2. Sideways (2004)
Based on the book of the same name, Sideways tells the story of Miles (Paul Giamatti) and Jack (Thomas Haden Church), two college friends embarking upon a road trip through California's wine country before one of them is to be married. While it's Miles' intention to have a good time drinking various wines, Jack has an ulterior motive, that motive being one last sexual escapade before he walks the aisle. With Miles having been out of the game for two years after a divorce, Jack justifies his actions by assuming he can afford his friend the same luxury. Eventually, Miles gives in and plays along as they meet two women and weave a web of deceit and lies. Both Jack and Miles learn a valuable lesson by the film's end. Though their actions are deplorable throughout, the initial plan backfires on them when they actually fall for Maya (Virginia Madsen) and Stephanie (Sandra Oh), the two women whose paths they cross. For Miles, Maya is a big deal and a potential partner. Their interest in wine and literature is what brings them together and makes it easy for them to move past their previous partners. Jack and Stephanie start their relationship off in a more physical manner, but evolves from there, however he has so much more to lose. Eventually, as one would expect, the plan crumbles and they're exposed for who they are and their motives. Both men in the film are in their mid-forties and are seemingly trying to progress in life by adhering to certain social formalities, but in doing so have found that these formalities aren't necessarily conducive to their betterment. Miles is an introvert and terrified of stepping into another marriage because of this, and Jack is just as afraid of commitment. In many ways, the road trip and Jack separating himself from Miles, forces Miles out of his shell and into the arms of someone that genuinely cares for him and that he cares for in turn. Jack, on the other hand, learns the hard way that the facade he's put up would only gain so much mileage. It's an illusion that he could've very well kept up and left his soon to be wife for, but eventually Miles' honesty slips through and shatters any delusions he may have had. It's only in that moment that both men realize their own worth and what could truly be waiting for them if they simply look forward. I think Rex Pickett had written something profound when he released the novel and director Alexander Payne perfectly framed the tone. It's one of the few films that I feel directly tackles the issues of commitment and progressive relationships and manages to capture them in a way that has changed the way we look at modern romantic films. It seems a natural progression in this genre specifically, and it does it so effortlessly.