Review of Sideways (2004) by Evan J — 30 Apr 2014

Directed by Alexander Payne, who had made a name for himself with Election (1999) and About Schmidt (2002), along with co-writing partner Jim Taylor took on this adaptation of Rex Pickett's 2004 novel, which Payne had optioned before it was published.

It's a sunny yet melancholy look at middle age life during a week long break round wineries. The film makes for an entertaining and amusing little journey. Miles Raymond (Paul Giamatti) is a struggling writer who has had one book published and he's divorced and bordering on the verge of alcoholism.

To take his mind of things, he takes his college roommate and voice over actor Jack Cole (Thomas Haden Church), who is a week away from getting married, on a week long trip around Santa Ynez Valley Wine Country, where Miles, a wine connoisseur, wants to educate Jack on the pleasures of wine.

On the trip, Jack one last fling before marriage, and he finds it in winery employee Stephanie (Sandra Oh), who they meet through waitress Maya (Virginia Madsen), who Miles once had a relationship with, and he still has feelings for.

Payne has a knack for making brilliant films about people which on the surface look like comedies, but they're actually dramedies, which have moments of awkwardness which you feel guilty for laughing at.

But this has some brilliant performances throughout and a very witty and clever script.