Apparently someone thought it will make a great comedy for a new age sensitive, depressed (and balding), "loser" of a literature teacher to take his himbo actor friend for a week of good wine and golf in the Californian wine country before said friend's bachelorhood officially ends. Unfortunately for Miles, Jack of course had other ideas that lean towards excessive physical exercise with a specimen, well any specimen of the opposite sex.
Then again the irrepressible, if infantile Jack serves surprisingly well as the 2-D counterpoint to Miles' more rounded morose and contemplative nature.
Miles Raymond: [while tasting wine] It tastes like the back of a fucking L.A. school bus. Now they probably didn't de-stem, hoping for some semblance of concentration, crushed it up with leaves and mice, and then wound up with this rancid tar and turpentine bullshit. Fuckin' Raid.
Jack: Tastes pretty good to me.
As Miles and Jack tour the vineyards, Miles describes at length the character of different wines they are tasting. At the same time, the choice of wine describes the personality.
Maya: You know, can I ask you a personal question, Miles?
Miles Raymond: Sure.
Maya: Why are you so into Pinot?
Miles Raymond: [laughs softly]
Maya: I mean, it's like a thing with you.
Miles Raymond: [continues laughing softly]
Miles Raymond: Uh, I don't know, I don't know. Um, it's a hard grape to grow, as you know. Right? It's uh, it's thin-skinned, temperamental, ripens early. It's, you know, it's not a survivor like Cabernet, which can just grow anywhere and uh, thrive even when it's neglected. No, Pinot needs constant care and attention. You know? And in fact it can only grow in these really specific, little, tucked away corners of the world. And, and only the most patient and nurturing of growers can do it, really. Only somebody who really takes the time to understand Pinot's potential can then coax it into its fullest expression. Then, I mean, oh its flavors, they're just the most haunting and brilliant and thrilling and subtle and... ancient on the planet.
Yet, Sideways is not all lyrical or romantic, there is a high amount of Jack-induced slapstick that are just so loud and glaring that for me sometimes distracts from the subtle dialogue and anguish of Miles.
Still the script, the animated dialogues between the different characters, the detail that went into portraying Miles' personality made this movie interesting. A watchable comedy that escapes admirably from really descending into one big fat joke.