Sideways (2004) is like a bottle of fine wine, specifically the prized bottle of 1961 Château Cheval Blanc owned by the movie's protagonist, Miles Raymond (Paul Giamatti), a recently divorced wine connoisseur, discontented high school English teacher, and aspiring author. How is the movie like the bottle of wine? Well, the story—which was adapted from Rex Pickett's same-titled novel about a pair of friends on a week-long getaway to Santa Barbara County, California—restrains itself for quite some time before impulsively popping the figurative cork and allowing the audience to enjoy the contents, just like Miles does his bottle after receiving some disheartening news.

           

The movie's also similar to the bottle in another way: 1961 was the birth year of both Generation X and the movie's auteur, Alexander Payne. In short, the bottle, and Miles' unwillingness to drink it, is a metaphor for his unwillingness (and the unwillingness of other Generation Xers) to live authentically. I previously wrote about this, the sensibilities of Generation X, and their reluctance to sell out, across Payne's movies, but with Sideways, Payne really bottled the grapes of their discontent. For that reason, among others, it's Payne's masterpiece; and now, ten years later, with Generation X firmly into adulthood, the vintage is peaking, so to speak.

The plots of each of his major movies, except for his first, Citizen Ruth (1996)—meaning Election, About Schmidt, Sideways, The Descendents (2011), and Nebraska (2013)—prominently deal with affairs and divorces. And what leads to these affairs and divorces? Discontent, in one form or another. (In Citizen Ruth, conservative father Norm [Kurtwood Smith] is tempted by the younger, pregnant, inhalant-addicted Ruth Stoops [Laura Dern], but never acts on it).

The movie opens economically with Miles sleeping through his morning alarm. He's a depressed, lethargic man who figuratively (and almost literally) sleeps through life. He's bogged down by Xanax and Lexapro, which are then exacerbated with unremitting glasses of wine. (It's noteworthy that two of Payne's other movies, Election [1999] and About Schmidt [2002] open with ticking sounds. Their protagonists, too, have wasted their lives).

 

Miles is late for a week-long getaway with his San Diego State freshman year roommate, Jack (Thomas Hayden Church), a former soap actor and current commercial voice actor. Jack's getting married. To celebrate, the men (each of whom are suffering through a mid-life crisis) take a road trip to wine country, where Miles, a wine connoisseur (and downright snob), schools Jack on wine tasting. While Jack, who has an affair with a local winery worker, Stephanie (Sandra Oh), schools Miles on getting laid by Maya (Virginia Madsen), a recently divorced barmaid and old friend of Miles. 

 

Miles is recently divorced, too, having cheated on his ex-wife. In fact, extramarital affairs like Jack's and Miles's, and divorces like Miles's and Maya's, are defining characteristics of both Generation X and Payne's oeuvre.

 

In this way, Sideways is about the production of Sideways: Miles struggles to publish his book reflects the struggles of disenfranchised, independent filmmakers of Generation X, like Payne. What's more, several years before, reality had previously imitated art when nobody would publish Pickett's novel. After more than 100 rejections, it took the success of Payne's adaptation of About Schmidt for St. Martin's to finally purchase the novel—which Payne had previously optioned—for a mere $5,000: an investment which paid off.

           

In 2004, Sideways went from an independent underdog to a critical darling, winning 129 major awards from 178 nominations, including seven Golden Globe nominations (with two wins, including Best Picture – Comedy or Musical) and six Academy Award nominations, including Best Motion Picture of the Year, and a win for Best Writing, Adapted Screenplay.

           

Now, ten years later, Sideways holds a high place as one of the greatest American movies of the 2000s. Personally, I came to the movie—which is among my top ten favorites of all time—after watching The Descendents in 2011 and, admiring Payne's impressive balance of comedy and drama, sought his other works, including Sideways, and, eventually, the man himself at the 2013 Savannah Film Festival.

           

I've now seen the movie five or six times. Each time, I have new, rich observations. For instance, this time around, I caught the subtle inclusion of Eddie Money's "Two Tickets to Paradise”, which plays in the background as Miles and Jack talk at a bar: a rich addition—whose title plays on the duo's trip—about waiting and finally taking action. I also noticed that at the Windmill, where Miles and Jack stay in Santa Barbara County, Miles casually watches John Ford's adaptation of The Grapes of Wrath (1940): another rich addition to Sideways, considering the titular pun (grapes/wine), how each movie's about discontented Americans road-tripping through California in search of contentment, and how each of those Americans end up more discontented than when they begun the journey.

           

Surely, Generation X can appreciate the artistry, skill, subtlety, and metaphorical weight that Sideways conveys this discontent with. For them, as they pass through adulthood, the vintage is peaking, and should continue to peak for some time. But for how long? Personally, as a Millennial who relates to Sideways in other, more individualistic ways, I hope that the vintage holds and becomes an old classic, somewhere on the same vine as The Grapes of Wrath; that level of esteem. I hope that, in another ten years, Sideways will prove timeless, its observations, universal. 

 

by Scotty Barnhart