Directed by Alexander Payne, starring: Paul Giamatti (Miles), Thomas Hayden Church (Jack), Virginia Madsen (Maya), Sandra Oh (Stephanie), 108 minutes, 2004.
It is rumoured that Sideways caused the merlot sales to plummet and the pinot noir sales to soar in the Okanagan wine industry. Urban myth or not this is a very popular movie not least because it combines sunshine, wine and romance. People like the movie or hate it. There's a lot not to like.
First of all the male leads: Miles is a whiney, self-absorbed schlep of a guy. He lies and even steals money from his mother. He is divorced but still hopelessly hooked on the relationship with his former wife. He sees himself as a failed novelist and is anxiously awaiting news from a publisher. He fancies himself a wine connoisseur and the main device of the story is a road trip that Miles takes Jack on through California wine country as a wedding gift for Jack who is to be married the next week. Jack on the other hand is fun loving and adventurous but a compulsive womanizer, emotionally shallow and dependent.
Stephanie is the mirror image for Jack; fun loving, lively, rides a motorcycle and is ready for romance. Maya is serious like Miles but independent and well differentiated. In one telling scene Miles talks about why he likes pinot noir. It is because it is "thin skinned and difficult to cultivate". We understand that he is awkwardly describing himself. Maya, on the other hand describes wine making in quite personal terms. She wonders about the people who have cultivated the crop and describes the life that exists in a bottle of wine. She wonders about the mixture of sun, soil and grape that tastes different on the day it is opened than on any other day, unless it suddenly and irrevocably declines before it is opened. This prescient remark describes their relationship, which almost terminates before it is uncorked. The men and the women seem mismatched.
Both of the men are brought up short. Jack thinks he may have fallen in love with Stephanie but when that relationship goes south because of Jack's duplicity he becomes lost and despairing of the potential demise of his own wedding. He literally and figuratively bottoms out in a farcical scene in which having turned from Stephanie to a one-night stand with a waitress in the bar, he has to run for his life, naked and exposed. However, Jack remains the same hopeless puppy dog to the end. Miles, though, experiences a turn that just might be repentance and redemption.
The fact that these are amusing but not likeable men heightens the theme of redemption. These are very ordinary, very flawed men in need of turning around, being redeemed. Apparently, that's how redemption works; even for liars, even for thieves, even for the emotionally stunted. (Whew!)
This is not just a buddy/road movie. Miles does not suddenly move from sideways to upright. His novel doesn't get published, his ex-wife does not return and Maya does not relent and proclaim her love. In that sense it is an ironic tale. Miles is able to face a threshold and cross over it. Not so much a happy resolution in which truth, true love, the true path is found but a new courage to continue the journey. Redemption enough?