Sideways (2004) – Alexander Payne

Movies can stay with you. I remember seeing Sideways when it hit theatres, laughing with my friends as Paul Giamatti and Thomas Haden Church tried to figure out their lives, loves, and wine. The characters and moments stayed with me, not to mention the talented female leads of the film, Virginia Madsen and Sandra Oh.

There’s so much to enjoy and take away from this wonderful little film.

Set against California’s beautiful wine country, Miles (Giamatti) and Jack (Church) are approaching middle age, and neither of them appear to have achieved a great deal with their lives. Miles is the center of the film, a struggling writer, with the potential of a book deal teasingly on the horizon, and while he may love his wine, he is haunted and unable to let go of his ex-wife, who he learns has recently remarried.

Jack is a struggling actor, about to be married, and inducted into her in-laws’ business. He and Miles have planned for a week-long escape, traipsing across wine country, drinking, and if Jack has his way, getting laid a lot. Sure he’s about to get married, but this is his last chance to go on the prowl, and he’s not going to let Miles’ downer attitude ruin the week.

Enter Maya (Madsen) a local waitress working on her horticultural diploma, and Stephanie (Oh) who works at one of the local vineyards. The ladies click with Miles and Jack respectively, but secrets, lies, and just not the right time, are going to interfere with anything as each character goes on their journey.

Miles is incredibly relatable to me. I write, I like my wine (I currently work in a wine store) and he can be a bit of a downer as he struggles with his mental health. Sounds very familiar.

Jack keeps his insecurities and issues a little more restrained, but he still has them. In fact, none of the characters are exactly what their first appearance would suggest. They each have their own lives, pasts, issues, and fears.

It’s a miracle that any of us can find connections considering the problems we all carry around. Dealing with them against gorgeous sun-drenched vineyards seems to make them all the more grounded and relevant. It’s easy to get lost in our own problems and ignore the beauty of our surroundings, or those who inhabit it.

The cast is simply wonderful, they feel real, flawed, and no matter how attractive they may appear, they all seem grounded in reality, making the characters, situations, and moments relatable and reflections of things we ourselves may have gone through.

A charming, and wonderful film, that because of a single line, directly impacted the sales of merlot that year. A true delight that just gets better with age, like a fine wine.


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