Movie Review – Sideways

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Sideways (2004)
Written by Alexander Payne & Jim Taylor
Directed by Alexander Payne

With Sideways, Alexander Payne caused a 16% increase in sales of pinot noir in the Western United States. How many movies can say they did that? It also increased tourism to the Santa Ynez Valley in Central California and decreased merlot sales by 2%. I remember seeing this movie while I was in college with my friend Sam. In the following months, he became more interested in wine, and I benefitted by getting to try a lot of it. I can’t say I like wine all that much. I always seem to get a headache the morning after. I think the magic of this film is that even if you don’t care about it, the writing makes you interested. This is the effect of having a genuine passion; the rest of the world becomes invisible when you are lost in it, yet often you become someone people flock to because of that passion. We all want to feel that way about something.

Two friends embark on a week through California wine country. Miles (Paul Giamatti) wants to show his soon-to-be-married friend Jack (Thomas Hayden Church) the beauty of the landscape and the wine. Unfortunately, Jack is more interested in having a fling before he’s married and never really commits to the trip. There’s also Maya (Virginia Madsen), a local waitress who knows Miles from his previous visits to the region. Sparks fly between the two, but they’ve always been with other people, so the opportunity has never arisen until now. Jack hooks up with Stephanie (Sandra Oh), a wine pourer and friend of Maya’s but doesn’t disclose his pending nuptials. Miles feels stuck in the middle, sinking deeper into Jack’s lie while growing closer to Maya. He knows that the truth will eventually come out but doesn’t understand how devastating it will be.

At the center of Sideways is the story of a person coming to terms with the fact that they are entering middle age without achieving nearly any of their dreams. Miles had aspirations to be a great writer, and he has a novel. Unfortunately, it’s bloated and unwieldy, something his editor tells him isn’t bad but isn’t marketable to publishers. Miles doesn’t want to compromise his vision but writing this novel took a lot out of him; he’s not sure if he can write another. It’s also evident that he hasn’t processed his divorce and that it shook up his self-worth; he still drunk dials her despite his ex-wife having remarried. Miles lived with the assumption that his life, like his wine, would get better with age. It did not. 

The title Sideways has several meanings in the context of the film. We lay wine bottles on their sides in storage to help the wine age properly. There’s also the phrase “things have gone sideways,” meaning that a situation has gone much more poorly than anticipated. The challenges Miles is facing are ones that he must reckon with; they concern the very nature of how he perceives himself and the idea of being in an intimate relationship. Jack is also not doing too hot. He’s only recognized from his role in a soap opera a decade prior. He admits that the acting work is drying up as he ages. So how does Jack deal with their own midlife crisis? He gets engaged and then ravenously cheats on his fiancee in the lead-up to the wedding. Miles is sure that he doesn’t want to live like Jack, but he’s also becoming disturbingly comfortable with getting blackout drunk and living in his depression.

Payne does his best balance of comedy and drama in Sideways, delivering a story that doesn’t cater to maudlin sentiment. These are realistic people in a realistic scenario making terrible choices and trying to figure out how to fix the damage once it is done. Miles isn’t a saint; he steals money from his elderly mother when he and Jack stop off for a night. He promises to go to breakfast with her and his sister’s family the following day and then skips out at dawn. Miles uses Jack’s lie to get closer to Maya and is just as callous about Stephanie’s feelings as Jack. Jack is a very unlikeable guy, but we can also see how he’s used his charm to skate through life, something that has faltered with age.

There’s a good argument that Payne should have stopped after this movie. I personally do not think his work has shown great promise since and instead has become mired in a lot of anger and misguided choices. We’ll get into that with the following reviews, but I’ll say Sideways feels highly confident. It’s undoubtedly skewed to a male perspective but certainly not a forgiving one. The film is tough on Miles, and it’s up to him to be humble and fix things with Maya in the end. Like About Schmidt, we’re left not knowing if things will get better. They could. He could also slide back into old habits. The movie is about coming to that moment where you realize things have to change; that’s when the work actually begins.