Vertical, the sequel to the wine novel Sideways that was made into an immensely popular movie in 2004, is really two books in one. Rex Pickett’s follow-up to what the cover bills as “the world’s most beloved wine novel” is, for about three-quarters of its length, almost un-put-downable — hilariously funny, boozy, raunchy, and filled with guilty pleasures that will make you laugh out loud, cringe and groan at appropriate moments. That’s the first book. The second, which breaks upon the reader abruptly and without warning, is dark, depressing, tragic and filled with deliberate emotional anguish and awkwardness, though its heart is undoubtedly in the right place. I’m not sure yet whether bolting these two stories together is a stroke of creative genius or a serious flaw that diminishes the overall novel tremendously. On the whole Vertical is pretty enjoyable, but it has some significant issues.

Disclosure: Loose Gravel Press, the publisher, gave me a free copy of Vertical in exchange for an honest review. This review does contain some spoilers.

The story won’t make any sense to you if you don’t know Sideways, but don’t worry–having seen the movie is enough to get you up to speed. Some years after the events of Sideways, Miles Raymond, a novelist and oenophile, has struck it big with his novel about wine, Shameless, which was made into a hit movie. (Yes, it’s metafictional). Now rich, booked with publicity and writing offers and full to the gills with free samples of Pinot Noir, his favorite wine, that winemakers have been giving him for free, Miles has broken up with his Sideways girlfriend Maya, who’s become a vintner herself, and is using his fame to have affairs with various wine-loving women. Clearly he thinks his long years of sipping rotgut $5 Merlot are over.

The infamous spit-bucket scene from Sideways! This gag is referenced, very metafictionally, in the opening pages of Vertical.

The story really gets going when Miles, who lives in the L.A. area, is invited to MC a Pinot Noir wine festival in Oregon. Deathly afraid of flying, Miles decides to drive up to Oregon and to bring his friend Jack, a now out-of-work actor who’s down on his luck and who caused much mischief in Sideways. But in addition to this errand Miles seizes the opportunity to break his handicapped mother, Phyllis, out of her prison-like assisted living facility, deciding he’ll drive her to Wisconsin, her old home, to live out her final years with her sister. Phyllis has had a stroke, is in a wheelchair and is inseparable from her pot-smoking Filipina nurse Joy and her yappy dog Snapper. Miles rents a handicapped van, packs the back with wine and the motley crew start the boozy trip up to the Willamette Valley, meeting a series of minor comic disasters along the way.

Constructed this way, Vertical is a classic “road trip” story, which entirely makes sense because Sideways was too. Pickett flings one after another comic and tragi-comic set-pieces at us, and they’re pretty funny and cringey at the same time, which is exactly how they’re intended. Recreating the most famous scene from Sideways, Miles, at a wine event, empties a spit bucket over his head; the moment is captured by a cell phone camera and goes viral on YouTube. He and Jack meet two foxy girls from Spain and proceed to pair off, but Jack overdoses on Viagra and winds up in the hospital with priapism, resulting in a gory but hilarious emergency room scene. Miles’s mother gets an impacted molar that they don’t have time to remedy if they’re going to make the Pinot festival, so Miles convinces Snapper’s veterinarian to pull the tooth with dental tools designed for animals. The wines that Pickett describe blast forth in bacchanal glory. He gives a list of them at the end: Bonaccorsi Pinot Noir 2007, St. Innocent Freedom Hill Pinot Blanc 2008, etc. It’s all great fun, and in fact even more radical and daring than Sideways, whose antics seem tame by comparison. Pickett’s a genius at comic, satirical writing, and he’s mostly poking fun at himself.

Author Rex Pickett talks about Vertical–and why he doesn’t drink wine anymore.

Unfortunately the fun ends quite suddenly. Phyllis’s health takes a turn for the worse at the Pinot Noir festival, Snapper gets his leg nearly ripped off by a car, Joy deserts the group after being accused of stealing and Jack goes home, leaving Miles to transport his invalid mother thousands of miles across the country to Wisconsin alone. This part of the book is about Miles finding himself and bonding with his mother, but the last quarter of Vertical is one of the most depressing stories I’ve read in a long time. There’s no more wine, no more laughs and no more fun. The story is deeply and intensely personal and Pickett, who dedicated the book to his mother (who died in 2000), is obviously laying his heart bare to us. As I said that heart is clearly in the right place, but I really had a hard time getting past the sudden and abrupt change of tone and the descent into darkness. Finishing the book was a real slog for me, something I totally didn’t expect as I flew eagerly through its first three quarters.

I think both stories in Vertical, the fun boozy wine story and the heartfelt family story, are certainly valid, and Pickett obviously had a lot to discover about himself in each of them. What I can’t figure out is whether the decision to bolt these two stories together was itself a bad one, or whether the job of integrating them wasn’t done right, but something obviously didn’t work for me. It’s a bit of a tall order to transition between gags involving spit buckets and Viagra mishaps to a very serious story about dying, broken families and alcoholism. As I was turning the final pages I found myself wanting to put the book down and go have a glass of wine.


This is not technically one of the wines featured in Vertical, but it’s from the same winery–Elk Cove Vineyards of Gaston, Oregon–as a Pinot Gris that the characters drink on page 235.

Still, that said, Vertical is a lot of fun, and on the whole I think wine lovers will enjoy it. The book has a few technical peccadilloes–some editing and formatting errors, for example–but they don’t detract too much from the experience, and the evocative line drawings by Michele Phillips are quite charming. For its first three quarters, Vertical is probably better than Sideways, more outrageous and more fun. The last quarter is dense, depressing and not very much fun at all. As I said, it’s really two books. How well they fit together with each other I think will lie mostly in the eye of the beholder.

Grade: B

Note: Vertical was evidently originally published in 2011. I read the 2016 reprint, which I understand has some changes from the first printing. I have no idea what those changes might have been or how extensive.

The cover of Vertical is copyright (C) 2016 by Loose Gravel Press. The two photos are by me and are copyright (C) 2016 by Sean Munger, all rights reserved (no claim, obviously, to the Vertical cover design). I am not the uploader of any of the YouTube clips embedded here.