“Half my life is over and I have nothing to show for it. Nothing. I’m a thumbprint on the window of a skyscraper. I’m a smudge of excrement on a tissue surging out to sea with a million tons of raw sewage.”

There are two types of jerks in this world: those overwhelmed by a crippling lack of self-esteem, and those overwhelmed by a crippling excess of it. Sideways, directed by Alexander Payne (The Descendants, About Schmidt) and starring Thomas Haden Church and the criminally underrated Paul Giamatti, shows a small road trip with one of each type. The movie is subtle, deep, and complex, although not necessarily hard to follow. There are also a lot of smart wine metaphors and tidbits—so much so that this movie actually boosted the sales of Pinot Noir and hurt the sales of Merlot the year it came out. It’s also a great comedy-drama that I thoroughly enjoyed.

The plot centers on Miles, a middle school English teach and aspiring novelist, as he takes a road trip to wine country California with his old college friend Jack, an aging actor, to have one last hurrah before Jack’s wedding. Miles is still reeling from his divorce two years prior and is such a mess emotionally that he has trouble connecting with others. Jack isn’t quite sure he’s ready for monogamy and is determined to have as much sex as possible on the trip. While they meet attractive two women, they’re also dealing with the subtle and not-so-subtle ways that they’re unhappy with how their lives turned out. Though there are many plot points, the question under the surface is what will actually make each of these men happy.

No, if anyone orders Merlot, I’m leaving. I am NOT drinking any fucking Merlot!

This is a movie about a writer, and it’s very well-written. (It’s based on a book by Rex Pickett.) The nuanced inner turmoil of both Miles and Jack, as well as their complicated relationships with Stephanie and Maya are at once instantly relatable but so complex that you rarely see similar things in other movies. The movie deals with many Hollywood cliches: middle aged men questioning their own importance, a groom with cold feet, a man crushed by a recent divorce. This could easily have been just another Hollywood movie about those things, but writer and director Alexander Payne’s deep insight into human nature and his ability to portray it in his movies elevates this film to another level.

Miles lectures Jack on how to drink wine in Sideways
If you’re a wine snob or you know one, scenes like this are absolutely hilarious.

Sideways walks a meticulous line between tragedy and comedy, often showing both at the same time. The lead characters are pathetic, yet we empathize with them; their emotional struggles are sad, and yet both characters are hilarious; we shake our heads at what the characters are doing, yet we’re enthralled with those same actions. And there are satisfying resolutions to everything—not just the plot points, but the character growth as well. The ending, while as subtle as anything else in the movie, is very gratifying.

Sideways is one of the best-written films of its decade with deep insight into human nature and emotions. It’s also a fascinating portrait of the mid-life crisis many men face when they wonder if anything they’ve accomplished in life matters. While dark at times, the biting humor lets us laugh at what would otherwise be a joyless topic and makes the film much more watchable. It’s a tremendous success in both screenwriting and filmmaking with outstanding performances from all of its actors that deserves a spot on the watchlist of any serious cinema fan.

View my complete list of classic, essential, or just plain good movies!

Runtime: 2:07
Director: Alexander Payne
Year: 2004
Genres: comedy, drama, indie
Rating: R

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