, "Sideways" is one of those gems that makes you appreciate not only the artists involved, as well as the art of film-making, but the medium itself. I like this movie more every time I see it.