Sideways

by Rex Pickett

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This 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 stretch of freedom. For Miles -- who has divorced his wife, is facing an uncertain career and has lost his passion for living show more - the trip is a weeklong opportunity to evaluate his past, his future and himself. show less

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28 reviews
There is something distinct about the literature from Los Angeles and to an extent California as a whole that's as distinct as the people who live there (here). On the one hand you have beautiful beaches, Hollywood, great restaurants, incredible vineyards, a wide variety of clubs, bars, the nightlife, some of the best universities in the US of A, along with museums, historical and cultural landmarks, and a quality of life that, along with incredibly agreeable weather, is tough to beat.

And here comes the 'but'.

But there's also the artificiality of it all. The manicured and manufactured lawns with their counterpart fingernails and smiles. The dirty and at times even disgusting hovel/city that is Hollywood. How everything, without show more exception up to and including those great universities, is ridiculously expensive. The waters of the beaches are as polluted as the desperate and frustrated souls trying to make a name for themselves in a city that wants them for a minute, if that, but discards you for a lifetime the second it thinks it owns you...also parking's a real problem.

It's a gentle river with piranhas devouring each other beneath the surface. A Hollywood premiere where the stars don't know the waiters spit in their drinks because their screenplay was rejected for the umpteenth time. It's home. And while I wasn't born in LA, since the age of four or so it's been mine. I've hated to love it and vice versa all the way below and beyond the nadir when I realized how much of me was and is wrapped up here. And I have to wonder if Kafka felt this way about his Prague.

Rex Pickett really understands the California state of mind, at least so much as it's presented in his novel 'Sideways'. The relaxed and the casual saddled from being too much so by the ever-presence of artificiality and neuroses. And those on the outskirts of LA and California who just can't seem to figure it at all, if they even acknowledge it.

The protagonist Miles (through whose perspective we get the story, a great call on Pickett's part as Miles is one of the most fully realized first person narrators I've come across, I'd almost call him a grown-up, slightly matured but just as embittered Holden Caufield) is this in a nutshell. He's very intelligent but unfortunately the depression he's going through along with the frustrations of his life (stunted authorial aspirations, a wreck of a former marriage) poison that intelligence whilst offering the rare glimmer of what once was and what could be again. He's a witty bastard, Miles, no doubt. But there are certain parts of the book wherein the 'bastard' is emphasized. Sometimes over the course of it you feel sad that someone this troubled is alone but then, through some of his actions, you see that maybe some of that isolation is well deserved (his stealing money from his mother, his elitism, his snobbery, his narcissistic and obsessive self-loathing, and on and on).

But, and this is where I differ with some of my fellow reviewers, I feel all of Miles' negatives actually serve to make him a more well balanced and fleshed out character. His word choice is pompous and over the top because Miles himself is pompous and over the top. He's a frustrated writer living in Los Angeles who's also an oenophile...if Miles was depicted as anything less than an up his own ass snob (in spots) then I'd have to ask Mr. Pickett if he'd ever even HEARD of Los Angeles, let alone been there.

Jack, Miles' equal but opposite is a great foil and serves as one of the best character counterpoints I've seen in recent literature. How is this not better evidenced than in both of the characters chosen professions? Miles the writer and Jack the actor. The former a cynical and inwardly focused (read: OBSESSED) lover of fine culture (wine, literature, good looking women who like those things) and the latter a boisterous, charming, slightly air-headed but almost inevitably likable actor who likes good food. good times, and good looking women. Their love of 'the grape' and the fairer sex seems to be what unites them, and nearly splits them, at least at first. But what separates this novel from most 'buddy' stories' is the real depth given to the relationship between the two male leads. Miles and Jack need one another to such an extent they seem to be a variation of Plato's hermaphroditic ideal, in this case the halves constituting the best possible man. But best possible being sometimes as elusive as that damned old abstract 'perfection', their eventual separation has to happen. And the inevitably of the end of this stage of their friendship, that once Jack marries and must leave behind most vestiges of his single life, including Miles, is what really brings the story home in the closing chapters and gives it a resonance far more impacting than a typical 'happy' ending.

The female characters of the story, Maya and Terra (in the movie Stephanie) are excellently written as well, the former more so. Maya, to me, is the downbeat and beautiful woman, more than a little tired and bruised from the vicissitudes of life's unfortunate but all too often occurring shames, but still beautiful, still brilliant, and possibly too much of these things for most men to handle. Terra is a female Jack, though with not quite as morally flexible an outlook. She, especially later, kicks all kinds of ass (speaking of which the downward spiral of Jack's increasingly painful and bizarre hospital stays is hilarious).

What else is there to say? This book surprised me, floored me even. It showed the emotional trials and tribulations of a very realistically depicted human relationship in such a disarmingly cynical yet still funny way that I have nothing else to say except: read it, now.

And, because I'd feel remiss otherwise, the movie. I saw the movie, loved it, and feel that the book and the movie are near perfect counterparts to one another. See the movie first, experience the beauty of the scenery, the stellar acting and Rolfe Kent's wonderful original score before diving into this surprising gem of a work.
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Maybe I should invent a shelf for books where I almost cried, or books where I couldn't breathe for a few seconds while reading it. This was not what I expected, and far better for it.

Edit: probably won't be watching the film though. Don't think I could take Lyle van de Groot seriously as Jack.
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 and pinning all his hopes on his latest novel - he should know by the end of the week if has been successful in finding a publisher. But their monetary worth is not the only difference between them; big, dashing, affable Jack easily charms all he show more meets, a contrast to Miles' rather moribund nature, still not over his divorce not to mention his lack of self-worth over the lack of success with his books. Putting aside the wine and spending time with Miles Jack's main objective during this week is to get himself laid - as often as possible, not a course of action Miles altogether approves of. It all seems like a recipe for disaster, and perhaps it is - but not necessarily in the obvious way, but certainly with most entertaining results.

Jack and Miles' attraction as main protagonists is found not so much in their individual qualities so much as in their friendship, a friendship so secure that it can withstand any obstacle that befalls them, whether self-inflicted or dropped on them by others. A friendship that allows them to speak frankly and at times bluntly, that allows them to disagree and argue and even physically fight yet still come out of it all laughing. For that is the real attraction of this account, recounted by Miles, of their celebration of Jack's last week before matrimony.

I thought I might be find the oenophile aspect of the novel off-putting or at best arcane, but this is handled well, in fact to advantage in developing both characters and plot.

That this is a beautifully and (refreshingly) correctly written novel only adds to the appeal, Rex Picket is a master with words (and not just wines) and uses them to advantage.
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An author goes on a book tour of scenic New Zealand with his best friend and his special needs cat. Sounds wonderful, right? Not so much. Billed as hilarious, the first 3/4 of the book is almost exclusively potty and sex-based (bordering on assault) humor. I enjoy a good potty joke, but these were just gross. When the best friend goes away, leaving the author with his precious cat (who saved the book from a pan), the book improves. Not recommended unless you want to read about a sweet relationship between a special needs cat and a man. Do have your dictionary handy! I had to look up the $25 (as opposed to nickel) words at least every other page and often multiple times on a page. What does flagitiousness mean anyway?
½
I loved this book. Despite it being about two very blokey blokes obsessed with drinking, fighting, golf, screwing and more drinking it was a riproaring ride with some laugh out loud moments, beautifully crafted prose and lots of quite poignant moments too. I used to know someone a little like Miles and recognised the self-deprecating, self-loathing yet charmingly engaging character. Luckily, I don't think I've known any Jacks in my life! Defininitely worth a read if you want a page turner with the power to transport you to sunny California while reading about two bosom pals.
½
Miles and Jack are two wine lovers with a wild weekend in California wine country ahead of them. Jack is about to get married and Miles is taking him on an educational tour of some great pinot noir wineries. But Jack has his own private plan to get as much pussy as possible before he is forced to settle down. Meanwhile Miles, a struggling writer, is dodging creditors and waiting to hear back about a book his agent is shopping around.

This book reads like fictionalization of a bad romantic comedy. The action is fanciful and the writing itself is overwrought. The author sounds like an over-zealous but well-read 8th grader who is desperate to show off his vocabulary. At one point, while describing a sexual encounter, the author actually show more uses the phrase, "I went spelunking for her clitoris." Gross - and extremely anatomically incorrect. Does the author really think that the clitoris is located deep within the vagina? Or is he just really excited to use a multi-syllabic word? Either way, the image it summons up is the opposite of seductive. Alas, this was not an isolated incident.

Beyond the perpetually distracting prose, I just don't think I'm this book's target audience. I like wine, but this book wasn't really about wine. The characters weren't particularly interesting and the plot was super far fetched. This is probably one of those rare incidences where the movie is better than the book.
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So much better than the movie! And I liked the movie!

I was surprised (I know I shouldn't've been) that there was SO MUCH MORE to the book than the film. And I'm a screenwriter. And prolific reader. Why was I surprised?!

Now I'll have to watch the movie again and compare what I (or they) missed - and why.

The book was a little sluggish to get started (I remember how that was cleverly adapted to the film, actually! ;-) ) but the book was SO MUCH FUNNIER and DEEPER - than the flick (at least to my recall, I'll edit this if I'm misremembering the viewing - it was a long time ago!). But the wine talk kept you entertained as the plot slowly unfurled - and ramped up.

Really, what a lovely book! A fun, entertaining read.

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Common Knowledge

Canonical title
Sideways
Original publication date
2004
People/Characters
Miles; Jack
Important places
Hitching Post; Windmill Inn
Related movies
Sideways (2004 | IMDb)
Dedication
To Roy and Julian, partners in wine
First words
The sun poured bright parallelograms of mote-swirling light through the venetian blinds of my rundown, rent-controlled house in Santa Monica.
Last words
(Click to show. Warning: May contain spoilers.)I accepted her waiting arm.

Classifications

Genres
Fiction and Literature, General Fiction
DDC/MDS
813.6Literature & rhetoricAmerican literature in EnglishAmerican fiction in English2000-
LCC
PS3566 .I316 .S55Language and LiteratureAmerican literatureAmerican literatureIndividual authors1961-
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Statistics

Members
793
Popularity
35,254
Reviews
27
Rating
(3.84)
Languages
5 — Czech, English, French, German, Italian
Media
Paper, Audiobook, Ebook
ISBNs
24
ASINs
5