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Sideways (The Sideways Trilogy #1)

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3.65 of 5 stars 3.65  ·  rating details  ·  3,408 ratings  ·  432 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 st ...more
Paperback, 368 pages
Published October 1st 2004 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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Toby
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
Snotchocheez
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.

Ummmm...no. 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
...more
Lydia
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
Kimberly
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
...more
Casey
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.

Sidewa
...more
Phil Brody
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
Cecilia
May 26, 2007 Cecilia rated it 4 of 5 stars
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
Mags
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
...more
Jonathan
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.
Gina
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
Antof9
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
...more
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
Valarie
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
...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.
Valerie
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...
Eva
Irrelevant, but amusing: It took me far too long to realize that I was listening to this audiobook on shuffle.
Lloyd
Jun 28, 2010 Lloyd rated it 5 of 5 stars
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
...more
Jim Thomsen
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
...more
Margherita Dolcevita
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
Dina
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
...more
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
...more
Kallie
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
...more
Cathy
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
...more
Shannon
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
Steve
Thanks to the movies, I've been introduced to some of my favorite books. While Rex Pickett's Sideways isn't high on that list, I enjoyed it just the same. It isn't a fantastic book and, as many have noted, it is also the rare book that is bested by the movie. It's too long, has some really unnecessary side turns that don't move the plot or provide strong cause for their inclusion, and, while it is a smart observation on humanity and relationships, it is couched in some uneven prose.

Pickett's wri
...more
Audrey
What a fun book to read. I liked the book even better than the movie, and I liked the movie. Lots of mishaps and adventures; interesting and, for the most part, likeable characters(even with their rather serious flaws; some LOL moments; tons of wine info that amazingly isn't boring; and a story that moves quickly. Wow! I really had trouble stopping reading it to go to sleep and at the same time I wanted to stop reading it so I wouldn't come to the end too soon..... Read it.
Benjamin
Jack, actor and director, is about to get married so arranges to spend the week leading up to the big day with his best friend and best man, as yet unpublished writer Miles. They plan to spend the time on a wine-tasting tour of the Californian vineyards, Miles being rather an expert on the subject with a particular love for Pinot. Jack is already comfortably off, and marrying into a wealthy family can only enhance his financial security, whereas Miles is struggling to keep his head above water a ...more
Denis S
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
...more
Eugene  Kisebach
Yes, this is the novel on which the very popular movie was based. I hadn't even known there was a book. Pretty much everyone knows the storyline: Jack is getting married, and he and best buddy Miles head off to wine country for a week of wine-tasting and "fun" before Jack ties the knot. But of course, many adventures and mis-adventures ensue before the week is out. The book is good and I did enjoy it, although it seems a tad more introspective and serious/unhappy than the movie, in particular Pa ...more
Norman Parker
One of the jacket categories of this work of fiction says "Divorced men - fiction". This categorizes me and my motivations of enjoyment for the book. I originally saw this book as a movie, enjoyed it, bought it, watched it a couple more times and wanted to read the book. It captured a reminiscent feeling in me, a wistful mood recognizing how much I miss my marriage.

I love this book, but it is just me. I don't recommend it or divorce to anyone.
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topics  posts  views  last activity   
Eat, Drink, Read: Recipe Pairing- Sideways by Rex Pickett 1 1 May 19, 2015 12:15PM  
Eat, Drink, Read: What a Boar! 1 1 May 19, 2015 12:13PM  
Eat, Drink, Read: Redemption, or lack thereof... 1 1 May 19, 2015 12:12PM  
Eat, Drink, Read: For the Love of Pinot 1 1 May 19, 2015 12:11PM  
Eat, Drink, Read: The Sideways Effect 1 2 May 19, 2015 12:10PM  
Food & Fiction: Food & Wine 4 18 Oct 21, 2014 07:51AM  
Food & Fiction: October Food & Fiction Title! 2 24 Oct 02, 2014 02:08PM  
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Other Books in the Series

The Sideways Trilogy (3 books)
  • Vertical: The Follow-Up to Sideways
  • Sideways 3 Chile
Vertical: The Follow-Up to Sideways Sideways 3 Chile Alien 3 The Road Back Screenwriters Award-winner Set, Collection 2: Sideways, Eternal Sunshine of the Spotless Mind, American Beauty

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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.” 4 likes
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