Book Review: Sideways by Rex Pickett

I have a romantic view of Napa Valley. I always wanted to take a few close friends, maybe my husband, maybe some girlfriends, and drive though Napa Valley, visiting vineyards and pretending to be gauche, listening to music in a convertible with its top down, culminating the day with a picnic somewhere, drinking wine and watching spectacular sunsets. Last year, I actually did have a chance to go to Napa Valley. It didn’t quite live up to my romantic fantasy (though I did get a chance to visit a winery).

That’s pretty much how I feel about Sideways.

When I rented the movie a few months ago, I thought it would be a comedy about two guys touring wine country and learning about life and love. And, in a sense, it is about that, but there’s absolutely nothing romantic about it.

The premise is same for the book and movie. Miles, a writer who has a book making publisher rounds, takes his friend Jack up to wine country to celebrate Jack’s impending marriage. Miles is a morose sort, preferring to be a connoisseur of fine wine rather than focus of the black hole of his depressing life. Jack is simply determined to nail any woman he sees before he gets hitched for good. And he does.

At some point in the movie–I think it was when Jack is boffing some waitress–my hubby turns to me and says, “This is supposed to be funny?”

I’m still trying to figure it out myself. It won an Oscar for best writing for Adapted screenplay, so when I saw the book at a garage sale, I thought, well, maybe the book provides more insight than the movie. So I got it. And read it.

And I thought, this won an Oscar for best writing?!?!

The book opens with Miles going to a wine tasting to wait for Jack. As a pretaste for what the rest of the book turns out to be, Miles swills, whines about his book, depresses himself about women whom he’s sure he’ll never score with, and exchanges good-natured F-bombs with a dentist.

But what really slows the opening scene is the description of every single wine he tastes. I’m not kidding. “I quickly sampled the second Chard, a single-vineyard wine with a better balance of fruit and acidity and subtler oak overtones that imparted a slightly smoky, almost nutty taste.” This is followed a couple paragraphs later with “The second Pinot was a single-vineyard from the nearby storied Rochioli property. It had notes of cardamom and exotic berries, and it pinwheeled around on my palate, deliciously lingering.” Did he get this from the back of a wine brochure? And what’s worse, this is pretty much how it is throughout the entire book. It gets really old fast.

The book version of Miles is far more pretentious and pathetic than his film counterpart. Part of it is due to the writing, I think. Pickett tends to throw in fancy, obscure words (parsimonious, epigone) but he pairs it with pretty bland clichés. It makes Miles comes across as a rude, ostentatious snob. And because it takes at least 20 pages for Jack to show up, I slowly began to feel I was stuck at a very unfunny party. (Even Jack, later on, rags on Miles using such long, esoteric words “Let’s hold off on the ten-dollar words, Bester.”)

At least I had a little sympathy for the Miles in the movie, but because we’re privy to his every thought in the book, it not only makes him a very unreliable narrator, but it’s a pain to slog through his negativity. Of course, Jack isn’t much better. He comes across as a smooth-talking, misogynic creep. I swear, if I read this book if I was single, I probably would’ve sworn off all men. At the point where he tells Miles, “This may come as a shock to you but sometimes…chicks just want to get pounded.” I decided, you know, I think I had enough of this…and proceeded to flip through the rest of the book.

The rest is pretty much the movie. They meet two women, Jack proceeds to sleep with one. She learns he’s getting married and she beats the crap out of him (in the book, she actually has a gun, which was just a tiny bit funny and well-deserved). Miles actually connects with the other woman, somewhat. Until he learns that she was given a thousand dollars to go to bed with him..

Yeah, no one is exactly nice and pure in this book. In the movie it sort of glosses over the characters so at least there’s some redeeming quality in them. Not so in the book. Everyone’s pretty scummy on some level. Even Jack’s fiancée, who you really feel sorry for in the movie. When she dances with Miles at the end, she asks if Jack had sex with anyone. When Miles evades the question, she says, “Well, if he did, tell him we’re even.”


I did a little searching on Amazon to see how reviews for this was. The vast majority seemed to really, really like this book in the way it portrays the two men honestly. You even get to see them try to connect with each other in what would be considered emotionally, as Jack trying to cheer Miles up, trying to get him to move on with his life. And I did get a sense of that when I read the scene when Miles learned that his ex-wife remarried and will be coming to the wedding. It was a pretty powerful scene. But with all the trek before it, it came way too late for me to care. I’m sure that there are other scenes towards the end of the book, but I really don’t know. I just sort of flipped through it.

I did notice that those who gave it negative reviews were turned off by the foul language, the bad writing, and the scummy nature of the characters. Yeah. I gotta agree. This was a real pain to read, and it left me with an urge to take a shower to wash the scumminess off of me. This gets 1 glass of merlot out of 5, because I know that Miles really hates Merlot. He says so. Over and over and over again. So I raise that single glass of Merlot to you, Mr. Miles. You well and truly deserve it.