Rex Pickett is tall, funny, brutally honest and unfailingly energetic—even when exhausted and hungry. In conversation, he is passionate and personal, spontaneous and astonishingly self-critical. He speaks in a stream of short to medium-length proclamations, suggestions and confessions, strung all together like one long sentence that, on occasion, will go on for several uninterrupted minutes.

Pickett is not humble, exactly. He is on record as saying that Pinot Noir might not be so popular today were it not for him, but he has a habit of being more or less right about such statements. He really is responsible for the popularity of Pinot, though he would add that Pinot itself has something to do with that. For the record, he’s also responsible for a decline in popularity of Merlot, though he adds that Merlot might itself have something to do with that, too.

Pickett is, of course, the author of the novel Sideways, the inspiration for the Oscar-winning 2004 film by Alexander Payne that stars Paul Giamatti and Thomas Haden Church. The film, a road-movie through the wine country of Santa Ynez north of Santa Barbara, follows Miles, a sad-sack writer with a passion for Pinot Noir, and his best-friend, Jack, an aging Hollywood actor with a touch of sex addiction and a hankering to sow some final wild oats before getting married. The film famously allowed Miles to insult Merlot drinkers so hilariously that vast hordes of people stopped drinking the stuff.

After following up Sideways with two sequels, Pickett has spent the last several years adapting the original novel into a stage play. After test runs of earlier drafts in Santa Monica, San Diego and London, the completed version is about to receive its world premiere in Santa Rosa, courtesy of Left Edge Theatre and director Argo Thompson, with a mighty assist from actor Ron Severdia, who not only plays Miles in the show, but also had a hand in convincing Left Edge to take a crack at reinventing the play.

Last month, at the start of rehearsals, Pickett visited the cast and crew for several days, making final suggestions and alterations. During that time, he sat down with me for a nearly two-hour conversation.

Here are some of the juiciest moments.

THE BOHEMIAN: The Left Edge Theatre production of ‘Sideways’ is being billed as a world premiere, but there have been one or two previous stagings of the play, or some version of the play. I assume this is the latest incarnation of a show that has basically been in various stages of early development until now?

REX PICKETT: OK, here’s the story. It’s kind of crazy, because theater is kind of crazy. First of all, yes. This is the world premiere. An earlier version of Sideways was done at the Ruskin Group Theater in Santa Monica in 2012, in a tiny 50-seat theater, and then another incarnation was done at the La Jolla Playhouse in 2013—
a much bigger production.

And how’d those productions go?

They went great, but I learned a lot. Look, I’ve written novels, but this is my first play, right? And early on, it was a very difficult play. Really funny, but hard to stage. My script had 23 different scenes, with complete set changes between every one. The director of the San Diego version, Des McAnuff, who directed Jersey Boys, said that Sideways was the most difficult nonmusical he’d directed in 38 years.

You sound kind proud of that.

Well, yes and no. I was trying to make the play feel like the movie, because I know how much people love the movie. It’s a road movie, so I wanted the play to have that same sense of forward momentum and drive. A lot of quick scenes, one after the other, does have a sense of propulsion.

Anyway, after La Jolla, I was sort of waiting for the show to maybe go to Broadway. So I’m sitting there waiting and waiting. And Broadway didn’t happen. So I took the play to London last summer, and we had a run of it there at the St. James Theatre.

This was still the 23-scene version?

Yes. Reviews were good but mixed, and the scene changes were part of the problem. At La Jolla Playhouse, they used rear-screen projection, hot tubs coming up out of the floor, cars driving across the stage. That’s how the scene changes were handled. In London there was a kind of a turntable on the stage, but it’s an old theater, and it didn’t always work.

That was a little over a year ago. How did you end up deciding to bring the play to Northern California, and to Left Edge Theatre, another ‘small black box’–type place?

Well, Ron Severdia, who works with Left Edge Theatre, had been tracking the play for several years, writing me all these emails asking when the script of Sideways would be available. And I kept writing Ron back, saying, “It’s tied up. It’s still tied up.” But he kept at it, and I have to say, his determination and the ideas that came with the proposal, were very appealing.

All this time, I have been focused on getting the play into bigger and bigger theaters, but Ron’s thought was, this play should be in a lot of theaters all over the place, that it should be published in a version that is accessible—and not so technically challenging—for theaters large or small to produce. He told me that he and Argo Thompson, the [Left Edge Theatre] director, had an idea to take those 23 scenes and simplify the transitions, without losing a line of dialogue.

Let me be clear. I loved the La Jolla production, with all the fancy stagecraft a big, well-funded theater can do. And the London production, too. They were great. But what I learned from those versions is that the story of Sideways is really about connection, it’s about conversation and dialogue. And that’s what Ron and Argo convinced me of—that to really work, this story should be stripped-down to what makes it great. And that’s the relationship between Miles and Jack.

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So I thought, “Wow! If we could just start over and rethink this thing, and make it truer to the book than to the movie, then maybe we’ll have something that can be done in theaters all over the world.” This play still takes you through a week in these guys’ lives, but it does it in a way that we’ve not tried before. So, yes, this is a changed version, a new version, and this is the one that Samuel French will be publishing and making available to regional theaters in the U.S. and beyond.

And to be honest, I now believe that this is the version that could end up on Broadway. It’s that good. Though Broadway is pretty congested these days. It’s mostly just shows with famous stars eager to show they can really act, or big splashy musicals.

Have you ever considered adapting ‘Sideways’ into a musical?

[Long pause] Honestly? Uh, yes. In fact, I’ve already done it. I’ve written the libretto for a musical version of Sideways, including writing the lyrics for all of the songs. And, yes, there’s a song about not liking Merlot. I’m working with a brilliant composer, who’s doing the music. I have no idea if it will ever be staged, but it was something I just had to do.

I imagine Miles would say some fairly acerbic and hilarious things if Jack told him they were making a musical out of one of the worst weekends of his life.

I might have said those same things once. Actually, I have said those same things. I don’t like musicals, with very few exceptions. And if this ever does happen, I think Sideways:
The Musical will be one of those exceptions. Like the nonmusical version, it defies expectations.

By the way, I am Miles—you realize that, right? He’s based on me. There’s a lot of truth in the novel. He’s me. More or less. In the movie, Miles is kind of a wine snob, but in the book, not so much, because I’m not really a wine snob. I like wine. I like going to wine tastings, and I wrote the book because I’d been going to wine tastings in Santa Monica. Those people weren’t wine snobs either. I went there because I liked wine, and because it was my only social outlet at the time. Sure, there would be doctors and lawyers sometimes who’d try to prove they knew more about wine than me, but I mostly ignored them.

And the thing is, like me at the time, Miles had no money. I made two feature films in the 1980s and then went through a divorce, and I did not have a lot of expendable money—I still don’t, to tell you the truth, though everyone assumes I’m super-wealthy—so I’d go up to Santa Ynez Valley, to a golf course called La Purisima. It’s now surrounded by Pinot Noir, because of Sideways. I’d go up there for the weekend, and I’d stay at a place called the Windmill Inn, which has now been rebranded as the Sideways Inn.

Can they do that?

Evidently. I called an intellectual-property lawyer, and he said, “Sorry, Rex, you can’t own the word ‘sideways.’ It’s now the Sideways Inn.” And I discovered the place and made it famous.

I used to be able to go up there and play golf and spend the weekend for next to nothing. And winetasting was free. Now, because of Sideways, the place is overrun with tourists all the time and I can’t afford to go there all that often anymore. How’s that for irony? I’m not saying I’m bitter or anything. I’m really not. But I do find it ironic.

The point is, Miles is not a wine snob. Wine country is just where he goes to get away from L.A. It’s a cheap getaway. That’s what it was for me when I was just learning about wine. Most of what Miles knows about wine he got from reading about it, like me.

People come up to me sometimes, especially here in Northern California, and they want to know why Miles didn’t spend his time in Sonoma County or Napa—what some people call “the real wine country”—instead of Santa Ynez. Well, for one obvious reason, Miles lives in L.A. Santa Barbara and Santa Ynez were just closer, and it was a lot more affordable. I’ll be the first to say that when it comes to wine, Sonoma County and Napa County are awesome. I think, in terms of Pinot, Northern California has Burgundy beat. But it’s also way more expensive than Santa Ynez is. Or was, anyway.

How different is the play from the movie?

The play is funnier. It’s also a little bit darker.

Here’s the thing. The movie was based on my book. The play is based on the book, but not on the movie. I love the movie. I never get tired of watching it. It’s a very faithful adaptation of the book. I thank Alexander Payne for keeping it so faithful. In another filmmaker’s hands, it could have been two guys doing Jell-O shots in Cabo. But he did make some changes. In the movie, Miles is a schoolteacher. In the novel, he’s an out-of-work screenwriter. In the movie, he’s a bit more of a snob than in the book. In the book, his whole life is filled with dysphoria. He’s divorced, he can’t get published, his friend Jack is . . . well, he’s Jack. What Miles needs in his life is some euphoria, and winetasting is that euphoria. It gives him something poetic he can feel a bit of mastery over.

So to answer your question a different way, the difference is that the movie was very faithful to the book, and the play is even more faithful to the book.

Miles is based on you, you’ve pointed out. Unlike Miles in the book, though, you’ve now had a major literary success. So say a little more about what it is that excites you, Rex Pickett, successful author, about wine.

Wine is great. I’m going to sound like Miles, but there are so many identifiable grapes and so many different countries of origin and so many different regions and appellations. It’s subjective, too. I love the subjectivity of wine. And then every year it’s a new deal! And there are wines being cellared and bottled that we won’t know anything about for many more years. Then it could all change again. Wine is a vast world, a vast ocean of mystery—talking like my characters again—and nobody can ever master wine, not really. It’s too big. It’s like literature. You can try to learn everything about it, to read everything and taste everything, but you never will. And that’s OK, because the fun is in trying. The fun is in learning.

That’s what I love about wine.