Sideways (2004) review

Dir. Alexander Payne

By: Steve Pulaski

Rating: ★★★★

In the wrong hands, Sideways could’ve been a deadly, directionless comedy of errors, always setting up some joke even if the screenplay wasn’t exactly sure how it would employ the punchline. Or worse; the film could’ve taken lovable actors and stuffed them into a screenplay of landmines and incredulity as far as the eye can see, throwing them into pitfalls and clichés, with little to no development as characters beyond two self-pitying buffoons.

Thankfully, Alexander Payne, an actor who has kept a consistent run of great films, takes this material gently and professionally, allowing the film to inhabit close, methodical pacing in order to develop its characters, give them well-deserved on screen time, and provide us with some of the sharpest, most satisfying dialog in a dramedy in recent years. Sideways is alert, rather than inert, and careful rather than crass.

We follow along two wine-aficionados as they travel through the Santa Ynez Valley, tasting wine, and having a relaxing weekend before one of them weds his fiancée. Paul Giamatti is Miles Raymond, a dysfunctional, self-loathing cynic, as well as a struggling writer and pessimistic soul who is slogging through his dead-end career as a middle school English teacher. He once had a great wife, but now she is divorced, and is engaged to another man whom Miles has never met.

Our other protagonist is Thomas Haden Church’s Jack Cole, who sees this weekend less as relaxing escapism and more as one last chance to get some before he puts a ring on it. Jack is a longtime actor, and was Miles’ freshman roommate in college. When they hit the road, their first stop is at Miles’s favorite restaurant, where Maya (Virginia Madsen), an attractive waitress he has made small talk with before, catches his eye, and Jack eventually encounters Stephanie (Sandra Oh), a friend of Maya’s who works at a local winery. The four agree to double date, and this is where Miles hastily discovers Jack’s plan to have one final fling with this woman before he marries. He too discovers that Jack becomes sick with delusion, even going as far as to knowing the woman for less than twenty-four hours and propose the idea of opening a winery with the four of them.

Despite being a road movie, the film is a surprising study in emotion and kicks in a brilliant portrayal of ones midlife crises and the way someone can casually agree to situations while in denial of their current life. Paul Giamatti is an actor, with a distinct allure and an ability to convey subtleties in a commendable way, whether it is playing an unfulfilled wrestling coach, or a down-on-his-luck writer with a craving for the finest wine. Thomas Haden Church is equally impressive, usually providing lovable banter and frequently bouncing off his co-star’s character’s mishaps.

I was immediately won over by the picture, mainly due to its simplicity, yet its unmistakable amount of depth and intelligence behind it. The characters are flawed and undeniably imperfect, but that’s what makes them fun to watch. Their love for wine just fuels the screenplay’s wealth of interest and ideas, providing us with some of the most entertaining monologues this side of a comedy-drama. If a film can make me care so much about a topic I couldn’t care less about, wine is definitely one of those, than it is obviously doing something right. What could’ve detoured into truly mundane, vapid dialog is carefully guided down the route of wit and attraction, despite its apparent lack of relativity.

Alexander Payne has swung and hit one out of the park, this time, making one of the most enjoyable films I’ve seen in a blue moon. A film that somewhat restores my faith in modern cinema. Payne’s directorial debut was the wickedly smart and ferocious comedy, Election, centering its story around a spry young woman who becomes so determined to win a meaningless school election, she doesn’t realize one of her teachers is trying to run her into the ground. The film was filled with cleverly placed lines that brought smiles upon smiles, along with presenting a satire on the absurd idea on how a rationally thinking man can be pushed over the edge by an overambitious brown nose. Sideways is a step in a totally different, yet efficient direction. A captivating drama that truly embraces its simplicity and closely follows its characters, examining their flaws as humans, and showing us some of the most tender sequences that also happen to be bittersweet and poignant. It is a gem of many kinds.

NOTE: As of this writing, Sideways is available to rent on multiple platforms.

REVIEWS OF OTHER ALEXANDER PAYNE FILMS:
My review of The Descendants (2011)
My review of Nebraska (2013)
My review of Downsizing (2017)
My review of The Holdovers

Starring: Paul Giamatti, Thomas Haden Church, Virginia Madsen, and Sandra Oh. Directed by: Alexander Payne.