Alexander Payne's (2004) film "Sideways" reveals the tale of friendship between two middle-aged men who have been friends since college, Miles and Jack. Miles is a middle-school English teacher whose marriage has failed and whose novel has not sold. His friend Jack is getting married in a week, but Miles, also a wine connoisseur, abruptly informs him he is taking him on a week long bachelor party in California wine country. It seems that Miles may be a true connoisseur by day but by nightfall he is always drunk. Miles has named his novel "The Day After Yesterday," what today typically feels like to an alcoholic (Payne 2004).
Jack is a would-be actor who tells people he does commercials, but he really is the voice at the end of them that speeds through the side-effects details or other non-featured information. While on their trip they meet two women, a wine pourer named Stephanie and a waitress called Maya. Miles actually knows Maya and has loved her for years, but he has never summoned the courage to approach her with his intentions. Jack falls for Stephanie in what appears to be more than a last fling before marriage. As Miles says when he tells him he is in love, "In love? Really? 24 hours with some wine-pourer chick and you're fucking in love" (Payne 2004). Despite their differences, Miles and Jack work together because between them they almost make a complete human being. Their trip is one of "male self-discovery" and "bonding," in the view of film critic Carla Meyer (1).
The film is a comedy but also tinged with sadness and depth as Miles deals with the frustrations of middle-age and the mistakes he's made in life. Maya represents a chance for genuine love and meaning in his life. During one scene he explains to her his preference for the pinot noir grape but he is actually describing himself to Maya, including having a thin skin and being vulnerable. Roger Ebert (1) says of this sce...