Sideways by Rex Pickett – a review

Rex Pickett’s 2004 novel Sideways will probably be best known as the source for the critically successful film starring Paul Giamatti. The success of the film possibly overshadowed the novel, which is a shame because it’s a charming little tale that details two men on a road trip dealing with their respective mid-life crises. Pickett, a Hollywood writer and screenwriter, creates a terribly sad portrayal in the main character Miles Raymond. A wine-guzzling alcoholic who’s broke, divorced and living in the shadow of his disastrous marriage. Miles is best friends with Jack Cole, an aging b-movie lothario who is approaching his impending marriage with self-destructive fear and apprehension.

The story takes place in the Saint Ynez wine country. Miles and Jack decide to go for a week throughout the wine country, drinking obscenely expensive wine while playing golf. For Jack it’s one last hurrah before getting married; for Miles it’s a way to escape his failing career, depressing love life and ruinous financial situation. During the trip, Jack confronts his deeply equivocal feelings about marriage and his fiancée, and tries to obscure his fears by bedding loose women. For Miles, Jack’s tomcatting is frustrating because he’s still nursing wounds from a devastating divorce, and sees his friend’s foolish behavior as immature and offensive.

Pickett’s strongest gifts are his facility with dialogue and his cutting-sharp wit. While the characters all have a barbed sense of humor, he doesn’t rely on cheap, gimmicky snarkiness to mask true feelings (a crime that Diabo Cody sometimes commits). Jack and Miles are deeply damaged men, who cannot seem to understand how they can free themselves from their mire, but they still care, mostly about each other. The friendship between the two men is beautiful: it’s honest, funny and sad. Pickett never lets either Miles or Jack off the hook: they both contribute mightily to their mishaps (and they do have a few), but because underneath all the neuroses they’re basically good guys, the reader is left rooting for them.

Sideways works because it’s a buddy comedy of a different sort: a sad, wistful, thinking man’s buddy comedy, where the heroes aren’t comics throwing off one-liners, while the babes throw themselves at them. Instead Pickett draws a very real portrait of two men who are struggling within themselves to somehow slough off their imaginary obstacles to find some semblance of happiness. It’s not an inspirational novel, nor is it particularly uplifting – yet in the end, Pickett’s done an extremely satisfying job in inviting his readers into the lives of these two flawed, failing, yet wonderful men.

Click here to buy Sideways on


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Filed under Book, Comedy, movie

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