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Sideways (The Sideways Trilogy #1)

3.67  ·  Rating Details  ·  3,910 Ratings  ·  469 Reviews
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 single: 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 stre ...more
ebook, 368 pages
Published April 1st 2010 by St. Martin's Griffin (first published June 2004)
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Community Reviews

(showing 1-30 of 3,000)
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May 07, 2008 Toby rated it did not like it  ·  review of another edition
I’m usually not fooled into buying novels by movies. In this case, however, I liked the movie and a spot-check of the novel made me think I might actually enjoy it. Well, I think I got about 20 pages in before I cast it aside in disgust. Even if I could overlook the pretentious wine-talk masquerading as prose (paraphrase: “I took a drink of the Pinot and my palate was massaged by the subtle blackberry highlights and the nutty finish. It turns out that none of the adjectives I and my pretentious ...more
Jan 19, 2011 Kimberly rated it it was amazing  ·  review of another edition
Granted, I hated this movie before reading the book. In fact, as I can attest alongside other females in my friend group - we all hated it. The men? Loved it. Of course, I was never one to cheer for a douchebag protagonist that can't keep his fly zippered.

That was until I encountered the book. Here, Rex's text makes sense - creating a fuller life of Miles and That Other Asshole that the movie could not do justice. Far from being a douchey wino's primer on what wines to drink (ahem... the Merlot
When "Sideways" came out a few years ago, I remembered promising myself to read the book; given that I thought the movie was generally pretty interesting, and that it (rather, Alexander Payne) won an Oscar for best adapted screenplay, I figured it would be worth taking a look at the source material. I wouldn't say that Rex Pickett's oenophilic buddy novel was terrible or anything, but I really don't see how Alexander Payne saw the kernel of a great story in this vapid, moribund homage
Oct 07, 2012 Lydia rated it it was amazing  ·  review of another edition
I have read this book many times. Six? I have never read a book that is so perfectly written, in terms of proper word usage. The first time was a little frustrating because he uses so many obscure words, however appropriate. I resolved to keeping the dictionary by my side. By the third time I was so in love with Rex Pickett as a writer I had to read it again and again. He is a language master. Every word is so absolutely perfect and specific to exactly what he means to say. It is the most fun I' ...more
May 26, 2007 Cecilia rated it really liked it  ·  review of another edition
Recommends it for: WIne Lover
I really loved this book. I liked the movie, but as some one who knows a little about wine I had a real problem with the movie's reference to Central California as Wine Country. The book made it really clear that Santa Barbara was the poor man’s wine country. The book also did a good job to giving some insight to California’s wine culture and how the tasting bars are becoming the local pubs The other thing the book did was to reference real California wines and wineries. The minute I read that t ...more
Phil Brody
Jan 21, 2012 Phil Brody rated it it was amazing  ·  review of another edition
Like many, I loved the movie Sideways. However, like many, I never got around to reading the novel by Rex Pickett that it was based on -- that is, until last month. Reading Sideways was like catching up with an old friend. While I would have loved to have read the book first, I do feel my familiarity with the characters (from the movie) added to my reading experience. I found myself excited to spend more time with Miles, Jack, Maya, and Stephanie, and was delighted to dive deeper into their pers ...more
Let's get this out of the way up front: the movie was much better than the book. Objectively, Sideways deserves only two stars, and that's really pushing it. I mean, this is a book that contains this sentence: "Maudlin classic rock for the 70's saccharined [sic] the emptiness with its plangent strains, further sickening me." Seriously, come on. However, for completely subjective reasons that really have nothing to do with the book, I'm giving it three stars. I'm just that kind of reviewer.

Asghar Abbas
May 06, 2016 Asghar Abbas rated it it was amazing  ·  review of another edition

Comradeship and the Road.




Read this.
Oct 07, 2015 Mags rated it did not like it  ·  review of another edition
Shelves: loathed
When I was younger, I vowed to myself that I will finish every book I will ever start, to see every novel until the end. Now, I've learned myself a new lesson: if you don't like it, don't read it. Continuing to pursue something that you're growing to hate will dampen your spirits. It's not going to get any better.

This one-star rating is based on the first 9 pages that I've read. I know, it's not much to go on, so I will tell you to not trust that rating. Trust me when I say, though, that if a no
Oct 04, 2007 Jonathan rated it it was amazing  ·  review of another edition
Sometimes I'm glad that when I've seen a film before I've read the book. I'm not sure I would have appreciated the film as much had I read this book, which was fantastic, beforehand. I think Alexander Payne made some good choices in what to keep and what to cut in the film, but there were some significant differences. The characters were far more multi-dimensional in the book -- neither was quite as pathetic as in the film, and their friendship was more interesting, and more believable.
Jul 03, 2015 Paul rated it did not like it  ·  review of another edition
Recommends it for: Nobody. Nobody at all.
Here we are presented with something new: a book with the capacity to ruin a movie.

This is a remarkably poorly-written book, and on the basis of the evidence presented here, Rex Pickett is an appallingly bad writer. I'm not engaging in hyperbole: I was truly shocked at the execrable quality of the writing. To say that the movie script is a more accomplished work of literature doesn't begin to capture the indefatigable badness of this book. There is some indication that this book was published on
Denis S
May 29, 2014 Denis S rated it it was amazing  ·  review of another edition
This is a delightful book, well written, funny, sweet, earthy, full of life and meaning. Apparently some reviewers couldn't get past the "wine speak", feeling it pretentious and elitist, and thereby, in my opinion, not getting it.

The combination and interaction of the two main characters, Miles and Jack, is magical. Add to that the scenic wine country where all this takes place (is there anywhere more wonderful?) and this book simply registers with me on nearly every level.

These characters are
Jun 28, 2010 Lloyd rated it it was amazing  ·  review of another edition
Shelves: 2000s
At 350+ pages, this might be the longest book I've read within a 24-hour period. And despite being home sick not really wanting to do anything besides lie in bed and read, I really think I'd have spent whatever time I had today on this amazing work.

I had a friend once that was absolutely enamoured with the story of Stpehen King's "The Shining". He loved the book, he loved the movie, he just couldn't get enough of it. Finally, I think I know how he feels about it, because that's how I feel about
Gina Rose
Feb 02, 2013 Gina Rose rated it really liked it  ·  review of another edition
Jack and I wound our way up the US-101 North towards Buelleton. The freeway ribboned before us and my mind again began to wander and curl itself around the endless and decadent tasting possibilites that lay before us in what I had described to my agent Evelyn on that phone earlier that day as "the poor man's wine country." Jack's mind seemed preoccupied as well; he gazed longingly and vacantly into the gray clouds that loomed before us. I wondered for a brief moment if he was absorbed in thought ...more
So. . .I really liked this book! I think it was Miles I liked best. I have to say that I just love the way he talks :) I'm a sucker for a smarty-pants with a good vocabulary. However, don't be surprised -- this book is really coarse. I couldn't think of another word to describe it than that -- I think it's most apt. The way sex is described and the use of the "F" word are definitely in your face, but it's still a fascinating story.

The idea of one last fling before a wedding is nothing new, and t
Sue Bridehead (A Pseudonym)
Alexander Payne and Jim Taylor made some very, very wise decisions when adapting this to film. Some of the most meaningful moments of "Sideways" the movie are not in "Sideways" the book (Miles touching Maya on the back of the neck outside her door; Maya's monologue about grapes; Maya's career aspirations; Maya's very kind voicemail message to Miles at the end of the movie, wherein we finally learn the topic of his failed novel - a writing choice which redeems Miles as a character worthy of the l ...more
Aug 11, 2013 Valarie rated it liked it  ·  review of another edition
Shelves: audiobooks
Choosing the number of stars on this one was hard. It's basically a well written train wreck! The trouble that Miles and Jack get into is absurd and outlandish but....I could not stop reading (or listening rather, to the audiobook). I can't say that I personally related to either of them but at the same time I couldn't give up on it. I had to find out how it ended!

Final thoughts:
I have a rekindled interest in wine.
I am not at all surprised this is now a movie. That said, I'm not particularly i
Oct 10, 2015 Rob rated it really liked it  ·  review of another edition
Shelves: comic-fiction, usa, 2015
Like most of the readers of this comic novel with its wine-themed middle-age crisis extrovert/introvert division, I saw the film first. Which means it's actually physically impossible not to imagine these guys as Paul Giamatti and Thomas Haden Church. I've tried. You get 1 page away with your new vision and then you lose it. This is both good news and bad news. The good news is that the work by these two actors was so spot-on that it redeemed some of the casual navel-gazing misogyny of the novel ...more
John Mitchell
Oh dear. This is a great story but the worst writing ever. Who would describe a waitress as, "Her compulsory cheerfulness sounded psychopharmacologically tuned to a constant even pitch."? Utter nonsense. This book is written the way a computer would write. A bad computer with access to a thesaurus. Watch the movie but don't waste your time with this appalling prose that tries to impress with words that no one cares about.
Sep 08, 2009 Valerie rated it really liked it  ·  review of another edition
This book was slightly misogynistic or maybe I'm just completely unaware of what guys are really thinking! That being said, it was a fun read - very easy to get fed up with the main characters but you definitely wanted to know what was going to happen next. Worth reading just for the 'I'm not drinking fucking merlot!" line...
Charles Clymer
When the film "Sideways" was released in 2004, it became a sleeper hit, launching from initial arthouse status to worldwide acclaim. And for good reasons: the writing and acting are superb, the wine theme is interesting enough to lure in oenophiles without being inaccessible for folks who know nothing about "drinking grape", and the interplay between Paul Giamatti and Thomas Hayden Church is flat-out fantastic. Why a sequel was never made is beyond me.

As conventional wisdom goes, a film adaptati
Aug 13, 2011 Eva rated it it was ok  ·  review of another edition
Irrelevant, but amusing: It took me far too long to realize that I was listening to this audiobook on shuffle.
Jim Thomsen
Aug 14, 2010 Jim Thomsen rated it really liked it  ·  review of another edition
A triumph of story over storytelling. I'll admit my perspective may be clouded by my fond memories of a perfect movie, but I think the novel could have used some of the movie scene-oriented storytelling technique. Instead, Rex Pickett stuffs his novel with superfluous connective tissue, making me slog through needless descriptions of hotel rooms and highway strolls and seemingly everything else, significant or not, one might encounter on a road trip.

It's an annoyance, but not a fatal one, becau
Margherita Dolcevita
Nov 14, 2010 Margherita Dolcevita rated it it was amazing  ·  review of another edition
Shelves: lad-lit
Un bellissimo romanzo on the road in cui il vino accompagna due uomini accomunati da una bellissima e prettamente maschile amicizia (noi donne un'amicizia così mi sa che ce la possiamo solo sognare, ahimè). Il vino è un pretesto, vengono spese alcune parole per descriverlo e degustarlo, in realtà il vino è una metafora per la vita e per l'uomo. E si ride anche tanto, nonostante le molteplici (ma non inutili) volgarità. Il film è assolutamente all'altezza: ne conserva lo spirito e proprio per que ...more
May 07, 2009 Dina rated it liked it  ·  review of another edition
Having been a huge fan of this movie, I thought for certain that the book would be terrific as well. I was 75% right, as in, 75% of the book was just as good as the movie, if not a little better and 25% of the book left me asking 'Really?'

Rex Pickett is a screen writer and this is his first novel, so the back of the book informs me. This fact seems to be quite evident in his writing; details that are less than inspired and adjectives and verbs sounding more like stage directions. It's not that t
Greg Branch
The plot here is well known. A shallow yet charming and handsome soon to be married actor travels to wine country for a week pre-wedding getaway to Santa Barbara's wine country with a depressed, alcoholic, want-to-be author friend. The problems that ensue all relate back to the characters internal flaws.

I saw the movie before reading the book which is usually the preferred order for me. Here, I think it really didn't matter since (unlike other reviewers) I found that the book did not give the c
Feb 09, 2010 Kallie rated it really liked it  ·  review of another edition
I'm one of the those people who like to see movies based on books. Don't know why, I'm always disappointed due to the film leaving so much out. I understand the why of it but that doesn't mean I have to like it.
I was laughing from beginning to end. I had my own envisions (?) for what the characters looked like, their personalities and how the scenarios played out. Of course there's two underlying stories with each of the main characters and I found myself feeling really bad for Miles. I wanted
Jun 15, 2009 Cathy rated it it was ok  ·  review of another edition
I loved the movie, and was eager to read the book ... and, it turns out that the book is a really, really good film proposal. Pickett's prose is clunky and awkward, and he packs the book with Miles' detailed opinions about particular wineries and motels, which is just not that interesting. The strong points of the novel are the unlikely friendship between the guys, and the boozy mishaps they encounter over their weeklong debauch -- and these are the elements that made the film so good.

Because P
Matthew Sanders
This is an intriguing idea with overall poor execution. There is so much unneeded description filler/over the top descriptions that it detracts from enjoying the book. I've never read a book up to this point where so many characters laugh themselves to tears over things which would arguably solicit a chuckle from a normal person. It is one of the rare occasions in which the movie was actually more enjoyable than the source material because it trimmed a lot of unnecessary fat/ridiculous scenes an ...more
Jan 26, 2008 Shannon rated it it was amazing  ·  review of another edition
Love the movie, love the book, love the story, love the characters. I just love everything about Sideways to tell you the truth. If you saw the movie and didn't like it, you probably won't like the book. I know, very surprising right? It's basically about this writer who can't get published who's depressed taking his best friend who's about to get married on the wine tour across California. And the guy who's about to get married just wants to get some action before he ties the knot. It's a lot a ...more
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topics  posts  views  last activity   
Eat, Drink, Read: Recipe Pairing- Sideways by Rex Pickett 1 3 May 19, 2015 12:15PM  
Eat, Drink, Read: What a Boar! 1 2 May 19, 2015 12:13PM  
Eat, Drink, Read: Redemption, or lack thereof... 1 2 May 19, 2015 12:12PM  
Eat, Drink, Read: For the Love of Pinot 1 3 May 19, 2015 12:11PM  
Eat, Drink, Read: The Sideways Effect 1 3 May 19, 2015 12:10PM  
Food & Fiction: Food & Wine 4 19 Oct 21, 2014 07:51AM  
Food & Fiction: October Food & Fiction Title! 2 27 Oct 02, 2014 02:08PM  
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Other Books in the Series

The Sideways Trilogy (3 books)
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“You're such a cheater. The best wood in your golf bag is your pencil!” 6 likes
“Pinot Noir country. My grape. The one varietal that truly enchants me, both stills and steals my heart with its elusive loveliness and false promises of transcendence. I loved her, and I would continue to follow her siren call until my wallet--or liver, whichever came first--gave out.” 5 likes
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