Sideways is not a perfect film. There are some contrivances of character and plot, and director Alexander Payne is hardly a visual pioneer. But the movie’s personal appeal and the pathos of its protagonist give this wine-tour buddy comedy a full body and lots of subtle overtones.
Sidekick Reversed

TV wine commercial photography: style, wink, or accident?
Miles and Jack (Paul Giamatti and Thomas Haden Church) are pals, although if they hadn’t met in college, they probably wouldn’t have sought each other’s company. Jack is an actor, his deep voice and sun-kissed good looks augmenting his outgoing, confident persona.
Miles is much less of a leading man. He’s a critic and a know-it-all (when it comes to wine). He’s not quite pudgy, but he is a sort of shapeless blob. He works as an English teacher to support his life’s work — writing novels. He’s a little whiny (with an ‘h’) about his lack of success. You might think he’s a lovable loser, but then he steals money from his mother’s underwear drawer, so he’s not even that. And as played by Giamatti, he lacks the commanding presence, the charisma, that most protagonists have.
As his bachelor-party gift to Jack, Miles drives them on a tour through California wine country. Jack wants them both to get laid — himself as a last fling before marriage, and Miles as an overdue rebound from his divorce two years ago. They find two eligible women at different stops — Stephanie (Sandra Oh) is the adventurous match for Jack, and Maya (Virginia Madsen) is the oenophile whose nose and palate just might be a match for Miles’.
Craft vs. Art
There are some contrivances in Sideways that keep it from feeling truly genuine. First of all, the friendship of Miles and Jack seems pretty unlikely. The two are so different that it’s hard to imagine them remaining friends for 20 years. There is also a wacky development that conveniently breaks up the drama and leads to the ending, but feels outside of everyday plausibility.
And even though this is Payne’s fourth feature, it sometimes feels like he’s still learning the trade. Some of the cinematography looks like a golden ’70s TV commercial for Ernest and Julio Gallo, but not all of it. He pans away from the apartment door as the couple go inside after their date, then pans back the next morning. It’s a trick we’ve seen before, even in parodies, but Payne includes it without indicating whether it’s genuine or a wink. The movie just doesn’t seem very sophisticated, not the work of a visual pioneer, but of a journeyman.
Wine Is Life
Nevertheless, the film works. At times it works beautifully.
There is a scene of a commercial winery; the establishing shot shows a fire hose spilling a red into a tanker truck. This winery makes money by selling shirts and hats and an “experience,” instead of appealing to the individual palate. (Their wine is terrible, says Miles.) It is here that Miles gets yet another rejection from a publishing house. We don’t actually know whether Miles’ book is any good, but his publicist tells him it fails because it can’t be easily marketed.
If Miles gets any vindication, it’s that his novel is read by a single person. “The world doesn’t care what I have to say,” he complains, and Sideways is real enough that his complaint is probably true. But Miles can find a silver lining in touching that single person.
The metaphor extends to Sideways itself. Payne has made an unconventional movie where the sidekick is the hero and vice-versa. And although the marketing team has pegged the film as a wine-country buddy-comedy road movie, its real appeal is more subtle and personal.
As Good As It Gets
Perhaps the best thing in Sideways is a single scene. It’s a scene of such heartbreaking power that I’d probably have to recommend the movie simply because it’s included. It’s a short scene, maybe 15 seconds long. It’s not visually beautiful, but it is poetic and pathetic.
I won’t say which scene it is. You’ll recognize it when you see it. It says, in short, that this is as good as it gets. These are the golden days, and they’re not that golden. But it’s all downhill from here, so enjoy today, even if you don’t enjoy it that much.
Sometimes just a sip can convey a dozen different tastes and smells.
Of course this scene doesn’t exist in a vacuum, and Giamatti and Payne earn its power through the duration of the film. They create a protagonist whose aspirations outpace his talents, yet who retains a shred of dignity and humanity through some very small victories. Sideways is a humbling reminder we can’t all be played by Brad Pitt. In our life stories, more of us would be played by Paul Giamatti.