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Interview With Author Rex Pickett: Up, Down, and Sideways

By Vera Caccioppoli

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Rex Pickett’s house is on a quiet tree-line street in Santa Monica. As I approach the porch to the quaint bungalow, I see that the front door is wide open. At the open door, I can’t find a bell, and there’s no one visible inside. “Hello?” I call. No response.

I’m here to interview Pickett, who wrote the novel Sideways. The writer who helped change the landscape of the Central Coastal Wineries, the writer who created Miles and Jack, two middle-aged college buddies out for one last hurrah before Jack’s wedding. Miles, the despairing unpublished novelist and Jack, the optimistic one-time bit soap actor, on a road trip, not to recapture something, because the point is their dreams have eluded them. More of the road is behind, than ahead, of them, and they feel the pinch, the narrowing of life’s possibilities.

I take this odd moment on the threshold to capture Rex Pickett’s wide-open abode in repose. A bike leans against a wall, mail is strewn on a table, non-descript bookcases are loaded to sagging point, two framed movie posters, From Hollywood to Deadwood and Sideways, provide the only art. The furniture is utilitarian, the room well lived-in. It is devoid of pretense. No hint of affectation.

I call out again, louder, and he appears, striding across the room to greet me. He’s tall with movie-star good looks. His greeting is both warm and cautious. And when we settle in, he says “What would you like to know?” He’s intense, engaged, willing to answer, to share.


Rex Pickett is a puzzle. He’s a produced screenwriter whose very first novel is made into a hit movie. But Pickett, the screenwriter, did not write the screenplay.

Pickett’s circuitous career leading up to Sideways accomplishes what all stories need to achieve: it reveals character and unleashes conflict and opposition in the character’s path. It is, in effect, a classic Hero’s Journey.

A San Diego native, Pickett was raised in Claremont and attended UCSD. Like most “overnight success stories,” his was decades in the making.

He started writing poetry, lots of it, as a teenager. But at 19, he threw all of it in the trash—all 1000+ pages. To understand why, is to understand a basic truth about Pickett: He has high standards, and he abhor's banality.

“It wasn’t good enough. I wanted to start over,” he says, “with a clean slate.”

Pickett isn’t a man who takes the easy path. While at UCSD, Pickett took two semesters off to do some reading “It was a period of autodictaism and aesthetics.” Turns out “some reading” included Carl Jung’s collected works, a 20-volume set. “It will teach you all you need to know about characterization,” he says. “Well, at least Volume Six,” he adds with a grin.

More advice: Avoid all screenwriting books devoted to structure, plot paradigms, theories of outlining and plotting. “If you are a storyteller,” he says with certainty, “the three acts will happen unwittingly. It’s this simple: Beginning, Middle and End. And let me tell you this, if a storyteller doesn’t know this intrinsically, he’s not a writer.” Then he tips back in his chair and indulges a smile, “Trying to understand screenwriting that way—it’s like having sex in a wet suit.”

He wrote five screenplays before From Hollywood to Deadwood, his first theatrical release, was made. He’d written and directed a couple of small films. And in 1999, a script he wrote, My Mother Dreams the Satan’s Disciples in New York, won an Academy Award for best live-action short. It was directed by his then wife, Barbara Schock. The script reads like literature, perfectly rendered. “It was written,” Pickett says, “without compromise and directed without compromise, it moved from the page to the screen as purely as one could hope for.”

But then, a rough patch. He wrote a detective novel that garnered interest but no publishers. His marriage ended. His mother had a stroke. Financially, creditors were held at bay as Pickett made desperate phone calls to family and friends. “I had to take in a roommate, to make the rent,” he says, pointing to one of the two bedrooms. “I moved into my writing room. I considered myself a failure. It was the lowest point of my life.”

The Beginning

From that desperation, Sideways was born.

“Sideways is a very personal work, confessional,” Pickett says. The intensity with which this is stated leaves little doubt “I bared my soul. I am Miles.”

He says this without addendum, without qualification. He lets his words stand naked despite the implications of this statement, the silent tabulations that the listener naturally makes. Like the décor of his home, what you see is what you get. Picket doesn’t attempt to add pretty corners or waxed floors. He lets the truth do what it will.

The humanity of Sideways, the novel and the movie, is in its ability to move between comedy and tragedy, from moment to moment. At its best, it is both at the same moment. Pickett knows something about this.

“I knew if I was going to write about failure and despair, I better lace it with humor," he says. "My first film was despair without humor and it ended up selling to German television. They were the only ones who were into just despair."

He originally started Sideways as a screenplay, “but it didn’t work,” he says. “It was all events and no interior voice. Then I began a short story which evolved into the novel. I realized that in writing it as prose and in the first person that I was able to use the interior monologue of Miles to give a perspective on the trip that the screenplay didn’t have.”

After writing the book, Pickett tried to adapt it into a screenplay. “But it was like many novelists adapting their own work: my version read like a series of scenes from the book. The best adaptation comes from good screenwriters who aren’t afraid of changing things, screenwriters who have their own vision of what the book should be—as a film.”

Like his story’s character Miles, who spends his trip with Jack waiting to hear from his agent about his latest manuscript, Pickett’s future was riding on his own unpublished novel. His agents shopped Sideways simultaneously to the print and Hollywood folks. Nine months later, when it seemed that his last chance had run out, Sideways was pulled out of the reading stack by a young assistant to writer/director Alexander Payne (Election, About Schmidt). Pickett praises Payne and his writing partner Jim Taylor on their script. Sideways went on to be nominated for 5 Academy Awards, including Best Picture. And, with irony abounding, its only Oscar went for “Best Adapted Screenplay.”


“It’s all about characterization,” Pickett says intensely, leaning forward. “Without characters, you have no story. Characters are alive, breathing, and if you’re honest about your work, you can’t make them do something against their nature.”

Pickett develops the characters in his head first, then the story. “My characters are living beings in my mind.” He uses characterization and dialogue to create differentiation. “Opposites attract and create conflict; create tension. Miles and Jack are opposites.”

Miles is introverted, and for him the glass of wine is always half empty; and Jack is the extrovert, his glass is always half full. “Miles loves Jack’s ability to walk into a restaurant and light up the room!” Pickett says, his eyes alive, as if he just started to talk about a lover. “You gotta love Jack, the way he can turn any situation around and make it seem positive!”

In the screen adaptation, Payne chose to give Miles a respectable job, teaching eighth grade. In Pickett’s novel, Mile’s has nothing solid to fall back on, nothing to make failure palatable. Only the free-fall of despair. It makes failure cost more and is one of the biggest differences between the novel and the screenplay.

It’s also the way Pickett has lived his life.

“I’ve known some talented people who didn’t have the courage to follow the path, and I’ve known some mediocre ones who were so obstinate about making it that they just bulled their way to success. The need writers have to express themselves grips them, some more intensely than others. And you either have the courage to follow that path or you don’t. That’s not fate, that’s choice.”

He believes in free will, hard work, and having the goods when luck shows up. As for God? “It is for me the Unknowable thing—call it, like Jung, the Unconscious—that entity greater than me who descends on me with dreams, ideas, fears, exhortations. I do feel there are forces outside my ability that are shaping me, annealing me in some invisible way. But I don’t surrender to organized religion, to a being greater than me who’s puppeteering my fate and decreeing whether, at the Rapture, or my death, whether I’m headed to heaven or hell. If Heaven is where shallow-thinking people are going, then I’ll take hell. And at least I know I’ll be in good company with other artists. Plus the wine will be better.”

Endings, though, are important. “I saw an early draft of Payne’s screenplay in which the movie ends with Maya’s long phone message to Miles. “If it ends like that,” Pickett shakes his head, puts his right hand to his temple and mimes pulling the trigger of a gun. “Might as well hear a gunshot.”

The movie doesn’t end like that, though. The last scene is of Miles on Maya’s doorstep, ready to try again, knocking and waiting. “There has to be a sense of hope and redemption,” Pickett says.

“I believe in the innate need to write—in whatever form—and then whatever happens, happens,” Picket says. He never expected the writing life to be easy; he expected sacrifice. “I have never thought that art should pay bills. I think writing as a career comes second to writing as life.”

But don’t mistake him for a saint. Pickett says that he has thought of selling out, writing for commercial success, “Look, in desperate moments I think: What would make me a lot of money? But it’s hard to fake. It’s hard to be good when you’re faking it.”

In Pickett’s absolute world, there’s this strong sense that if you lose your integrity, you lose you soul.

“That’s a price too high to pay,” Pickett says in his intense way. “What you’re doing is what you’re becoming; what you’ve done is what you’ve become.”


Pickett’s living room turns into a cluster of shadows as the sun recedes. Perhaps being semi-cloaked in darkness, Pickett’s humanity, his vulnerability, lies closer to the surface. He seems spent by his own intensity.

He is Miles—but with a different ending. And so now is the time to ask the question I have been turning over in my mind through the afternoon: Are you happier now, since Sideways?

Pickett exhales and leans back in his chair. “I’m certainly more comfortable than I was before.” He explains, “I still possess that same sense of pressure to write better, to dredge out of me the deepest, most truthful expression of my—if I can be so arrogant—artistic being. And Sideways seriously raised the bar on what I expect from myself.”

And from what others expect as well. But the question hasn’t been answered. So I again ask: Are you happier now, since Sideways?

Pickett’s fingers make a tee-pee and he leans his chin into them. As I wait for him to speak, I think back over the interview, about how for the first time in his life he’s being paid an advance (Knopf) for his next novel, how he’s bombarded with requests for appearances at wineries and readings and book signings. And I think about Miles, Pickett’s autobiographical character. What if Miles’s agent had called to give the happy news that his novel had been sold? How would that have changed the story? What would Miles’s reaction have been? Initial euphoria, yes, and a splurge on a pricey Pinot—but beyond that, what? Would success have helped Miles get over his obsession about his ex-wife? Would he drink less? Would he chose the “light” over the “dark”?

Pickett finally speaks, through his interlaced fingers. “Happiness is, for most people, contentment. But contentment for an artist is death.”

In preparing for the interview I had read Pickett’s explanation on how success had changed him: "I drive a car now that, when you get in it, it smells like it's going to start." I liked the wry understatement.

But I ask again, for a third time: Are you happier since Sideways?

There is a long beat.

Then Pickett answers.

“No. I’m not happier.”

© 2007 Vera Caccioppoli

About Vera Caccioppoli

Vera Caccioppoli, MFA, is a screenwriter. She is the founder of Hi-Way-Haven, A Place for Writers in Encinitas, California, where she teaches screenwriting, leads screenplay workshops, and provides script analysis for a national clientele. Vera's articles on screenwriting are available free of charge on
Screenwriting Article by Vera Caccioppoli

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