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‘Sideways’ Movie: Days of Wine and Losers

Sideways Movie Paul Giamatti‘Sideways’ movie: Paul Giamatti and Thomas Haden Church enjoy days of wine and women.

‘Sideways’ movie review: California winery tour follows conventional road to male maturity

With the 1999 Matthew Broderick-Reese Witherspoon vehicle Election, Alexander Payne displayed a flair for satirical comedy the likes of which would have turned Billy Wilder greener (with envy) than the Sideways poster found further below in this commentary. With the 2002 Jack Nicholson star vehicle About Schmidt, Payne demonstrated that his comedic flair could go the way of Wilder’s in fluff like Sabrina and Love in the Afternoon: bland, cutesy, phony.[1]

In Sideways, Payne opted for the safer About Schmidt route – which helps to explain the film’s enormous popularity with critics and audiences alike. Except, apparently, with this reviewer, who found his adaptation – with Jim Taylor – of Rex Pickett’s novel to be an overlong, moralistic, and unabashedly dishonest effort. (Warning: This Sideways movie review contains spoilers.)

‘Sideways’ summary

At its core, Sideways is a road movie about two middle-aged men – who should have been killed at birth – learning to grow up. The film’s problems begin with the trip itself, as divorced high school teacher and writer-wannabe Miles (Paul Giamatti) and former TV soap star turned TV commercial announcer Jack (Thomas Haden Church) take a longer than necessary road trip to Central California’s Wine Country. One week of driving, fighting, and boozing up adds up to 124 never-ending minutes of screen time.

The duo’s little wine-guzzling excursion is supposed to be Jack’s farewell to his much cherished bachelorhood, which will be over the following Saturday when he marries the wealthy Christine (Alysia Reiner). While visiting Central California’s bars and wineries – Miles is a wine connoisseur – they run into two local women, Maya (Virginia Madsen) and Stephanie (Sandra Oh).

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

Lies and betrayals lead to unexpected confessions that lead to angry outbursts that eventually lead to various contrived self-analyses and an even more absurd promise of reconciliation. Sadly, despite all that angst, no one thinks of committing harakiri on camera.

Sideways movie Thomas Haden Church Paul Giamatti. Arrested coming-of-age flick critics' faveSideways movie with Thomas Haden Church and Paul Giamatti. Alexander Payne’s belated coming-of-age road movie obviously pleased the members of the Los Angeles Film Critics Association; Sideways won five awards: Best Film, Best Director, Best Adapted Screenplay (Payne and Jim Taylor), Best Supporting Actress (Virginia Madsen), and Best Supporting Actor (Thomas Haden Church).

Crowd-pleasing beating

Admittedly, 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 – this reviewer almost felt sorry for him. But no tears were shed for Stephanie, for this thirty-something woman should have known better than to think that two days of wild sex implied a life-long commitment.

By the way, the violent scene between Stephanie, the physical aggressor, and Jack, the victim, is played for laughs. Now, imagine if the situation had been reversed, with Church’s character as the “betrayed” party punching the deceitful Stephanie on the nose. Just think of how funny-haha that moment would have been.

Sideways movie Virginia Madsen‘Sideways’ movie, with Virginia Madsen.

Epiphany and the dangers of self-parody

Later on, Thomas Haden Church’s Jack has a major dramatic moment: that’s when the grown man realizes what a boy he has been. The screenplay offers no help, but Church is way out of his range in that scene even though he earns points for avoiding 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 – despite everything we’ve seen until then proving the exact opposite.

Self-pity and the dangers of overwrought dialogue

Wallowing in self-pity, Sideways’ straight (and morose) man Paul Giamatti tries much too hard to be likable; as a result, he fails miserably. I must admit, however, that I found Alexander Payne and Jim Taylor’s (widely admired) dialogue equally to blame. One instance, not found in Rex Pickett’s novel:

Virginia Madsen’s Maya:
“Why are you so into pinot? It’s like a thing with you.”

Paul Giamatti’s Miles:
“I don’t know. It’s a hard grape to grow. As you know, 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 and in fact can only grow in specific little tucked-away corners of the world. And only the most patient and nurturing growers can do it really, can tap into pinot’s most fragile, delicate qualities.

“Only when someone has taken the time to truly understand its potential can pinot be coaxed into its fullest expression. And when that happens, its flavors are the most haunting and brilliant and subtle and thrilling and ancient on the planet.”

Miles’ analogy to himself is clear. But less – much, much less – would have been so much more. (Most others apparently disagree, as this little exchange has been quoted ad nauseam as a representation of brilliant movie writing.)

Then we have Miles’ devotion to his mentally and emotionally stunted actor friend; loyalty that goes way beyond the realm of friendship and right into the realm of idiocy. That’s why it’s this peace-loving viewer found it all but impossible not to root for a local husband-gone-berserk to give Miles the beating of his life in Sideways’ painfully unfunny comic climax. Tragically, to no avail.

Virginia Madsen beautifully overcomes her character’s limitations

On a more problematic 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, the character has her own less-than-rosy personal motives.)

After listening to Miles’ pompous little monologue about pinot grapes, Maya should have gotten up and left, never to return – except that that would have destroyed the fairy tale. The fact that Madsen succeeds in making her character’s interest in Miles wholly believable without coming across as mentally unbalanced is proof of this underrated actress’ immense talent.

Sideways movie poster‘Sideways’ movie poster.

The crowd-pleasing route: Phony & conventional resolution

Sideways ends on a note that is both predictable and dishonest: Jack has an elaborate wedding and Miles drives back to the wine country to see Maya, with whom he had previously had a falling out. He knocks on her door, which slowly opens for him.

According to Alexander Payne and Jim Taylor, all is well that ends well. At the movies maybe, but in life there’s always the day after.

[1] For the record, the generally well-regarded Sabrina (1954) earned Audrey Hepburn a Best Actress Oscar nomination. Her co-stars were Humphrey Bogart and William Holden in a blond wig.

Love in the Afternoon (1957) starred Audrey Hepburn, Gary Cooper, and Maurice Chevalier.

Sideways (2004).
Director: Alexander Payne.
Screenplay: Alexander Payne and Jim Taylor. From Rex Pickett’s novel.
Cast: Paul Giamatti. Thomas Haden Church. Virginia Madsen. Sandra Oh. Marylouise Burke. Jessica Hecht. Missy Doty. M.C. Gainey. Alysia Reiner. Shake Tukhmanyan (as Shaké Toukhmanian). Shaun Duke (as Duke Moosekian).


Sideways cast information via the IMDb.

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

Sideways movie poster: Fox Searchlight.

Sideways Movie: Days of Wine and Losers” last updated in July 2019.

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