Image Credit: Amazon.com

Sideways has, and forever will be, one of a handful of go-to movies for me during times of distress. “Comfort food,” which lovingly assuages the psyche and assails any external factors meaning to do irreparable harm to my person. It (along with a few other films in my secret arsenal of cinematic panacea) has been the decisive antidote for mental and emotional disconcertment, something I’ve needed a shit-ton of in 2020. Well, can you imagine my excitement when I recently discovered that the book the film was based on is one of a trilogy of stories following the exploits of Miles and Jack? I now not only had one, but two books to satiate my unquenchable thirst for these characters Rex Pickett created!

So, without a moment’s more hesitation, I immediately bought all three on my Kindle. But, being the weird completist that I am, of course I had to begin with the first novel, even though I’ve seen the film several hundred times by now. I’m glad I did, however. There were a lot of significant differences in it that are referenced in Vertical which would have confused me had I not read Sideways beforehand. And, I mean, come on! Being a fan of the film, how could I not read the book that started it all? It would have been downright blasphemous to deny myself the pleasure!

And, yes, Sideways “the novel” was just as friggin’ fantastic as the film. We even got a more optimistic future for our boy Miles.

That is, until you read its sequel.

*sigh*

Now, before you traverse any further, if you have yet to read Vertical – stop! I don’t want to ruin the enjoyment of the sequel if you have yet to breathe it all in; but definitely come back once you have.

We good now? Great! Onwards, my good lads and lasses…

Vertical takes place seven years after our dynamic duo had their notoriously ridiculous adventures up in Wine Country. And the tables, as they say, have turned. Miles is a celebrated author – quite the hugely celebrated author, that is – whose debut novel about his real-life misadventures with Jack has been adapted into a film. This film (like Rex Pickett and his adaptation of Sideways) has catapulted Miles out of the “commoner stratosphere” and into the celebutante lifestyle, as well as irreversibly changing the Wine World forever. And because of the attention that his book and film adaption have brought to the vignerons and their beloved grape, Miles is a hot commodity. The ladies wanna ravage him and all of Hollywood is salivating for more.

Jack, on the other hand, has been having a rough time. His infidelity and drinking has finally caught up with him, and he now finds himself without a wife, a family, and a career. So, naturally, it’s time for yet another whacky adventure with his buddy Miles, right? Abso-friggin’-lutely! Only this time, Oregon has the honors of hosting their shenanigans; but that’s just the frosting over the proverbial wine cake. The crux of the story revolves around the relationship between Miles and his aging mother. His mother has been debilitated by a stroke, and can no longer care for herself. So, instead of leaving her in a nursing home, Miles decides to grant her a final wish: transporting her to her sister’s house in Wisconsin. So, with Jack, his mother, her caretaker, and his mother’s dog, Snapper, in tow, another adventure begins anew.

Truth be told, the book wasn’t exactly what I had expected going in – but that turned out to be a really great thing. Yes, there are a lot of similarities to the hijinks in Sideways – a book sans these two knuckleheads and the trouble that seemingly follows wouldn’t be a “Sideways” story after all, now would it? However, there was an emotional core to it that didn’t exist in its predecessor. And by the the end of the book, the heaviness of “life” has changed some of our characters for the better. This was a surprising, yet welcomed progression of the story and its cast.

Vertical reconciles all of the loose ends left bare for us to ponder over in Sideways. But in doing so, it replaces them with additional questions in need of answering. The silver lining, however, is that this time, we already have a finale waiting in the wings for our beady little eyes to feast on. The conclusion to Rex Pickett’s magnum opus is appropriately titled Sideways 3 Chile – a title which will make sense once you’ve finished reading Vertical.

I thoroughly enjoyed reading this. Not only is Rex Pickett one of my favorite writers, but these two stories permeate a sense of reality that I can relate to on some level. Not that I’m as nuts as Miles or Jack (at least, in my mind I’m not), but there is a little bit of both in me, especially in recalling the experiences of my 30s going into my 40s. And the emotional turmoil that Miles finds himself facing in Vertical is something that we are all going to involuntarily confront at some point in our lives, if we haven’t already.

I can’t wait to crack open the finale to this saga. I’m simultaneously excited and sad to find out how the story ends. It’ll be bittersweet, no doubt. But that’s the great thing about words, and the memorable stories birthed by their symphonious coalescence: they never leave our side.