Released 2004
Stars Paul Giamatti, Thomas Hayden Church, Virginia Madsen, Sandra Oh
Directed by Alexander Payne

Two men go on an excursion and end up inducing midlife crises in this comedy-drama that won six Independent Spirit Awards, including Best Feature and Best Director. Pinot Noir lover Miles (Paul Giamatti) convinces friend Jack (Thomas Haden Church) to enjoy his last days of bachelorhood with a wine country road trip. The pair get involved with two women (Sandra Oh and Virginia Madsen) and inevitably come face to face with their past and present.

Summary by http://www.netflix.com

When the Oscar nominations for Best Picture were announced, this selection surprised me the most. I hadn't seen any of the five, but "Sideways" seemed like too small and personal of a comedy to be nominated. Now that I've seen it, I understand completely. This is a great film. It's a wonderful mix of drama and comedy, and it's almost my favorite movie of 2004. My favorite scene was where Miles described his love for Pinot Noir, which was followed by Maya's response about her love of wine. She described how each wine is unique and evolves throughout its life until it finally peaks. Of course, they were describing themselves and their own lives in terms of wine. It's one long subtle, moving moment, and it's one of the best movie moments of the year. Watch their body language and facial expressions. Ever so subtly, their eyes soften, they drop their guards and essentially fall in love. It's brilliant dialogue but also brilliant acting, and that's true of the whole movie. --Bill Alward, April 16, 2005