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

Paul Giamatti, Thomas Haden Church, Sideways
DAYS OF WINE AND LOSERS

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 poster on the right. With About Schmidt, Payne demonstrated that his comedic flair could go the way of Wilder's in fluff like Sabrina: artificial, cutesy, bland.
In Sideways, Payne opted for Schmidt's safer route — which may explain the film's immense popularity with critics and audiences alike. For my part, I found his adaptation (with Jim Taylor) of Rex Pickett's novel to be an overlong, superficial, and thoroughly unconvincing effort. [Note: This review contains spoilers.]
At its core, Sideways is a road movie about two middle-aged men — who should have been killed at birth — learning how 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 added up to 124 never-ending minutes of screen time.
The duo's little 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 the local bars and wineries — Miles is a wine connoisseur — they run into two local women, Maya (Virginia Madsen) and Stephanie (Sandra Oh).
Maya is a fellow wine connoisseur, a talent that helps her bond with Miles, still depressed by the fact that his ex-wife left him and is now married to someone else. 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, no one thinks of committing harakiri on camera.
At least Thomas Haden Church manages to make his tanned, stupid, egocentric, and perennially horny actor (is there another kind in movies?) borderline tolerable. In fact, when Jack gets a broken nose — courtesy of Sandra Oh's irate Stephanie — I almost felt sorry for him. No tears were shed for Stephanie, however, for this thirty-something woman should have known better than to fall in love with Jack after two days of wild sex.
By the way, I should add that the violent scene between Stephanie and Jack is played for laughs. Now, imagine if the situation had been reversed, with Haden's character as the betrayed party punching the dishonest Stephanie on the nose. Just think of how funny hah-hah that moment would have been.
Later on, Church has a major dramatic moment; that's when the grown man realizes what a boy he has been. The screenplay (or perhaps the source novel) is no help, but Haden 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.