Sideways (2004)

The more I drank, the more I liked what it made me think about

Sideways offers a middle ground between Election and About Schmidt: it is a fiercely cynical black comedy and light drama, but tempered with just a bit of sentimentality and optimism. Election sent Matthew Broderick to pathetic oblivion as a speck in New York City; Sideways lets Paul Giamatti knock on Virginia Madsen’s door as the screen cuts to black. Giamatti’s Miles offers not for the first or last time in Payne’s filmography a pathetic high school teacher that serves as a vessel for Payne’s views on deferred dreams and wasted potential. But Miles is more “thin-skinned and temperamental” than Broderick’s McAllister (and perhaps less so than The Holdovers’ Paul Hunnam, also played by Giamatti). Payne offers with both sadness and hope the prospect of his protagonist aging like a fine wine so long as he opens himself to the world before he completely spoils like a ’61 Cheval Blanc. It’s the perfect balance in tones for Payne, and the result is his very best film to date.

Sideways follows a bachelor party road trip through California wine country to celebrate the upcoming nuptials of D-list actor Jack (Thomas Hayden Church), hosted by his college roommate and best man, oenophile Miles. Both are seemingly normal middle-class dudes on the surface, but each is crippled with an addiction that results in them ending every night sideways: Miles is a barely-functioning alcoholic, and Jack is a relentless sex addict hoping for one last wild weekend before the ball and chain. They cross paths with Stephanie (Sandra Oh), a feisty wine pourer with connections in the wine sphere, and Maya (Madsen), a smart and sweet waitress with a soft spot for overthinking schleps like Miles.

All four of the leads are sensational; funny and sad and soft and sexy as each scenario requires. Giamatti in particular makes a case as the funniest actor on the planet; his “I am not drinking any fucking merlot!” is up there with George Costanza’s “these pretzels are making me thirsty!” as one of my favorite line deliveries ever.

Despite Payne’s terrific writing, the film’s construction and pace is a bit slack. It’s not as turgid as the middle of About Schmidt, but it takes its time with montage and vignettes. The editing and timing lacks the spitfire punch of Election, and the score is snoozer that imposes itself a bit too strongly. But Payne still has a knack for toggling between the bleak and the hilarious on a dime, and filling his little asides with personality to build distinct character portraits and emotional textures. Sideways also shows a deep passion and reverence for the wine itself, capturing a hundred red and white shades glowing in the dusty light, never holding back on the intoxicating effect wine has on discerning palates. Sumptuous wine porn.

I first saw this film when I was about 19 years old, which is absolutely too young for the subject matter to fully resonate, but I’m glad I did: Its dark-but-honest insights on accepting yourself as an unremarkable person while still dreaming for more really stuck with me. Rewatching feels like visiting old friends, even if they happen to be a little bit pathetic. I might be overrating it a bit as a result, but damn if Sideways isn’t one of my favorite comedy-drama films of the 21st century.

Is It Good?

Exceptionally Good (7/8)

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