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Sideways: A Novel
The "hilarious, poignant, and intoxicating" wine novel that's the basis for the comedy-drama road movie starring Paul Giamatti and Thomas Haden Church (Jay McInerney).
Sideways is the story of two friends—Miles and Jack—going away together for the last time to steep themselves in everything that makes it good to be young and pinot, putting, and prowling bars. In the week before Jack plans to marry, the pair heads out from Los Angeles to the Santa Ynez wine country. For Jack, the tasting tour is Seven Days to D-Day, his final stretch of freedom. For Miles—who has divorced his wife, is facing an uncertain career and has lost his passion for living—the trip is a weeklong opportunity to evaluate his past, his future and himself.
"A buddy novel in the cinematic vein of Swingers . . . Pickett plays the sex-and-the-single man angle for all its worth here, nodding occasionally at such larger themes as friendship and romance. Call it Nick Hornby lite." — Booklist
"A fresh take . . . credit screenwriter Pickett for coming up with a debut that goes some distance . . . Skillful work about a friendship between two ultimately likeable guys." — Kirkus Reviews
"[A] lively debut . . . Pickett takes his readers on a jolly ride." — Publishers Weekly
Sideways is the story of two friends—Miles and Jack—going away together for the last time to steep themselves in everything that makes it good to be young and pinot, putting, and prowling bars. In the week before Jack plans to marry, the pair heads out from Los Angeles to the Santa Ynez wine country. For Jack, the tasting tour is Seven Days to D-Day, his final stretch of freedom. For Miles—who has divorced his wife, is facing an uncertain career and has lost his passion for living—the trip is a weeklong opportunity to evaluate his past, his future and himself.
"A buddy novel in the cinematic vein of Swingers . . . Pickett plays the sex-and-the-single man angle for all its worth here, nodding occasionally at such larger themes as friendship and romance. Call it Nick Hornby lite." — Booklist
"A fresh take . . . credit screenwriter Pickett for coming up with a debut that goes some distance . . . Skillful work about a friendship between two ultimately likeable guys." — Kirkus Reviews
"[A] lively debut . . . Pickett takes his readers on a jolly ride." — Publishers Weekly
- GenresFiction
365 pages, Kindle Edition
Published April 1, 2010
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Displaying 1 - 4 of 4 reviews
May 16, 2025
I saw (and loved) the movie first and picked up the book almost twenty years later. The movie, and the book, have such a charm that I almost regret being a tee-totaler because the world of wine-tasting is brought out in all its glory.
Of course, it's also a bachelor story, two old friends in their 30's. One an actor and a hedonist, the other a struggling writer who is much more a hedonist than he's willing to admit. It's a road trip story. Miles and Jack, two old friends, going out for one last week of wine and chasing women before Jack ties the knot.
A part of me actually likes the movie better just because the central California setting is really brought to life and though both versions are bachelor romps, I thought the book went further than I wanted to into the head of Miles and the base motivation of Jack. I actually didn't think as much of the characters because a lot of the emotions and urges were generic and simply overdone.
I still enjoyed it quite a bit and Rex Pickett has a way with words and with describing settings. I'm not intrigued enough to read the sequels, at least not yet. To me this is a good stand-alone story, I don't care so much to read about another romp.
Of course, it's also a bachelor story, two old friends in their 30's. One an actor and a hedonist, the other a struggling writer who is much more a hedonist than he's willing to admit. It's a road trip story. Miles and Jack, two old friends, going out for one last week of wine and chasing women before Jack ties the knot.
A part of me actually likes the movie better just because the central California setting is really brought to life and though both versions are bachelor romps, I thought the book went further than I wanted to into the head of Miles and the base motivation of Jack. I actually didn't think as much of the characters because a lot of the emotions and urges were generic and simply overdone.
I still enjoyed it quite a bit and Rex Pickett has a way with words and with describing settings. I'm not intrigued enough to read the sequels, at least not yet. To me this is a good stand-alone story, I don't care so much to read about another romp.
September 20, 2026
train wreck
This was uncomfortable to read and I gave it two stars instead of one for some scenes that made me laugh out loud. But there’s nothing remotely redeeming in any of the main characters and the ending was disappointing. No growth, no character development. It was two insecure drunk people trying to justify themselves. Skip it.
This was uncomfortable to read and I gave it two stars instead of one for some scenes that made me laugh out loud. But there’s nothing remotely redeeming in any of the main characters and the ending was disappointing. No growth, no character development. It was two insecure drunk people trying to justify themselves. Skip it.
June 21, 2026
Loved the film and the book feels just as breezy with the characters fleshed out and amped up in their activities. A wonderful, ironic look at how despicable men are. Miles is a brilliantly un-self-aware creation that can't help but place himself at the centre of everything.
September 2, 2026
The Hits Just Keep Coming
This book taught me a lot about wine. We've all been in that place where it seems life is leaving you behind and your friends and family seem to be distant. I can relate but it's not heavy there are enough funny moments and banter to get you through.
This book taught me a lot about wine. We've all been in that place where it seems life is leaving you behind and your friends and family seem to be distant. I can relate but it's not heavy there are enough funny moments and banter to get you through.
Displaying 1 - 4 of 4 reviews