Sideways (2004): Alexamder Payne’s Oscar-Winning Dramedy about Midlife Crisis, Drinking, and Talking, Starring Thomas Hayden Church and Virginia Madseng

A lot of wine floats around in Alexander Payne’s Sideways, a serio-comedy about midlife crisis, in which drinking wine (and talking about it) are not just  routine activities but also represent existential ways of life.


Our Grade: **** out of *****

With the vintage flowing, it will be easy for viewers to succumb to the film’s unique charm and feel a little sideways themselves, just like the story’s two middle-age characters.

Sideways displays more effectively and effortlessly the kind of humanist existentialism that other independent directors have tried for but seldom achieved.

Read about Downsizing (2017): Payne’s Worst Film?

Downsizing: Payne’s Ambitious, Incoherent, Divisive, Disappointing Film

Unlike most directors of his generation, Payne is both a satirist and a humanist. In his early efforts (Citizen Ruth, Election), which were sardonic takes on Midwest mores, Payne adopted a satirist mode in the vein of Preston Sturges, with a touch of Capra but without pathos or sentimentality.

With About Schmidt and now Sideways, however, Payne may be joining thematically (if not stylistically) the company of the greatest humanist of them all, Jean Renoir.  Like Renoir, Payne knows that self-conscious humanism could seem fake, and also like the French auteur, he doesn’t distinguish between good and bad characters. In Payne’s films, all the characters have good, bad, and inconsistent dimensions, and they don’t behave according to a pre-determined scheme.

Clarity and tolerance are the greatest artistic achievements of Payne’s films, whose lyrical beauty grows naturally out of the realization of the inherent sadness and failure in everyday life. Payne’s is a cinema of outsiders, of lost souls. Consider the protagonists of his films: A paint-sniffing working-class woman (Laura Dern) in Citizen Ruth, an overachieving student (Reese Witherspoon) in Election, and a floundering retiree (Jack Nicholson) who finds salvation and redemption in About Schmidt. Payne likes the flawed humanity of his ordinary characters, the strange nature of their egos, their routine rites that somehow take on a sacred meaning. In Schmidt, Payne never made it clear whether this protagonist is a hollow man or a product of attrition of modern life.

Though Sideways is the first film not set or shot in Payne’s native land, Nebraska, the movie is not so much a point of departure as a continued exploration of recurring themes and styles. Whether or not they’re physically set on the road (like About Schmidt), all of Payne’s films are road movies because they depict journeys of self-discovery. Like Schmidt, Sideways is another sad-sack story of highly flawed individuals trying to find meaning in their mundane lives.

In adapting Rex Pickett’s novel (which was unpublished when Payne read it), Payne and his writing partner Jim Taylor have created a tragicomedy about a weeklong existential odyssey through California’s wine country.

Following his triumph as Harvey Pekar in American Splendor, Paul Giamatti gives another stupendous performance as Miles, a struggling novelist and wine-snob who drives to the Santa Ynez Valley for a last-hurrah vacation of bonding and wine tasting with his best friend from school, Jack (Thomas Haden Church), who’s about to be married.

Shooting in California’s vineyards a road movie about the mid-life crisis of two depressed losers might sounds as a bad combination, but it’s actually a winning one, a fertile ground to explore some more serious issues.

As always with Payne, the dialogue is sharp, and amidst the jovial humor, he makes some poignant observations about middle-age, different facets of masculinity (both mature and immature), and the nature of male camaraderie.

The (mis) adventures begin when Miles, a divorce who has not recovered from his failed marriage, decides to gift his old college buddy Jack with a celebratory trip to the Santa Barbara vineyards. The first reel feels like a buddy-buddy picture, with Miles and Jack as a marvelous variation of the Odd Couple. Jack is attractive, charming, and over-sexed; Miles is a sad-sack worrier. Jack is looking for his “last taste of freedom”; Miles is more interested in the perfect wine. Jack would be pleased with cheap Merlot; Miles would not settle on anything less than the perfect Pinot.

However, the audience soon realizes what the couple may only sense subconsciously, that despite differences, deep down, they share more things in common than either is willing to admit. Both Jack and Miles are uniquely American characters, at once products and victims of fading youth and failed ambitions. Once handsome and ambitious, Jack is now an over-the-hill actor who mostly makes TV commercials, whereas Miles still needs to see one of his novels published. It is this thematic element that provides continuity with Payne’s other films, all of which are wry explorations of the American Dream, be it the price and rewards of competition as in Election, or the ruined pastures of old age and loneliness as in Schmidt.

Set over a week period, the film is divided into chapter-days, which gives the story a clear structure and also points to the character’s evolution and change. During this fateful week, Jack falls head-over-heels for a local wine pourer, Stephanie (Sandra Oh, Payne’s wife), and threatens to call off his nuptials. Miles begins his own romantic encounter with an erotic, unpredictable wine-savvy waitress (Virginia Madsen in a sexy comeback performance). All along, both men navigate dangerously through their respective midlife crises, as the women quickly divert the men’s trips and threaten their very futures.

A speech about wine, made by Maya, serves as a metaphor for a whole philosophy of life. She says: “A bottle of wine is actually alive. It’s constantly evolving and gaining complexity, until it peaks and begins its steady, inevitable decline. And it tastes so f—ing good.” At other times, too, when the characters talk about wine, it’s easy to believe they’re talking about something else. Consider, for example, Miles’ speech about Pinot: “It’s a hard grape to grow. It’s thin-skinned, temperamental. It’s not a survivor like Cabernet that can grow anywhere and thrive even when neglected. Pinot needs constant care and attention.”

Sideways is the kind of film in which a debate about the enduring war between Pinot and Cabernet is just as important as the enduring war between the sexes, or the enduring arguments between Miles and Jack about getting laid.

It’s a testament to Payne’s subtle treatment that Sideways succeeds both as a poignant portrait of male friendship and as a love letter to the wine country–while not neglecting the crucial roles that women play in the daily lives of its male protagonists,