500 Movie Challenge: Sideways

SidewaysLike a lot of movies that are making their way into the challenge, Sideways is a movie that’s been recommended to me for about five years. It’s a favorite of movie nerds from the Pacific Northwest, often paired with Adaptation. So on a particularly rainy day, I popped in this hot mess.

The gist: Miles is a wine nerd. His fiction book has been rejected by a bunch of publishers and his wife left him, but he is a wine nerd and proud of it. It’s his passion, and what makes him happy no matter what goes wrong. His best pal Jack is getting married soon, so he organizes a road trip up and down the trail of wineries in Napa Valley. Just the two dudes, sipping wine and playing golf as single bros one last time. It’ll be great!

Turns out, Jack knows absolutely nothing about wine. He also doesn’t care to learn. Most relevant, he is a massive d*ck. The trip devolves into Jack ditching Miles several times to have sex with a wine pourer they meet during their tour. The plan was to tour wineries with his likely-depressed friend on what is supposed to be a guys-only vacation. There are plenty of sad montages of Miles trying to have fun by himself.

But Jack finds himself doubting the reasoning behind getting married. As his affair with the wine pourer deepens, Miles simultaneously finds himself involved with a waitress he knows from all his trips to Napa Valley. Intrigue all around! But no one is mentioning that Jack’s due to get married in seven days.

What I “learned”: The best lesson someone can learn in life is self-preservation. I hated Jack so much while watching this movie, and kept waiting for the moment when Miles would have a screaming fit and call him out Harold style. But it never happened. Miles has no self-protection, no preservation when it comes to Jack. He won’t stick up for the boys-only trip that he originally wanted, probably because he was afraid of losing Jack just like his wife. And Jack doesn’t ever thank him for his sacrifices. Horrible. I hope that character dies in a fire.

See this movie if you like: Movies about adulthood that don’t follow a traditional “it gets better” format. There is no hardline happy ending for Miles and Jack. There’s no clear lesson to Sideways except that sometimes stuff works out and sometimes it doesn’t. It’s up to the viewer to decide the lesson to be learned. For a coming-of-age film set with middle aged adults, this is very unique.

Avoid this movie if: You can’t stand Sad Sack characters. Miles is a Sad Sack through and through. But he grows on you. Your level of pity for Miles rises as the plot gets crazier, and you actually grow to like and understand him. You have to wade through a fair amount of nonsense to get there, though. If you’re not up for that two-hour journey, best not to jump in. You’ll only frustrate yourself.

New Films Watched: 32

Films Re-Watched: 0

Total Number of Films: 32

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