Sideways (2004)

Movie Info

Movie Info


VP Content Ratings

Sex & Nudity
Rated R. Our ratings: V-1; L-5; S-5/N-5

Happy are those to whom the LORD imputes no iniquity, and in whose spirit there is no deceit.
Psalm 32:2

I said to myself, “Come now, I will make a test of pleasure; enjoy yourself.” But again, this also was vanity. I said of laughter, “It is mad,” and of pleasure, “What use is it?” I searched with my mind how to cheer my body with wine—my mind still guiding me with wisdom—and how to lay hold on folly, until I might see what was good for mortals to do under heaven during the few days of their life. I made great works; I built houses and planted vineyards for myself… and again, all was vanity and a chasing after wind, and there was nothing to be gained under the sun.
Ecclesiastes 2:1-4, 11b


Director Alexander Payne, whose perceptive films Election and About Schmidt combined comedy and drama to explore serious themes, teams up again with writer Jim Taylor (About Schmidt) to produce one of the most effective and moving films of the year based on the novel by Rex Pickett. Miles Faymond (Paul Giamatti), still smoldering over his two year-old divorce, is late as usual in picking up his old college roommate Jack (Thomas Haden Church). He wants to take his buddy on one last fling before the latter marries at the end of the week. The two are like Felix and Oscar of “The Odd Couple.” Miles, a middle school teacher and would-be novelist, is neat and tidy, and possesses an almost obsessive knowledge of wine and grapes. Jack, sloppy and happy go luck, is an actor best known for one soap opera role and voice-overs for TV commercials: he possesses an almost equally obsessive desire to sample all the favors he can from women before he settles down. Thus Miles intends their five days touring the Santa Ynez Valley to be a time of sampling fine wines, playing golf, and strengthening the ties that have bound them together despite their great differences. However, not long after they drive away from his in-laws, Jack declares that his goal for the trip is “to get laid.”

At each winery stop Miles meticulously describes the flavors of the sample, its year of vintage, and the history of the grapes from which it came. Jack sometimes asks when he can taste it, and then sipping from his glass, nods his head as if in complete (and understanding) agreement. After checking into the motel that will be their base, the two walk to Miles’ favorite restaurant in the area, where they are waited upon by Maya (Virginia Madsen), whom Miles has met before. Jack immediately wants to hook up the two, even telling Maya that Miles’ novel is about to be published. The would-be author, knowing that it is just being considered by a small press, is embarrassed by this, but does not correct his friend’s story—nor does he pursue Maya, even though they learn she has been divorced.

The next day whereas Miles is focused on the wine samples, Jack zeroes in on the server, the lovely Stephanie (Sandra Oh), who soon reciprocates Jack’s passion. It turns out she is a friend of Maya, and so that night they pair up at Stephanie’s house. Neither of the men mention Jack’s upcoming marriage. Jack and Stephanie heatedly make out in one room, whereas Miles and Maya talk, the two discovering that they share a mutual love for fine wines. Miles has finally found someone, other than his ex-wife who also was a wine connoisseur, who shares his knowledge and passion for wine and grapes. Their conversation reveals much about each person. Maya is obviously drawn to Miles, but he is still too upset by the news of his ex-wife’s remarriage that he has just received that day to be able to act on his own attraction to her. But, when they part, Maya agrees to take a copy of the manuscript of his novel and read it—an act that will prove to be very important later on, and a re-invigorating means of grace.

During the following few days Miles continues to engage in sex with Stephanie as if there were no wedding coming up at the end of the week. He leaves his buddy, disappointed and alone most of the time, even taking over their motel room during one of his and Stephanie’s trysts. The despondent Miles—even more so than usual because his agent tells him that the publishers have passed on his novel—angry and feeling that his life amounts to nothing, gets into some amusing (to us) trouble at a winery when he samples far too much. Then, when he finally gets back with Maya and inadvertently reveals that Jack is about to get married, his and Jack’s affairs come to a crashing halt. And I do mean “crashing,” in that an angry Stephanie bashes Jack’s face with her heavy handbag, so much that Miles has to take him to the hospital for stitches and the setting of his broken nose. It would seem that, as the two return to southern California, the past few days are over and done with, Maya being furiousthat Miles had not told her the truth about Jack earlier.

The film opens and closes with a knock on the door. The first one, summoning the oversleeping Miles to move his car, might represent his past and present mistakes. The second is the result of an act of grace, and represents a far more hopeful future. The four lead actors perfectly embody their roles, with Paul Giamatti at last getting the break-through role he so deserves. The film is beautifully photographed, and the sequence of split screens (sometimes as many as six and more) showing the two men, the wines and their succulent grapes, is very effective in conveying the fullness of their day spent going to so many wineries. You will hardly ever see a more sophisticated film about the joys and pains of romantic relationships, punctuated by several moments of grace, as this one!

For Reflection/Discussion

1) Where does the pair make their first stop? What does this reveal about Miles? Also, their staying with his mother far longer than they had intended? What darker side do we see of Miles when he sneaks upstairs during supper?

2) Compare the two men. What interests each the most? How do we see that Miles is still living more in the past? What can he not let go?

3) What does Miles telling Maya why he favors so much Pinot Noir and its grapes reveal about his character? And her description of her favorite wine reveal about her?

4) What do you think the story is saying about the result of deception? How does it hurt everyone involved? Do you think Jack has learned anything from his experience? What do you think are chances that his marriage will succeed? From the scene following the wedding ceremony, do you think that Miles has grown in maturity? In what way?

5) Koholeth in Ecclesiastes speaks of vanity and fools. Where in the film do you see the two characters as fools? Do you think either one achieves the wisdom described in the biblical book?

6) Where do you see moments of grace in the film, one of them being very funny and risky? How does grace finally encompass Miles’ life?

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