The Film Canon: Sideways (2004)


The biggest compliment I can give Sideways is that it is unconventional. Reading the plot description, it may sound like a typical road trip movie centered around two middle-aged men. That premise is still the basis of the film, but director Alexander Payne creates a unique twist on convention. Neither man is incredibly likeable or even fully imbedded with common sense. Both make stupid decisions and have different goals for the trip. These are played for laughs at times, but at other times not so much. Many scenes are downright hysterical, but others are layered with underlying tragedy. The title perfectly summarizes the direction of this movie. It goes all over the place both in story and tone. Ultimately, it’s all about the journey, not the destination.

Paul Giamatti portrays Miles, a character with little going right in his life. He’s an aspiring writer fighting to get his novel published, is stuck teaching middle school English and recently suffered through a nasty divorce. His one loving obsession in his life is wine. He decides to take his best friend Jack (Thomas Haden Church) on a road trip to wine country to celebrate Jack’s upcoming marriage. Jack’s almost a polar opposite of Miles. He’s good looking, a successful actor and entering a healthy relationship. They’ve been friends since college and argue like expected. Jack’s obsession is women and he vows to get Miles laid before the week is out. Putting them both together makes a complete individual, as both men have shortcomings the other compensates for and vice versa. This week-long odyssey adds up to a very moving film which is surprisingly human considering the lead characters.

At the heart of Sideways is the character of Miles. Giamatti perfectly encapsulates the depressed state of a middle-aged man with no direction. It is inferred his drinking caused the split with his wife. (He still dials her late at night completely drunk.) He even steals money from his mother. At the same time, we identify with his persistence and aspirations of becoming a writer. He’s not condoned by the film, and in many ways is the more knowledgeable of the two men. He allows for few things to slip by him, but his narrow sight and intimate nature prove to be his biggest flaws.


Jack is identifiable only through his constant lust for life and womanizing attitude. By the same token, he’s a bit of an idiot because he never seems to think about the consequences of his actions.  He’s getting married after the trip but enters a romantic relationship with a wine pourer played by Sandra Oh. Miles even calls him out on this and Jack’s response is completely illogical. He’s not exactly an idealist, but rather a man who only thinks within the here and now. Both actors work well together, it’s easy to see they’ve been best friends, hence the arguing seems genuine and true to how best friends fight.

Miles isn’t alone in romance either; we get to see him connect with another recent divorcee Maya (Virginia Madsen). What helps to sell this is the fact that Miles and Maya are acquainted prior to the beginning of the film as he is a frequent customer of the restaurant Maya waitresses at. The women aren’t shoehorned into Sideways for cheap schlocky romance, they are an intrical part of the story and even serve as a form of therapy for Miles.  My favorite scene of the film centers on Miles and Maya engaging in conversation about wine. Both describe their fixations on wine such as the grapes, texture and ultimately vulnerability. Both realize it describes them individually. It’s beautifully written and acted, reflecting how real people talk to one another. The screenplay co-written by Payne and Jim Taylor adds to the humanity of these characters. They always feel like real people and their problems don’t feel tacked on.  There’s never a moment where I saw actors; I saw complex individuals learning about themselves.


Sideways is never too sour or too somber for its own good. There’s a variety of humorous scenes, such as Miles teaching Jack how to properly taste wine only to discover he was chewing gum. There’s also an equal amount of downbeat moments mixed with dark humor; Miles is told that his book didn’t get the green lite for publishing. He rushes back into the winery in a fit of rage and proceeds to chug the bassoon filled with disposed wine. It’s funny visually, but tragic considering his dream went up in smoke. This makes the whole film rather unpredictable. There’s a scene where Jack loses his wallet and Miles must go and retrieve it. Due to the film not having a defined tone, we don’t know if this scene will be funny or dramatic. It makes the film feel that much more real. Life has both humorous and dramatic moments, after all.

Setting the film in the heart of wine country enriches the experience and shooting on location adds an amount of déjà vu for viewers who have been there. You may even see yourself in these scenarios or characters. I’ve personally never been, but Sideways reminds me of a great wine; it gets better with age.  There’s always something to gain from a view, whether it’s laughs, comfort or even a moment of self-examination. Like all of Payne’s films, the plot is not traditional, but the situations and characters mirror real life. Not all of it is positive but then again the most memorable moments in life can be either positive or negative. It’s one of the best movies of the 2000s for giving a touching and heartfelt look at the ups and downs of life.

Matt is a 21 year old film buff and recent graduate from The University of Rhode Island. Growing up in a small town in the smallest state, Matt began developing a taste in film and general geekdom at a young age. After years of watching various DC and Marvel animated television shows as a boy, Matt has become quite the afficinado in the realm of comic books. Towards the end of middle school, Matt began delving into the world of film by watching anything he could get his hands on. Nowadays, his tastes range from classic film noir and the mindbending works of David Cronenberg to the latest trends on the independent scene. Don't worry; he's still one for the latest film in the Marvel Cinematic Universe or DC animated adventure. Comics aren't the only source of literature Matt enjoys. He can sometimes be spotted reading the works of Stephen King or even the plays of William Shakespeare. As an aspiring film critic and screenwriter, Matt is always looking for inspiration and new ideas.