Sideways

Sideways (2004). Director: Alexander Payne

Sideways is a film directed by Alexander Payne that came out in 2004. It belongs to what’s called the “road movie” genre, where the story unfurls along some sort of trip that the main characters embark on. In Sideways, Miles, a dejected English teacher who has been struggling with his dream of becoming a writer and with getting over a failed marriage, takes his best friend Jack, an actor who is well past his prime, to a wine-tasting tour before Jack’s upcoming wedding. However, the two friends set out for the road trip with different things in mind. Miles wants to have a good time with his buddy; Jack on the other hand just wants to have one last fling before getting married. Things happen along the trip, and we get to know this contrasting duo more. Interesting enough, Miles and Jack together, each flawed in his own way, make Sideways one of my favorite movies of all time. 

One great thing about Sideways is the characters of this pair of friends, especially Miles. He is depressed, gloomy and weak-willed. But all the negative qualities that make Miles ordinary (or sub-ordinary even) also make him perfectly relatable; he represents a little bit of you and me with his flaws and weaknesses. Compared with an antihero that wins an impossible battle at the end of the story, Miles’ story may be less victorious but is absolutely more comforting. Despite all those loser qualities in Miles, there’s indeed something good about him, and that is his gentleness and sensitivity. And of course his knowledge in wine. One very touching moment in the movie is when Miles is explaining to a love interest why he is so obsessed with Pinot, a grape that has a very tender nature and therefore can only survive with constant care and attention. The similarity between Miles and the grape he likes cannot be more obvious, although it seems to me that Miles doesn’t intend to use Pinot as a metaphor to reveal anything about himself at that moment. During those few minutes, Miles the loser shimmers from within, which I find immensely moving. Another of my favorite Miles moment is when he find out his re-married ex-wife is now pregnant, he opens the wine that he’s been saving for years for a non-specified special occasion (presumably when his ex-wife comes back to him) and savors it at a fast food restaurant with a burger and some onion rings. There is no tear, and Miles doesn’t even look sad. But that’s one of the most heartbreaking scenes I’ve ever seen. 

Jack provides a sharp contrast to Miles. He is everything that Miles is not: cheerful, impulsive, selfish, shallow and, most importantly, almost nothing troubles him. Jack makes all the troubles and gives us the laughs along the trip. He is the comedic element in Sideways and balances Miles’ misery with his recklessness. Jack is like the sun, but the point is not to show you how bright he is, but to bring your attention to the shadows, and that is Miles. Although I like Miles more and has much less to say about Jack, the story will nevertheless be much inferior without him. I’d like to think that Miles and Jack likely present two people with contrasting qualities for the audience to relate to depending on their own personalities. Who would you rather be? Miles or Jack? 

I am glad that the story ends on a positive note for Miles, and that is the comfort I mentioned earlier. Miles may be a downright loser by various definitions, but there’s something about him that is worth appreciating. At the end, he finds someone to appreciate him for who he is, and I find comfort in that Miles, who is not a hero (or antihero), finds a good ending.