Review of Sideways (2004) by Sean W — 22 Jul 2011

Sideways is one of those great films that seems to get better with each viewing. The characters, the locations, the story . . . having seen the film numerous times now, it's a real pleasure to reacquaint myself with these colorful (yet deeply flawed) characters and spend a week in wine country with them.

Sideways tells the story of two friends, Miles (Paul Giamatti) and Jack (Thomas Haden Church). Jack is getting married in a week, and his best friend Miles is taking him on a tour through California's wine country to see the sights, taste a lot of great wine and relax. Jack is more interested sewing his wild oats, as it were. Miles, in the meantime, is struggling to get over his own inadequacy. The man's divorced and still hung up about his ex wife. Furthermore, he's unhappy with his place in life and while he's written a novel, there seems to be little hope of it ever getting published. The two men meet a couple women on their adventure, and that's where the proverbial plot thickens. The first is a waitress at a local restaurant named Maya (Virginia Madsen), who actually shows an interest in Miles. The second, her friend Stephanie (Sandra Oh), takes to Jack. The two men discover a few things about themselves, and drink a shit load of wine in the process.

Whenever I think of Paul Giamatti, and those quirky characters he's so great at playing, I think of Sideways. For me, this is the movie that totally made him "that guy." He's fantastic in the role. Obsessive compulsive about his passion, wine, and a touch immature on relationships. He's not a perfect person, but somehow you get behind his character. The same could be said for Jack. Thomas Haden plays, well, a pretty shallow character. But he's charismatic, and you can't help but chuckle at the lengths he'll go to for some attention. Watching these two characters bounce off of each other is a delight from scene one. They are so different yet you get a real sense of friendship there. You completely buy into it. Kudos to the actors for doing their part, and delivering their lines with some authenticity.

There's a scene in this movie that's one of the great scenes of all time. You know those movies, that have that one great scene that just floors you. Miles and Jack end up going on a double date, and heading back to one of the girls' houses. Jack and Stephanie are, ahem, preoccupied, and Miles and Maya find themselves alone for the first time. They head out onto the back porch to share and talk wine. Then the moment happens. The moment that every couple has when they realize they're really into someone. Maya sees past Miles' flaws and admires the passion he has. And then Miles asks a very simple question about how Maya got into wine. A simple answer could've been given but Virginia Madsen delivers a monologue and you see why Miles can't help but fall for her. The scene goes a step further, and Miles relationship flaws really shine through when he fails to capitalize on the moment that just happens. Furthermore, he tries to make up for it after the fact and fails miserably. It's a great couple of scenes that feel real. They're performed brilliantly and it's my favorite part of the movie.

Fortunately, the rest of the film is just as well structured. There's humor from top to bottom and the movie never runs out of steam. There's also a lot of great locales visited, and while the cinematography is a tad soft, that's intended. Listen, I can go all day gushing about this fucking movie, so I'll just cut myself off here and summarize. It's well-written, the actors do a phenomenal job and the story is great. But for whatever reason, this movie taps into something that brings you back for repeat viewings. That's what makes the movie so great. The fact that it creates something worth revisiting, and that it's a great trip each time.