58. Sideways

Sideways (2004)
Directed by Alexander Payne

An incredibly rich and character driven film, Sideways has been one of my favorite films from the first time I watched it. There is a lot of insight in contrasting and comparing the two different personalities of Paul Giamatti’s uptight Miles and Thomas Haden Church’s carefree Jack. Giamatti and Church (who have great chemistry here) imbue their characters (which are already rather complex) with such great subtlety and idiosyncrasies that is hard not to root for the both of them.

However, Payne’s adaptation is unsparing on both of our lead characters. These are not great guys who do one or two wrong things; these are people with major flaws and issues. It’s refreshing to see a film deal honestly with characters that are layered with pros and cons. In fact, half the fun of the film is to watch the interplay of these two performances and the insight that comes from it.


Speaking of insight, Sideways employs several wine metaphors to deepen and illustrate our characters as well. There is an absolutely magic scene near the middle of the film where Miles and Maya (played by Virginia Madsen) discuss why they love wine so much; it’s worth the price of admission alone (and it nearly won Madsen an Oscar).

Have I mentioned that this is also one heck of a comedy? It really is. With the exception of a scene near the end of the film where Miles finds himself running away from a naked fat guy, all of the jokes are spot on. There is also some incredible music and editing work here that rounds out the film as a whole. If it wasn’t for that oddly gratuitous scene with the naked fat guy (and also his wife), this film might’ve found itself in my top 50, but its just such a big misstep that I can’t look past it. Beyond that, this film is pitch perfect and required viewing for me.