Sideways is two hour tribute to drunk driving and friends who should all consider joining AA together. In it Jack, a voice-over advertisement actor, and Miles, the author of an unpublishable book, swing through California wine country. There they spend their time getting drunk and laid while trying to escape sordid reality -- Miles has just left a failed relationship with a controlling, belittling woman and Jack is about to enter one. The movie attempts to portray these two as realistic figures. The humor and pathos of the work is intended to emerge from the audience's sympathy and horror at their mid-life crisis and their awkward attempts to make their ways through life. Miles in particular is supposed to have a certain every-man charm, as seen in the fact that he has an ordinary lifestyle with an ordinary job (as a middle school English teacher) and his relatively conservative approach to sexuality. Despite the fact that Miles and Jack are obviously meant to appeal to the audiences experience, they share a lifestyle which is far removed from middle America. The variety of lifestyles that exist in so-called "everyday life" --and especially everyday life in California -- are so wide ranging that it is impossible to make any categorical statements about it. It is surely likely that people precisely like Jack and Miles exist somewhere, for their dialogue and antics seem quite human, if not quite normative. However, the screenwriter's perception of how normal people in America live is obvious a little skewed. .

             There are several ways in which Miles and Jack are atypical of normative Americans. Most Americans do not have the sort of money it requires to take a week off and go driving through wine country, staying at expensive resorts and drinking entire bottles of wine which may be over $100 a bottle (going rates on wine from vineyards in the Napa area appear to be from the low twenties to almost $300 a bottle).