Sideways (2004)

In director Alexander Payne's insightful comedy adapted from Rex Pickett's novel:

• the Santa Ynez Valley wine country soul-searching road-trip of two middle-aged characters:
  - depressed and failed novel writer, San Diego English teacher and wine enthusiast Miles Raymond (Paul Giamatti)
  - ex-soap star lothario Jack (Thomas Haden Church) and about-to-be-married
• their encounters with Hitching Post waitress Maya (Virginia Madsen) and single mother Stephanie (Sandra Oh)
• the scene of shared wine passion in which Miles explained to Maya how he viewed himself as a pinot noir: ("It's thin-skinned, temperamental, ripens early...Only somebody who really takes the time to understand Pinot's potential can then coax it into its fullest expression") and her extolling of wine for its evolving nature: ("...I like how wine continues to evolve. Like, if I opened a bottle of wine today, it would taste different than if I'd opened it on any other day. Because a bottle of wine is actually alive and it's constantly evolving and gaining complexity. That is, until it peaks like your '61. And then it begins its steady, inevitable decline. Hmm. And it tastes so f--king good")
• the hilarious scene of Miles' retrieval of Jack's wallet in the bedroom of his latest conquest - a married woman: ("My friend was the one balling your wife")
• the last lines of the film - Maya's answering machine message: ("Don't give up, Miles. Keep writing. I hope you're well. Bye") listened to by Miles - followed by the poignant shot of Miles -- after having driven back to the Valley -- knocking on Maya's door