Alexander Payne's Sideways is another great example of why unsuccessful writers tend to make much more interesting characters than successful ones. Their lack of acclaim feeds their view of themselves as "misunderstood", while their inevitable rejection serves as a wonderful device with which to bring their over-inflated egos crashing back into the real world. Miles Raymond (Paul Giamatti) is one such writer, whose life seems to be tumbling around him. Bordering on the alcoholic and with pockets lined with prescription medication, he sets out for a week of wine tasting in the Santa Ynez Valley with his soon-to-be-married friend Jack Cole (Thomas Haden Church). A wonderfully witty character piece unfolds as the two pair up with waitress Maya (Virginia Madsen) and her friend Stephanie (Sanda Oh), as their desires for either one last pre-marriage fling or a committed relationship start to raise tensions between the friends. A film about wine aficionados might not sound like the most thrilling prospect, but in the hands of Alexander Payne and co-writer Jim Taylor it becomes almost an extended metaphor for the foibles and peculiarities of Miles and his companion. Quite rightly, Payne and Taylor picked up the Oscar for Best Adapted Screenplay.
