Sideways (Movie 2004): Alexander Payne’s Overeager Crowd Pleaser

Sideways movie with Paul Giamatti and Thomas Haden Church: Days of Wine and Losers in Alexander Payne’s Southern California Wine Country-set road movie about two middle-aged men-babies who learn life’s lessons while boozing up and making love.

Sideways (movie 2004) review: Alexander Payne’s Southern California Wine Country tour follows conventional path to male maturity

With the 1999 Matthew Broderick-Reese Witherspoon star vehicle Election, Alexander Payne demonstrated a flair for satirical comedy the likes of which would have turned Billy Wilder arugula-green (with envy). With the 2002 Jack Nicholson star vehicle About Schmidt, Payne demonstrated that his comedy flair could go the way of Wilder’s in fluff like Sabrina and Love in the Afternoon: Bland, cutesy, phony. In Sideways, the filmmaker has opted for the latter route.

Payne’s choice is understandable. After all, it helps to explain his film’s popularity with U.S. critics and audiences alike. Except, that is, with those who will find his and Jim Taylor’s adaptation of Rex Pickett’s novel to be an overlong, moralistic, and unabashedly dishonest effort. And unfunny, to boot.

Middle-aged male babies

A road movie about two middle-aged men on the difficult path to maturity, Sideways is problematic at its very core, i.e., the two lead characters – who should have been killed at birth – and the trip itself.

The movie begins with divorced high-school teacher, writer-wannabe, and wine connoisseur Miles (Paul Giamatti) and former TV soap star turned TV commercial announcer Jack (Thomas Haden Church) going on a road trip from San Diego to Southern California’s Wine Country.

The duo’s wine-guzzling excursion is supposed to be Jack’s farewell to his much cherished bachelorhood, which will be over the following Saturday; that’s when he’ll be tying the knot with the wealthy Christine (Alysia Reiner).

While visiting the bars and wineries of the Santa Ynez Valley, they run into two local women, Maya (Virginia Madsen) and Stephanie (Sandra Oh, Alexander Payne’s real-life wife).

A fellow wine connoisseur, Maya bonds with Miles, still depressed over the fact that, after dumping him, his ex-wife has gotten married to someone else (shades of Woody Allen’s Manhattan, minus the lesbianism). One-track-minded Jack, however, is anything but despondent. He bonds with Stephanie on a physical level, tuning out the fact that his marriage is only a few days away.

Lies and betrayals lead to inevitable confessions that lead to angry outbursts that lead to contrived self-examinations that lead to preposterous promises of reconciliation.

Crowd-pleasing beating

Throughout all that drinking, sexing, and moralizing, Thomas Haden Church at least manages to make his tanned, stupid, egocentric, and perennially horny actor (is there any other kind in movies?) a borderline tolerable cliché.

In fact, when Jack gets a broken nose – courtesy of Sandra Oh’s irate Stephanie – one could almost feel sorry for him. But no tears should be shed for Stephanie, as this thirty-something woman should have known better than to think that two days of wild sex were to be taken as a pledge of life-long commitment.

It should be noted that the assault scene is played for laughs. Now, imagine how funny-haha that bit would have been had the situation been reversed, with Jack as the “betrayed” party punching the deceitful Stephanie on the nose.

Sideways movie with Virginia Madsen and Paul Giamatti: Winner of five Los Angeles and four New York film critics awards, plus two National Board of Review and three National Society of Film Critics awards, two Golden Globes, the Best Adapted Screenplay BAFTA, and the Best Cast SAG Award.

The dangers of self-parody

Later on, Jack, more or less looking like the bandaged Jack Nicholson in Chinatown, has his climactic emotional moment: That’s when the middle-aged man realizes what a boy he has been.

Alexander Payne and Jim Taylor’s screenplay provides no assistance to the actor. To the contrary; Jack’s epiphany feels wholly out of character. On the positive side, even though Church is way out of his range, he earns points for avoiding the pitfalls of self-parody.

And to think that following Jack’s tearful breakdown, we’re supposed to believe that his life will be nothing without his future wife. Never mind that everything we’ve seen until then proves the exact opposite.

The dangers of flowery dialogue

Wallowing in self-pity, Paul Giamatti is Sideways’ straight man, failing miserably in his strenuous efforts to make Miles worthy of sympathy. Instead, the morose character comes across as an insufferable bore, at one point ruining the film’s comic climax, when Miles’ devotion to his psychologically stunted actor friend almost results in him getting the beating of his life.

Now, in all fairness to Giamatti, Payne’s direction and his and Taylor’s widely admired, award-winning screenplay are equally to blame.

Here’s Miles, expressing his innermost thoughts in one endless monologue, not found in Rex Pickett’s novel:

Virginia Madsen’s Maya: “Why are you so into Pinot? I mean, it’s like a thing with you.”

Miles: “I don’t know. It’s a hard grape to grow. As you know, right? It’s thin-skinned, temperamental, ripens early. It’s not a survivor like Cabernet that can grow anywhere and thrive even when it’s neglected.

“Pinot needs constant care and attention. In fact, it can only grow in specific, little tucked-away corners of the world. And only the most patient and nurturing of growers can do it, really.

“Only somebody [who] really takes the time to understand Pinot’s potential can then coax it into its fullest expression. And then, I mean …

“Oh, its flavors are the most haunting, and brilliant, and thrilling, and subtle, and ancient on the planet!”

Miles’ analogy to himself is patently clear. But less – much, much less – would have been so much more.

Remarkable Virginia Madsen

On a more troubling note, Miles’ obnoxiousness makes Virginia Madsen’s job mighty difficult.

Why would the beautiful, sensitive, seemingly intelligent Maya fall for such a pathetic jerk? (In the book, she has her own less-than-rosy personal motives.)

After listening to Miles’ pompous monologue about the emotional needs of Pinot grapes, Maya should have gotten up and left, never to return. The fact that Madsen succeeds in making believable her character’s interest in Miles – without suggesting insanity – is proof of this underrated actress’ remarkable talent.

The day after

Unfortunately, not even Virginia Madsen can save Sideways from its predictable, audience-pandering conclusion: Regardless of what happens while on the road, Alexander Payne and Jim Taylor want us to believe that all will be well once you reach your destination.

At the movies maybe, but in life there’s always the day after.

Sideways (movie 2004) cast & crew

Director: Alexander Payne.

Screenplay: Alexander Payne & Jim Taylor.
From Rex Pickett’s 2004 novel. (The book was published only a few months before the movie came out.)

Cast: Paul Giamatti. Thomas Haden Church. Virginia Madsen. Sandra Oh. Marylouise Burke. Jessica Hecht.

“Sideways (Movie 2004)” endnotes

Besides the award wins listed further up, Sideways was the top awards-season choice among U.S.-based critics groups.

Thomas Haden Church, Paul Giamatti, and Virginia Madsen Sideways movie images: Fox Searchlight.

“Sideways (Movie 2004): Alexander Payne’s Overeager Crowd Pleaser” last updated in April 2023.