In Sideways – Alexander Payne’s most bittersweet comedy to date – men on the verge of emotional breakdowns need to take a dangerous journey into the deepest parts of their minds, in order to challenge all the incoming problems, and – ultimately – accept their better feelings. To find solace and tranquility in life is an uneasy task, and the characters of the picture learn that harsh lesson very quickly, just as they traverse through the sunny, chic wine country of California.
Miles (Paul Giamatti) and Jack (Thomas Haden Church) are two middle-aged buddies, who decide to spend a few days roaming around various vineyards tasting wine and eating good food, just before the latter will take the trip down the aisle. Miles is both an unsuccessful, nerve-racking writer and a passionate wine lover. Even though he tries to enjoy his time, he still can’t forget about the fact that his wife has left him a couple of months ago. Jack is a struggling actor, a former TV star, and a desperate playboy, who will jump at every opportunity to get laid. His laid-back attitude and quirky humor make a local girl named Stephanie (Sandy Oh) fall in love with him. While Jack is having a good time doing wild things with his new partner, Miles is striving to impress a pretty woman Maya (Virginia Madsen), who also happens to be a big wine amateur. Though Miles has nothing to show for himself as a person, he’s able to make a girl interested just by saying all those ridiculously poetic stories about everything wine-y. He’s miserable and anxious all the time, yet Maya seems to be the cure for all his troubles. In the meantime, the sex-filled relationship between Jack and Stephanie is brutally stopped because of the little marriage-related secret that’s finally been revealed. Ironically, even the humiliation and beating don’t stop Jack from trying another one of his cunning tricks on another unsuspecting lady. And who’s going to help him when all his plans are in shambles? Of course no one other than the good ol’ Miles.
In all the naturalism and humanism that permeate the film’s substance, Sideways proves to be a smart, wonderfully-written dark comedy that is not only humorous, but also tremendously realistic. The story might go both ways, and it does at some point, just to arrive at a conclusion that is as heartbreaking as it is actually pleasing. The boys come back from the trip changed, they think differently, and the aspirations that they now have are incomparable. Sideways – with all its charm and subtle pretentiousness – shows that Alexander Payne knows how to create a madly good film with a splendid character-driven narrative, where existential angst is only a man’s world.