Miles (Paul Giamatti) and his actor friend, Jack (Thomas Haden Church), are two old college roomies looking to spend quality time with each other before Jack's upcoming nuptials. The pair selects a wine tasting tour through northern California as an activity, which, for wine snob and failed novelist Miles, means revisiting old haunts and familiar faces. Right at the start of their trip, Jack informs his friend that his main goal for the trip is to sample a variety of local women. He quickly falls into lust with a hippie single mother (Sandra Oh, "Last Night"), while Miles, still seething from a divorce, hits it off with her friend (Virginia Madsen, given a role with meat for the first time in years). Despite the diversion, Miles finds that this trip is forcing him to confront his miserable existence, which all his intellect and denial cannot protect him from.
Through his films "Citizen Ruth," "Election," and "About Schmidt," writer/director Alexander Payne has shown a deft hand in detailing the ugly, lurid nature of our everyday lives while finding beauty and solace in the weirdest places. His latest film, "Sideways" (IMDb listing), presents an interesting challenge: Payne has to make an absorbing and funny film about two losers on a wine tasting road trip. I wouldn't wish that plot on my worst enemy.
It truly is a testament to Payne's skill that "Sideways" is a deeply entertaining and intensely honest motion picture. Adapted by Schmidt and his regular writing partner Jim Taylor from the novel by Rex Pickett, "Sideways" is problematic material to begin with, as many of the jokes are centered on wine condescension. I'm sure some people might find jokes about pinot and merlot hilarious, but I've always found that this kind of material screams "specialized audience" in a very ugly way. Fortunately "Sideways" doesn't stop there. It pushes forward to investigate these two characters, and their confounding yet utterly relatable life choices. Payne keeps the camera on Jack and Miles, preferring a humanistic point of view for the film, and not a jokey, elitist vibe that would be the death rattle of a fragile story like this.
Payne loves his fallible characters, from the paint-huffing mother in "Citizen Ruth" to sad sack Schmidt in "About Schmidt." The angle Payne plays on these characters in his features is not one of condescension, but of adoration. "Sideways" is the first of his films to be set outside of his beloved Nebraska, but Payne doesn't lose his love for the average joe. He fills "Sideways" with delightful and realistic working class supporting characters, and extends that invitation to his four leads, who have internal hurdles that are entirely comedic, but also grounded sharply in reality. The ability to find a striking authenticity in comedy is Payne's best attribute, and one that he continues to develop masterfully.
Of course, his eye for casting isn't too shabby either. From the outside, the "Sideways" line-up seems a bit off, what with Giamatti playing his thousandth schlubby character and perennial ham Church suddenly promoted to lead status. However, smart viewers will place their trust in Payne, whose instincts have never disappointed. He smartly casts Church in the cad role (a function the actors plays repeatedly, but very well), and hands Giamatti a character that is familiar to the actor, but shaded differently. Miles is an open wound of a man, drowned in self-loathing and wine (which eventually reveals itself to be a metaphor for the character), and while Giamatti has played this type of role before (many, many times), he does a magnificent job finding the slippery edges to the character, forging his best performance yet. Miles is a heartbreaker, not only because his life is falling apart around him, but because he recognizes the crumbling as it happens. It's gut-wrenching work, often infused with a welcome subtlety that the actor has never displayed before.
"Sideways" rambles on for more than two leisurely hours, but never runs out of gas. This is a tricky film; probably the most complicated material Alexander Payne will ever face, but the filmmaker scores another success by sticking with story, character, and heart. You just can't go wrong with those ingredients, even in a wine tasting film.
Filmfodder Grade: A-