Book Review: “Sideways” by Rex Pickett, 2004, published by St. Martin’s Press

Miles, a struggling novelist, is divorced and depressed, while his best buddy, Jack, is a moderately successful actor who is about to get married. Together they embark on a weeklong wine-tasting trip in Rex Pickett’s raucous and hilarious debut novel, “Sideways.”

For Jack, the trip is his last chance to enjoy his freedom. For Miles, it’s a much-needed respite from his dismal life. Unemployed and unpublished, he steals money from his own mother for the trip. The two have different goals for the weekend. Jack wants a last-ditch romp with willing women, while Miles, a wine connoisseur, looks forward to getting blissfully sideways.

The story takes us from Los Angeles to the luscious vineyards of Santa Ynez in southern California. True to the road-trip trope, Miles and Jack encounter numerous misadventures, including a boar-hunting expedition gone wrong and Miles’s suspenseful extraction of Jack’s wallet from the bedroom of a married couple who were getting it on. However, their biggest misadventure is romancing two local women. Miles falls for Maya, who has the makings of his soul mate, but Jack complicates things by fooling around with Maya’s friend, Terra.

The Lovable Loser

Miles is funny and intelligent, the kind of guy who uses words like ersatz and zaftig. His appreciation for wine is infectious, his knowledge impressive. Here’s how he describes a bottle of La Tache: “The wine had three distinct acts, like any well-written story. Act one revealed a tart, almost perfumed fruit unlike any pinot noir I’d ever tasted. Then somewhere in the middle, I could detect black truffles and rose petals…then act three, it kept calling out caressingly as it went down, like a voice echoing plaintively in a tunnel, while we lamented in its absence.” Somebody get me a glass of pinot noir, please!

Although Miles is a failure as a writer and very bitter about his divorce, he’s a good friend to Jack. He tries his best to hold Jack to the straight and narrow. In short, Miles is a loser I can root for.

The relationship between Miles and Jack is one of the best things in this novel. They bicker and fight, but in the end, they perform incredible deeds (I won’t reveal) that prove their loyalty to each other.

“Sideways”: The Movie

I read this book because I love Alexander Payne’s movie, also called “Sideways,” starring Paul Giamatti as Miles and Thomas Haden Church as Jack. It’s one of those rare movies that successfully captured the essence of the book. Payne and Jim Taylor won the Oscar for Best Adapted Screenplay.

This past weekend, my family visited Napa Valley for our wedding anniversary celebration. I couldn’t help but think of Miles and Jack as we drove through winding roads, picturesque vineyards unfurling around us.

“Sideways” is more than just a road-trip story—it’s a celebration of friendships, and yes, wines. And so, I lift my proverbial glass and offer a toast to both the movie and the novel!