Directed by Alexander Payne

Alexander Payne’s movies show people at their worst.  In Election a benign high school teacher stoops to new lows to interfere with a class election, About Schmidt is about a man Payne described as “a small man” who loathes his daughter’s benign husband, and Sideways is about a sad, failed writer and a sad, failing actor, both who are very capable of self-sabotage.

Miles (Paul Giamatti) and Jack (Thomas Haden Church) are middle-aged friends who seem like they’re only still friends because neither has anyone else to drink with.  They embark on a week-long trip up to Southern California wine country before Jack’s looming wedding.  As a wine aficionado, all Miles wants to do is drink, but all Jack wants to do is fool around with anyone and everyone.

This immediately sets up each character’s vice.  Miles doesn’t approve of his friend’s anticipated philandering, and Jack is very attuned to Miles’ drinking problem.  They are a study in opposites, only adding to the mystery of why they’re still friends, and each rubs the other the wrong way.  Still, they have some kind of bond, one which apparently dates back to freshman year at San Diego State.

Miles is depressed.  He’s a middle-school English teacher living in a cramped apartment and awaiting word on whether his novel is to be published or not.  Jack isn’t very sure about his marriage, but Miles isn’t the right person to turn to for advice considering he is two years removed from a marriage he still hasn’t gotten over.  His particular situation compels him to be jaded to marriage even as he remains unable to move past his divorce.

After a brief pit stop at the home of Miles’ mother, which establishes Jack’s degree of minor fame, the two of them make their way up to wine country and we meet Maya (Virginia Madsen), a friendly waitress who demonstrates a liking to Miles.  If it weren’t for Jack, Miles might completely miss these signs of polite affection.

The next day they meet Stephanie (Sandra Oh), and soon Jack is organizing outings for the four of them in hopes of getting himself and Miles laid.  And it works, for the most part.

Jack and Stephanie quickly begin a romantic, passionate relationship, and Jack claims that they both know it is nothing more than a fling.  Miles has his doubts, particularly as he overhears Jack call her “honey” on the phone just as he does with his wife whose phone calls he is now avoiding.

Miles’ time with Maya doesn’t go as smoothly, but eventually they sleep together, based on an attraction mainly towards each others’ fascination with wine.  When Maya learns from Miles that Jack is married, she gets angry and leaves.  Soon Stephanie is showing up at their hotel and attacking Jack, making it clear just how far apart her expectations were from Jack’s own.

Despite a moment in which Jack tells Miles he might call off the wedding, he now moves on from Stephanie with ease, showing how little she ever meant to him despite his professions of love.  He finds another waitress to sleep with, and when that doesn’t go as planned, Jack insists he now knows how much his wife means to him.

Miles will return home following the wedding and a brief rendezvous with his ex-wife who is now remarried and pregnant.  He is at his low point, sneaking in wine to a fast-food restaurant while the rest of the wedding party is at the reception, but sometime later he receives a voicemail from Maya who finally finished reading the manuscript he sent her.  Determined to take some action in a life which made him feel like “a thumbprint on a skyscraper,” Miles drives up north to visit Maya.  The film ends with him knocking on her door.  It’s less about what happens and more about the positive steps forward Miles has taken.

After reading Rex Pickett’s novel, Alexander Payne told him he liked the story because the characters were “so fucking pathetic,” and the film certainly doesn’t shy away from that quality, even as we find reasons to root for Miles.

He’s a character who’s not even rooting for himself, and his opposite is someone who has no self-awareness and is more eager to use a wedding as justification to hurry in his own affairs than as a reason to get married.

Both love interests, Stephanie and Maya, are too good for our protagonists.  You almost don’t want them to get sucked down to the guys’ level, but in the end Miles finally steps up to their level to earn our respect.

The film finds plenty of humor from the characters’ selfishness and on multiple occasions we’re able to see right through their facade.  Miles sneaks out of his mother’s house, skipping out on a lunch she excitedly organized for them, and in another scene Jack has to speak in a nasally, muffled voice through a bloody towel shoved over his face following Stephanie’s attack.

This attack leaves Jack with a large, unappealing bandage across his nose like that of Jake Gittes’ in Chinatown.  The effect is similar, to use this visual gag as a way to undermine a self-important and self-righteous character.  We see what he doesn’t about himself, but the injury also begins a brief, possibly vapid journey of self-discovery for Jack to realize how small he is.  It’s after this when he will finally admit how much he loves his wife, though whether or not we trust him is another story.

There is an odd effect at play in Sideways in which we’re fully immersed in an aesthetically beautiful world of wineries and scenic drives, but we’re dealing with characters who live on the fringes of this world or are only tourists here.  In this world they play the role of the social elite, and wine-tasting itself feels like a very high-class activity, but in reality they are just playing up to a certain image.  We see each character’s home, and for the most part they are all small, albeit appealing, apartments.  They live within their means in a surrounding environment that encourages indulgence.  In another sense, they just don’t belong here.

Sideways resembles something like an Eric Rohmer film.  He’s a French director whose films often deal with the insular ups and downs of a group of well-off characters.  They live in seaside villages or other communities which feel like bubbles from the real world, and their problems are romantic.  It matters who you’re sleeping with and who that rubs the wrong way.  Beyond that bubble, these problems mean nothing, and in some cases it asks a lot of the audience to care.

We do care in Sideways, maybe only because the film has a very strong sense of its characters’ self-pity and self-indulgence.  The film frames them as a mix of disturbingly sad and disturbingly self-righteous.  The fact that both Jack and Miles tries to keep the other in check demonstrates that they themselves aren’t too far gone from reality, and it does offer a strong emotional bond that helps ground the film.

Still, the film looks at its characters with a certain distance, suggesting that they are not people we strive to be like but they still deserve some kind of internal peace.  If the film were as taken with the characters’ fleeting fancies as they are, then it might be harder for an audience to stick with them.  It’s important, then, that Sideways is a comedy because asking us to laugh is easy, but asking us to empathize with Miles and Jack for two hours is asking a bit too much.

Up Next: You Can Count on Me (2000), Lone Star (1996), Magnolia (1999)