A number of years ago (18 to be exact), Sideways the movie, made it’s debut. While it was a strong effort, winning a number of awards including, oddly enough, Best Writing – Adapting a Screenplay (more on why that’s odd in a moment) in my mind it just fell short. Having not even read the book at that point, I found Giamatti’s portrayal of the Miles character to be whiny to the point of nauseum (and still do) Sure, the Merlot scene is hilarious and there are a few others, but over all, he portrayed that life is a glass completely empty. Which was subsequently crushed and used to lacerate an artery. It wore thin…

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So when the opportunity to read the book came up, I was understandably hesitant (but in the back of my mind that phrase “but you should read the book, it’s so much better” kept egging me on. So I finally relented and dove in, and I’m so glad that I did. From the very start, the character of Miles shines in a completely different light. Is he still neurotic and grating? Very much so, but in a much more relatable way. He becomes the character that most of us probably know and may even be friends with. A far cry from the one in the movie that you want to put a bullet in. In the same way that Miles improves, so does Jack. The book description of Jack sounds much more like a ladies man that’s capable of getting any woman he wants. Unlike Thomas Hayden Church, who no offense, I probably wouldn’t cast in the role of McDreamy on Grey’s Anatomy. The primary supporting cast, who ironically enough includes Sandra Oh as Terra (who’s called Stephanie in the movie) starred in Grey’s Anatomy a few years after this. Virginia Madsen plays the role of Maya. Both of these ladies do a stellar job and their parts stick very closely to those found in the book.


This brings us to Rex Pickett, the author of the 3 Sideways books (and the just recently released The Archivist) It’s easy to see why this book was adapted into a screenplay. The opportunity to showcase engaging characters, the potential for stunning cinematography and the clear thrill of constant conflicts and resolution, that literally jump from the pages make this a screenwriters wet dream (oops..sorry). Unlike opportunities missed in the movie, Pickett connects the dots throughout the entire book. The Jack and Miles characters are clearly defined and you somehow have compassion for them, even throughout their poor and self absorbed decisions, you find yourself rooting for them. This really is a book that brings you in and takes you along for the completely dysfunctional ride. Without giving too much away, the story line and character development for Vertical (the 2nd book in the series) was even more enjoyable. But you’ll have to wait 2 weeks for my thoughts on that one

This is the first of 3 reviews of the Sideways trilogy. Coming up next is Vertical, a cross country journey of madness with Miles, Jack, Miles mother and a personal care nurse. Following that will be Sideways 3 – Chile, which I have just begun. Be sure to stop in every Friday for the weekly Booze Press Bookshelf or Booze Theater review…We won’t steer ya wrong. Cheers!

This book receives 4 out of 5 glasses. Order here: Sideways