The Aftertaste of “Sideways”

Alexander Payne’s Oscar-winning movie turns 20 this year. Rex Pickett, who wrote the novel it’s based on, can’t stop writing sequels.

I’m not even sure how I stumbled across the story of screenwriter Rex Pickett and his experiences with the Sideways novel and film, which turned 20 this year. I just remember thinking, for a writer, this must have been one insane journey. To go from multiple rejections, to hitting bottom and researching camping gear, then suddenly getting a movie deal, and watching it be made into a classic award-winning film—it just seemed unbelievable. See what you think. This week’s post is the crazy, torturous, hilarious story of how the Sideways novel and film came to exist. Originally published in Alta Journal (link to full article below).

In early 1999, Brian Beery sent in his résumé to director Alexander Payne, who was fresh off the critically acclaimed film Election, starring Reese Witherspoon and based on the novel by Tom Perrotta. Payne hired Beery as an assistant in his production office at the Asahi building in Los Angeles. It was a dream job. He was already a huge fan of Election and Payne’s previous film Citizen Ruth.

Each week, Beery would make the trek to the corner of Wilshire and La Brea to meet with Payne. Beery had been acting since he was 12 and was studying screenwriting at UCLA; for Payne, he was tasked with managing the dreaded slush pile, a grinding but necessary cog in the creative process.

“It was about 150 books and screenplays and film ideas that had been submitted,” says Beery. “I would get 10 books and scripts. I’d go home, and then I’d come back the following week and share my thoughts and opinions about each one.”

Beery spent his weeks on the sofa, reading submissions that might match Payne’s tasteful, nuanced brand of humane satire. One heist comedy looked promising, reminding him of something the Coen brothers might do. Another seemed workable, a film noir project attached to Ashley Judd.

“But other than that, about 150 noes,” recalls Beery. “There was one about Bill Gates that they tried to say was a satire, but I didn’t think so at all. 10 Things I Hate About You was also in that pile. I didn’t like that. I didn’t think it would be his taste at all.”

Beery would handwrite a summary for each submission in a notebook and present his synopsis to Payne. It seemed an almost pointless exercise until one night at his apartment, Beery picked up an unpublished novel manuscript titled Sideways. As he read it, Beery was reminded of The Sun Also Rises. Young people traveling. The longing, the drinking. Being in love with someone, yet not being able to connect with them. Having to rebuild yourself emotionally after a devastating experience. The tale blew him away.

It was a simple story, a first-person narrative. Two friends take a road trip from Los Angeles to the Santa Ynez region for a little golf, some quality wine. One is an exuberant character actor who needs to blow off steam (read: sleep with some women) before his impending wedding; the other is depressed, a burned-out writer collecting rejections and obsessing about a prior relationship.

“Originally, it opens on Miles getting drunk at a wine-tasting event, and he sees his ex and has a panic attack and goes underneath the table,” remembers Beery. “I was really drawn in just from that moment. And then when he goes and steals money from his mother? I felt like I was reading something honest and real.” Beery was convinced Payne would find it interesting.

What Beery did not know was that the Sideways novel had been rejected, more than 100 times, by both Hollywood and the book publishing industry. Its author, a screenwriter named Rex Pickett, had some modest success with two indie feature screenplays earlier in the decade, which had been optioned but not made. His life was not turning out as he had hoped. He’d been let go as a writer for David Fincher’s big-budget Alien 3. His book-to-film agent had left the business. His wife divorced him. His mother was in assisted living. He was living in an apartment in Santa Monica with a roommate, subsisting on loans from family and friends and credit cards he’d been offered through the mail. In 1999, nobody needed Brian Beery more than Rex Pickett.

For the rest of the story, follow this link to Alta Journal.