Author Interview: Rex Pickett (“Sideways”)

by John Robert Marlow

Rex Pickett, author of Sideways and Vertical

Rex Pickett is author of the novel Sideways. The modestly-budgeted film adaptation (written by Alexander Payne and Jim Taylor) earned over $100M at the box office, and was nominated for five Academy Awards, including Best Adapted Screenplay (which it won) and Best Picture.

Rex has also directed, and has written several screenplays himself, including My Mother Dreams the Satan’s Disciples in New York—a film that won an Academy Award for Best Live Action Short. His most recent novel is a Sideways sequel called Vertical.

Rex blogs at

JRM: How did the Sideways adaptation come about?

RP: We went out to both film and publishing simultaneously. The publishing industry loathed the book in no uncertain terms, and we pulled it after 16 rejections because my book agent didn’t want to stink up the rest of the publishers in the event we did a film deal.

But the film world turned it down universally as well. You hear about rejections in publishing, because your agent gets rejection letters and sends them on to you. In film, you generally don’t hear anything. And I didn’t.

“The publishing industry loathed the book in no uncertain terms. The film world turned it down universally as well.”

Miles gets the news from his agent (Sideways)

My agent was at Endeavor [now William Morris Endeavor], which also represented director Alexander Payne. My agent passed the unpublished manuscript to Alexander’s agent. It took nearly a year before Alexander read it. During that year, no publisher and no film company wanted it. So when he called, it was literally out of the blue. A miracle, really.

He optioned the novel, and he and his writing partner Jim Taylor adapted it for the screen without a production deal, knowing that after About Schmidt and Election [also adapted by Payne/Taylor] they would probably have no trouble getting one.

A lot of credit goes to Alexander’s assistant, Brian Beery, an unsung hero in the whole success of Sideways, because he was the first one to read it and pass it along to Alexander with a ringing endorsement. Otherwise, it’s unlikely he ever would have read it.


JRM: Can you say what the option was like—was it one of those legendary $1 options, or something that actually put wine in your glass?

RP: It was $12,500 for one year, first right of refusal [right to extend the option] to Alexander Payne after one year, my right to refuse after the second year.


JRM: The book was still unpublished at this point.

RP: Yes. The Japanese foreign rights were bought, and I thought for a while there that I was going to be the only first-time novelist who couldn’t read his own published work. But the Japanese sat on the rights and waited until there was a movie before going forward with publication.

The American book was sold before there was a film deal, and was published about 6 months before the film was released. Looking back, I wish I hadn’t taken the measly $5,000 advance from the publisher. Had I waited until the film was released, I’m told the book would have sold for $1,000,000.00.

“Looking back, I wish I hadn’t taken the measly $5,000 advance from the publisher. Had I waited until the film was released, I’m told the book would have sold for $1,000,000.00.”

JRM: So you didn’t know it, but you were in a position—because you had both a book and a screenplay—to use the success of one to up the selling price of the other by 20,000 percent.

RP: RP: The success of the movie would have steeply driven up the price of the book. Holding out until the release of the film would have been tantamount to placing a bet where I had little to lose and everything to gain. Agents are always eager to do a deal, when sometimes patience—and more prudent advice—is what’s needed.


JRM: What was your level of involvement in the adaptation itself—the process of turning the book into a screenplay?

RP: Very little. They were generous to give me every draft of the script. I was so thrilled with how faithful it was to my book, I didn’t have that many comments. However, I had two that I thought were very important. The famous wine dialogue between Miles and Maya, for the first two drafts only had Miles rhapsodizing on Pinot Noir, his favorite grape variety. My margin notes on the second draft suggested that maybe Maya should have a complementary speech. I didn’t write that speech, but it came in the third draft and is one of the great scenes in the film.

The other contribution was the ending. The first three drafts of the screenplay ended with Miles hearing a message from Maya on his answering machine. I complained, or remarked is more like it, how neither fish nor fowl that was. In the novel, Maya, somewhat shockingly, shows up at Jack’s wedding. Alexander thought that was too “Hollywood.” In the end, he met me halfway, with Miles returning to Buellton to see her—well, knock on her door. Alexander had complete control of the film—cast, final cut, everything.

Maya talks wine (Sideways)
“My margin notes on the second draft suggested that maybe Maya should have a complementary speech. My other contribution was the ending.”


JRM: Movies are seldom what the original author envisioned. How satisfied were you with the completed film?

RP: Very satisfied. Ecstatic, really. For example, the novel was written in first person, from the standpoint of Miles. That means, in the novel, I couldn’t go anywhere Miles didn’t go. In the movie, they could. But they didn’t. The film stays in the first person. We never journey off with Jack and Stephanie (nee Terra in the novel).

Also, the chapter structure of the novel was “Saturday,” “Sunday…” The movie maintained this chapter structure, utilizing title cards over black before the beginning of each day. It’s as if they filmed the novel.

Of course, some things had to be changed. Miles became a middle school teacher, whereas in the book he’s an out-of-work screenwriter hoping his novel will sell. Also, Sandra Oh—Stephanie in the film and Alexander’s wife in real life—changed a lot of things about her character so she would stand out more. She changed her name, her mode of transportation, added an interracial kid.


JRM: What effect did the film have on your book sales, your life, and your career in general—can you paint before-and-after pictures?

“Before the movie I was nobody. My life was complete shit. After the movie, suddenly everyone wanted something from me.”

RP: Before the movie I was nobody. My life was complete shit. When the book came out, my publisher did nothing. The book should have been heavily promoted. It wasn’t. It should have been in every wine tasting room on the Pacific Coast—hell, the world!—and it wasn’t. They did no publicity, nothing.

After the movie, things improved dramatically. The film’s success raised my profile as a writer, and suddenly everyone wanted something from me. They wanted me to write TV—which I’m doing now, by the way. They wanted me to write another novel, to do adaptations, even a TV show. I had four agents working for me, and they all wanted something they could capitalize on.

I chose to write a novel for a different publisher. They made my life a living hell, and that’s a long story. The short version is, I sold a novel based on a screenplay I’d written in ’93, called The Road Back. The script was optioned 5 years, but never made, so I was going to novelize it. I had trouble with the novelization and I got zero support from the publisher.

But—and this is where it gets complicated—I needed the mother/son story from The Road Back to do the Sideways sequel Vertical. The publisher agreed to let me do that, but they weren’t happy about it. Then things got ugly, at which point I found an investor, bought out my publishing contract and came out with Vertical under my own imprint in January 2011.


JRM: Many authors find that a successful adaptation brings them more money than they earn from the book itself. Would you say this is true of your situation?

“All told, I made less than $100,000 off the book itself—advance, foreign, everything. The day the movie went into production, I made $300,000 on the film side.”

Miles gets it right (Sideways)

RP: All told, I made less than $100,000 off the book itself—advance, foreign, everything. The day the movie went into production, I made $300,000 on the film side. There’s no question it raises your profile, that you have a lot of opportunities to do a lot more things. I was principally a screenwriter and indie filmmaker before becoming a novelist. And Sideways certainly opened doors.

But I’m still the same modest, non-materialistic guy I was before. To me, it was never about the money. It was always about the critical and commercial validation. And we got that in spades.


JRM: Being a screenwriter to start with, why did you decide to become a novelist—and to create Sideways as a novel rather than as a screenplay?

RP: I originally wrote it as a screenplay, but it didn’t work. Back then I was writing a short story in the first-person, from the standpoint of a character named Miles. It was at a wine tasting in Santa Monica. I got to the end of the short story, realized Jack could show up, and off they would go. I stood up from my computer in a rare moment of pure epiphany, and realized I had a novel. The first-person voice of Miles made all the difference.


JRM: Did you write the novel with the idea that it would—or could—become a movie?

RP: Yes, absolutely.


JRM: How did you first learn that the film based on your book had been nominated for five
Oscars, and what did that feel like?

RP: I was watching the announcements on TV at 6:00 a.m. when they come on. Five nominations, all in major categories! Of course I was beyond thrilled.


JRM: How did it feel when the screenplay won?

RP: Ecstatic.


JRM: Sideways was also nominated for five Golden Globes, and won two—best screenplay and best picture. Were you invited to the Golden Globes and to the Academy Awards?

Jack gets it wrong (Sideways)
“I was not invited to the Golden Globes. I was invited to the Oscars, but was seated in the middle tier, behind the cameras.”

RP: I was invited to Fox Searchlight’s Golden Globes party on the top floor of the Beverly Hilton, where the ceremony was held, but not to the actual awards. I was invited to the Oscars, but was given a seat at the last minute, in the middle tier behind the cameras, rather than with the Sideways nominees and their plus-ones and the Fox Searchlight brass.


JRM: Many of the people reading this will be book authors who intend to sell film rights, or to adapt the book themselves or with help and then sell the screenplay. Do you have any thoughts on the best route to pursue?

RP: More than likely, you shouldn’t be the one to adapt, because it’s very hard to adapt your own work. In many cases, it’s disastrous. Pure novelists are usually bad screenwriters, especially when adapting their own work. They tend to transcribe their novels, which is the biggest mistake you can make when adapting.

“More than likely, you shouldn’t be the one to adapt, because it’s very hard to adapt your own work. In many cases, it’s disastrous.”

To adapt well, you have to have the ability to pick and choose what to keep, and to be brutal in how you go about it—without defaming the source material. And that’s hard for a novelist to do with his own book. Probably nine out of ten novelists aren’t capable of writing a good screenplay, let alone adapting a novel—much less their own. It goes the other way, too: nine out of ten people writing screenplays couldn’t write a good novel.


JRM: For those new to film—any thoughts on the difference between writing a book and writing a screenplay?

RP: This would take too long to answer completely. They’re different animals. A good screenplay is really a novel imagined and then adapted without having written the novel. Writing a novel is different depending on the novel, of course. There are purely literary novelists that are just un-adaptable for the screen. Then there are authors like Elmore Leonard and John Grisham whose books all get optioned, and many made.

Writing a novel is harder because it’s longer. A good screenplay is not easy to write, but it’s easier to write, if you know what I mean. Fewer words. With montages, you can jump around. You can’t really do that in a novel, to generalize. I started writing novels to separate myself from the myriad screenwriters toiling away in the various Starbucks.


JRM: When, say, a first-time author signs a standard publisher’s contract, they sometimes fail to realize that they’re signing away rights to—or income from—film, multimedia, and merchandising sales that may be important down the road if Hollywood takes an interest. Was this an issue for you?

RP: Hopefully the lawyers take care of that stuff. Mine did.


JRM: Speaking of contracts—can you say what kind of deal you were able to negotiate on Sideways?

RP: It was $5,000 for the novel, plus 70 cents for every copy sold once the advance was earned out. Not much. For the adaptation, 3% of the budget, with a ceiling [maximum] and a floor [minimum]. Which came to $300,000 altogether, plus 2.5 worthless net points.


JRM: As both novelist and screenwriter, you know New York and L.A. What would you say are the most important things for a book author (or other creator or rights-holder) to know when pursuing a film adaptation?

RP: Before you write a book, be mindful of what a screenplay is—dialogue and action and compression of narrative time. And oh, yeah, you need a book that can be made into a movie.

“Before you write a book, be mindful of what a screenplay is—dialogue and action and compression of narrative time. And oh, yeah, you need a book that can be made into a movie.”

Miles does one thing well (Sideways)

On the business side, it depends on what kind of power you wield and how badly you need the money. Sure, there are directors or actors in a position of power, who you know might be completely wrong for your material. But, if they’re waving a fat check at you, I guess you have to decide between your work being vitiated for money, or sticking to some ethical code and holding out for someone who is right, maybe for a lot less money—and potentially risking that it will never sell. It’s a tough call, if you’re lucky enough to find yourself in that position.


JRM: What’s next for you—-and how are Vertical’s film prospects looking at the moment?

RP: The Vertical novel—the Sideways sequel—is my latest effort. The film sequel is out of my hands. Fox Searchlight owns the film rights to Miles and Jack in perpetuity. They’ll wait on Alexander Payne, but that could be a long time.



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