IS THE (WINE) GLASS HALF FULL? Interview with Rex Pickett… by Marco Mannone


This article / interview is by a writer, about a writer, and for writers. Fans of the film Sideways will surely enjoy the following conversation with author Rex Pickett as an illuminating exposé on the genesis of his beloved story and its memorable characters. However, by design this piece is not intended for the casual cubicle-worker taking a quick coffee break. Our discussion evolved into an in-depth analysis of writers, the writing process and the publishing industry as a whole.

We here at Forth pride ourselves on digging deeper than the surface most other publications merely scratch. Without oppressive printing-costs to cut us off at the knees, we can indulge ourselves above and beyond the claustrophobic brevity that is generally imposed on standard Q & A’s. For those of you with a crippling case of A.D.D. your time is probably better spent watching the latest cute animal blunder on Youtube. For the rest of you: pour yourself a choice glass of wine, kick your feet up, and enjoy this one-of-a-kind conversation about failure, perseverance and how a writer boldly chose to follow-up his enormously popular novel-turned-Academy-Award-winning-movie.

Continuing the Dionysian exploits of Miles & Jack, Vertical Pickett’s long-anticipated sequel to his now iconic Sideways — had me alternately laughing and crying through this hilarious, heartbreaking and ultimately moving meditation on Fame, Friendship and Family. I found it equally poignant and profound the way this epic road novel slowly but surely strips Miles down to his naked, sober soul — a bittersweet, existential deconstruction of everything this man is. Vertical managed to break my heart and then put it back together again, piece by piece, and should abolish any lingering doubts whether the author just got “lucky” with Sideways. This is a work to be both admired and savored like the great Willamette Valley Pinots Miles exults over (**Quoted on the back of Vertical’s hard-cover edition**). A story such as this, about real human beings experiencing real emotions, is unfortunately considered High Concept at a time when most “literary” adults are reading about vampires and wizards. Bravely dipping a pen in the ink of his own soul, Pickett’s novels chart a winding path from divorced, struggling writer in the throes of a mid-life crises, to celebrated author coming to grips with his success. A journey that should serve as inspiration for any underdog artists who feel that time — and hope — is running out for them.

I recently sat down with Rex at a coffee shop in Santa Monica to discuss Vertical and all the wine, sweat & tears that lead up to it. At 6’ 1” and with a full head of hair, the San Diego native is the complete antithesis to the nerdy portrayal of his alter-ego in the film.

MM: I admire what you’ve been through, Rex. You’ve fought the good fight.

RP: I’m blogging about it now (, but you know, even after Sideways life wasn’t rosy. Success isn’t like one of those pianos that play themselves. No. There’s a blank page. People think they’re going to write that one thing and it’s going to be the be-all, end-all, well… think again.

MM: So for those who are unfamiliar with your background, describe the catalyst behind the writing of Sideways.

RP: My life was pretty much in the shit-can. My agent had died of AIDS; my mother had a massive stroke that rendered her left-side totally paralyzed; my younger brother took over her care out of ostensible altruism and then proceeded to gut all of her savings in a mere two years. I went through an amicable, albeit disorienting, divorce with my wife – who won an Oscar for a short-film I wrote in 2000 [My Mother Dreams the Satan’s Disciples in New York.] So I was pretty much nowhere when I wrote a novel called La Purisma – named after a golf course up in Santa Ynez – and it was a mystery novel. First novel I had written since some epigone avant-garde experiments in the ‘70s. It got me a publishing agent who took it on, but we couldn’t sell it. So that’s the other thing: if you have an agent and he likes your work, you can still have trouble getting published; it’s no guarantee just because you have representation. And in the novel world, things move slowly, unlike with screenplays. The rejection letters trickle in like a slow morphine drip.

MM: The frustration of Miles Raymond comes into focus.

RP: So thus we have Miles, the guy who can’t publish his novel. I started spending a lot of time up in Santa Ynez Valley. Initially I went up just for the golf – uncrowded and beautiful — then I started staying overnight at, where else? The Windmill Inn, just like Jack and Miles. Then I had to have a place to eat, so I ambled over to the nearby Hitching Post, now an iconic landmark because of Sideways. I would always go up mid-week when there was no one on the golf course, and practically no one dining at the Hitching Post. After a few glasses of their Pinot I’d strike up a conversation and suddenly I realized: “Oh my God, there’re wineries around here!” So, frustrated with my novel La Purisima, I took frequent sojourns up there. Then, because it was so beautiful and uncrowded I started taking friends. Once I went up with a buddy of mine, Roy, and we went from tasting room to tasting room, cracking each other up. He’s the inspiration behind Jack and he said, “Rex, you gotta write this as a screenplay”, and I thought, “Yeah!” So I wrote Sideways as a screenplay but it didn’t work. It so didn’t work, I didn’t give it to my agent.

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  1. November 12, 2010 @ 2:36 pm JB

    Great interview, Marco. I (also) wrongfully assumed that Rex made a killing from the book, Sideways. And, congrats on the nice parting gift! Clearly, he recognized in you a driven writer and wanted to encourage you…keep up the good work.

  2. November 12, 2010 @ 3:14 pm alx

    Wonderfully insightful & inspirational! A must read for any aspiring creative person. Thanks Marco.

  3. November 13, 2010 @ 6:47 pm NGC

    That was a wonderfully in depth piece. It was great to hear about his trials and tribulations but also his success and advise for aspiring writers. Very refreshing.

  4. November 22, 2010 @ 5:28 pm Grotenstein

    Good stuff, Marco. You have a knack.

  5. November 24, 2010 @ 2:12 pm Graham Strong


    Just started writing my novel a couple of months ago (and blogging about it), and decided to research about publishing, etc. before I went too far down the road. I’d always known it was tough, but as Rex Pickett says, it seems to be getting tougher all the time.

    Is self-publishing the future? There are some serious cons to it, but really, if you are doing all the work and promotion yourself anyway, it makes sense to keep all the profits.

    Anyway, loved the insights into both the writing and publishing process. Great interview!


  6. December 2, 2010 @ 9:41 am Jenn

    Nice one Marco!

    great questions and great interview and an obviously endeared response to you, its obvious that only the good writers/interviewers get the special treatment! look forward to the next,

    and hey if word can spread all the way to financially challenged Ireland about how good you are things can only be on the up!! 😀

    Jenn xx

  7. November 1, 2012 @ 7:57 pm Michael C. Cordell

    Excellent interview, Marco! I realize it’s been a couple of years since you wrote it, but I recently became a Rex Pickett fan, beginning with with an in-depth blog series he wrote for Stage 32 which chronicled his experiences with Sideways and life thereafter. I read Sideways (and finally saw the movie!) and just finished Vertical, too. This weekend, I’ll be seeing Sideways, the Play, that Rex wrote based on the book (not an stage rendering of the movie).

    I’ve been following Rex on Twitter for several months now. He seems to be one of the least effected literary people I’ve ever met, an iconoclast of the first order, as sincere as he is talented. You were able to illustrate those very attributes in your interview.

    Congratulations! I hope your writing has blossomed since this was first published.


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