With the news that director Alexander Payne and actor Paul Giamatti are reuniting for their second go-around with, per Variety, The Holdovers, now is as good a time as any to return to 2004 and re-visit their first collaboration together. Sideways was a surprise hit that few were expecting, and like most punches, it’s the ones you don’t see coming that are the ones that knock you out.
It’s hard to follow up a film like About Schmidt, but not only did Payne match the greatness of his sophomore effort, he exceeded it and made one of the most underrated masterpieces of the early 2000s. This article will specifically look at the complex relationship between the characters portrayed brilliantly by Giamatti and Thomas Haden Church.
A Complicated Friendship
Searchlight Pictures
The film follows Miles (Giamatti) and Jack (Haden Church) as they plan to spend Jack’s final week as a bachelor in Santa Ynez Valley wine country, eating, drinking, and playing golf. Miles is an introverted wine expert who teaches middle school English, and Jack is an uninhibited former soap opera star with a fledgling acting career and a raging libido. They spend the week shifting back and forth between being insufferable, self-obsessed idiots and wretched, miserable dicks. There are moments where you cringe and wonder how these two could stand to be around each other, and it is in these moments that this film excels. It captures a side of friendship most buddy comedies tend to stay away from. It’s not always a hopeful “us against the world” proposition. It can be vulgar and melancholy, and it’s these moments Payne captures so eloquently.
The best scene of the film is when Jack shows up at the hotel naked in the middle of the night and confesses that he ran a couple of miles across the valley after getting caught sleeping with a married woman. He breaks down and tells Miles that he left his wallet, which contained his wedding rings. Miles laughs in his face until he sees how hurt he is by the prospect of losing his fiancée, and Jack begs Miles to help him retrieve the rings from the house. They drive to the place where Miles breaks in while the husband engages in some pretty aggressive sex with his wife just hours after cheating. He snatches the wallet off the dresser and gets chased by the naked husband down the street.
Moments like these give these characters the only redeemable quality they have. They both understand very little outside of what being a good friend means. Friendship isn’t always about trying to fix someone. It’s about accepting someone for who they are and being there for them to help pick up the pieces of their broken selves. These two are the only people who comprehend how broken the other is, even if they don’t see it.
Differences Between Miles and Jack
Miles is the type of person that pours 100% of himself into the things he loves, only to have it given back to him. When this happens, he becomes self-destructive and wants to crawl into a hole. Whether it’s his manuscript, his failed marriage, or the “ideal” bachelor party weekend he planned around his interests, it’s a constant bid for control, and when he doesn’t get it, he throws a temper tantrum, and it leaves him in despair. He constantly broods over whether he’s good enough to be loved or talented enough to be the artist he wants to be; instead of taking the necessary steps to figure it out, he opts to be a sad, pathetic bastard and crawls into a bottle. He is the coward most of us can regrettably be sometimes.
Jack is the opposite. He is brave enough to try everything, but he’s not intelligent enough to think about whether or not he should. He can’t commit any part of himself to anything, as evidenced by the fact that he spends the whole week cheating on his fiancée and constantly changing his mind about whether he even wants to marry her in the first place. He tricks himself into thinking he is cooler than he is and is always trying to impress Miles. Miles sees through this and calls him out on it every chance he gets. It’s what Jack needs, and he appreciates Miles for it because you can tell he genuinely respects his intellect even though he despises his incessant negativity.
This is the genius of Sideways. Every decision these characters make on their own is a flawed, pathetic attempt to validate their insecurities. Still, the advice they give to each other that they repeatedly ignore is the medicine they need to cure themselves. Sideways is more than just “that wine movie.” It’s a hilarious glimpse into middle-aged loneliness that sticks with you even if you’re not approaching middle-age. It helped establish Giamatti as one of the finest actors of his generation, and his performance in this film is arguably the most significant snub in Oscars history. The sensitivity Giamatti approaches this character with is the same delicacy that a master vinter approaches winemaking. Like Miles says,” Only somebody who really takes the time to understand pinot’s potential can then coax it into its fullest expression."
