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 It seemed an almost pointless exercise until one night at his apartment, Beery picked up an unpublished novel manuscript titled Sideways.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.
The story of Sideways had formulated some years earlier when Pickett frequented a Santa Monica tasting room called Epicurus, where boisterous and eccentric regulars took advantage of the multiple free pours. Pickett socialized with the crowd and sampled some fine wines.
Sometimes he drove to the Santa Ynez Valley to play golf on weekdays and to hit the tasting rooms. On one memorable trip, his road buddy was a film electrician named Roy Gittens, a gregarious guy who also loved wine. Gittens suggested to Pickett he should write about their tasting adventures. Pickett wrote a script with the don’t-do-drugs title Two Guys on Wine, using himself as the model for Miles and Gittens as the template for the character of Jack.
It didn’t sell.
Mostly that was because Pickett never sent it out as a submission and ended up writing a short story about the Epicurus tasting room called “The Bullpen.” Then he realized that it was actually the prologue to Two Guys on Wine and should be a novel instead.
It took him nine weeks to pound out a draft, opening with a scene set at the Epicurus tasting room. The first-person voice of Miles—dark, pessimistic, with occasional bursts of wit, and a genuine love of pinot noir—just flowed naturally. Pickett leaned on dialogue with minimal prose. And it wasn’t about aliens, or dinosaurs, or versions of Cameron Diaz’s hair gel, or whatever was selling at the time. It was about real guys in career slumps, struggling through the difficulties of their lives. And it was funny.
He finished it in 1999, and it took his book-to-film agent an unnerving four to six weeks to read it. Luckily, the agent was ecstatic. He had one caveat: change the title. Pickett dove back into the manuscript and found the word “sideways,” which was British slang for “drunk.” It was short, clever, and would one day look great on a marquee.
It didn’t sell.
One senior editor at a major publishing house was particularly heartless: “Sideways is nothing more than a glorified screenplay, and if it was made into a film it would stink to high heaven with the rot of Pickett’s writing.”
After a few months, Pickett’s agent stopped sending it to publishing houses. Submissions continued to movie people, but the rejections piled up. Sideways wasn’t clicking.
Pickett’s ex-wife, a producer and director, came to visit him during this period. She had read the draft.
“She came over, and—I’ll never forget—she sat on my porch, and she just hands me my manuscript,” Pickett says miming the act of handing over the pages. “She told me to burn it.”
“Burn it.” It’s a quote Pickett has repeated many times in interviews and in online essays. It’s a brutal comment, especially coming from your former spouse. Why keep sharing it over the decades? A good line is a good line.
“I don’t know what I’m doing next,” Pickett remembers thinking. “And in fact, at that point, I’m probably pretty much giving up on writing.”
Fortunately for Pickett, Beery loved it. Based on his enthusiastic recommendation, Payne took the manuscript of Sideways on the plane with him to the Edinburgh International Film Festival. On the flight home, he read the manuscript and as soon as he landed began making the calls that would completely upend Pickett’s life.
Meanwhile, the author was researching camping gear online, paranoid that he might lose his apartment. His roommate had gone on a weed and tequila bender and was bringing home sex workers, doing cocaine, and losing money in an investment con, something to do with Alaska natural gas leases, as roommates sometimes do.
One day, Pickett drove his beat-up Honda Accord to Baja Fresh for a burrito combo plate. His credit card was declined on a $6.99 order.
He went home that afternoon and found two messages on his answering machine. One from his agent and another from producer Michael London. Both were screaming with excitement. The camping gear could wait.
Meetings happened. The book was optioned. Pickett got some money. Trade publications ran front-page stories: “Payne Goes ‘Sideways.’ ” The manuscript went back to submissions. Surely, the movie buzz would prompt a sale of Pickett’s novel.
It didn’t sell. Until it did—in Japan.
The story of Sideways was finally going to be told, in book form in Asia and on film in the United States. There’s nothing like a Hollywood high, when everything seems to fall into place. Pickett’s phone was ringing again. At the 2000 Oscars, his ex-wife won a statue for Best Live Action Short, My Mother Dreams the Satan’s Disciples in New York, which he had written, and she thanked him from the stage. Pickett and Payne took a day trip up to the Santa Ynez Valley and tasted wines. This year was going to be very different.
But Payne soon called Pickett and told him he needed to put Sideways on hold. He was going to make a loose adaptation of Louis Begley’s About Schmidt first. Not to worry, though, Sideways is up next. (As an Easter egg teaser, Payne would include a background shot in About Schmidt of a movie theater marquee, displaying a one-word film title that fit perfectly: Sideways.)
Two years later, Payne invited Pickett and some others to dinner and handed over the first draft of the Sideways screenplay which he wrote with his partner Jim Taylor. After Pickett returned home, he couldn’t bear to look at it for hours. Eventually, he poured a glass of wine and started reading.
Immediately, Pickett realized how much they’d kept of his original story. The character of Miles Raymond was changed from a burned-out screenwriter to an English teacher struggling to get his first novel published. But they kept the point of view squarely on Miles; everything in both the book and the script was seen from his perspective. They kept the chapter structure and used most of the dialogue. They even resurrected the famous line, found in an earlier draft of the book, which is now in the Hollywood dialogue hall of fame: “I am not drinking any fucking merlot!”
They really honored it, thought Pickett. They could have gone off with other characters and invented more scenes, but they stayed close to the text and kept the narrative in the first person. As he’d done with his previous films Citizen Ruth and Election, Payne had extracted a meaningful yet hilarious story from the source material.
The novel finally found a U.S. publisher and came out in June 2004, five months before the film was released. The deal was not great: $5,000, paperback only, from St. Martin’s Press. The rollout was equally paltry. At one signing in San Francisco, five people showed up.
The movie premiered in September at the Toronto International Film Festival. Kirk Honeycutt, then chief film critic for the Hollywood Reporter, caught a morning press screening. He loved it so much, he begged for tickets to the premiere the following evening, where it received a standing ovation.
“The reviews on the day of the premiere were staggering,” says Honeycutt, coauthor of the book Sideways Uncorked: The Perfect Pairing of Film and Wine. “Nobody saw it coming. And that includes the filmmakers and the executives behind the film. It was a surprise to everybody. Alexander certainly thought it was going to be at best a modest hit.”
Honeycutt popped the metaphorical cork in his subsequent Sideways review: “This hysterically funny yet melancholy comedy about two guys adrift in the Southern California wine region has a beautiful structure, a buoyant bouquet of risky romance, a fine balance between its seemingly loose sequence of events and tight control of dramatic subtext, subtle undertones of the great character movies of the 1970s and a delicate though strong finish that fills one with hope for its most forlorn characters.”
While reviews were good, it was the word-of-mouth buzz that made the film a hit. An unlikely leading man, Paul Giamatti, fresh from the biopic American Splendor, completely inhabited the darkness of Miles while simultaneously showing us his heart. Sitcom actor Thomas Haden Church was a perfect choice for the party monster Jack, frisky and flirtatious yet dimly aware his career had tanked. Virginia Madsen shed her previous ’80s-babe reputation and stole the film with her portrayal of Maya, a waitress in a holding pattern. Sandra Oh brought the story alive as the feisty wine-pourer who falls for Jack, only to later unleash a well-deserved beatdown with her bike helmet. All of this wrapped up in some beautifully languid cinematography that showcased the Santa Ynez Valley and loitered on the grapes in the sun. Four broken souls brought together in a realistic story of painful life choices that everyone could identify with, elevated by the understated humor and restraint of Payne’s direction.
After opening on just four screens in October 2004, Sideways has gone on to gross $109,706,931 worldwide. It won awards from the Critic’s Choice to the Golden Globes, the Writers Guild, BAFTA, the Independent Spirit, and the Screen Actors Guild. In February 2005, Payne and Taylor accepted the Oscar for Best Adapted Screenplay, with Pickett watching from the balcony.
Sideways soon entered the zeitgeist. People were drinking more pinot noir, inspired by Miles’s character-revealing monologue about the varietal, and making jokes about merlot. Restaurants and tasting rooms of sleepy Santa Ynez crowded with tourists looking for the film’s locations.
Pickett was doing pretty well too. He was fielding offers from TV, academia, and wine organizations. The timing for a sequel couldn’t have been more perfect. He discussed it with his agents, but he didn’t own the film rights to the characters—the characters that were based on himself and his friend—even though they also appeared in his novel. Fox Searchlight owned the characters, and it didn’t want a sequel film. But fortunately for Pickett, his contract provided a loophole. The studio ownership did not apply to books and other mediums.
After an unrelated book deal with Knopf was canceled, Pickett decided to write the sequel just as a novel, eventually titled Sideways: Oregon.
But nobody in Hollywood seems interested in another chapter of the Sideways universe. Payne was unavailable for this story, but Honeycutt had asked the director and others about the possibility of a second Sideways movie.
“There is no desire that I could detect on the part of any of the people on the film side to do a sequel,” he says. “And I’ve talked to a lot of people. Paul Giamatti, in our conversation, said he had no interest whatsoever in doing a sequel. Nor can anybody figure out where it would go.”
Among other reasons, says Pickett, Giamatti was getting tired of people sending him bottles of merlot at restaurants just to see his reaction.
But Sideways had resonated deeply with audiences. This was Pickett’s story. He wasn’t going to be a one-hit wonder like Harper Lee or John Kennedy Toole. He wasn’t going to let Miles and Jack die, so to speak, on the vine.
He adapted Sideways for the stage, which premiered in 2012 at the Ruskin Group Theatre in Santa Monica. The play moved to a longer run at the La Jolla Playhouse, and then toured. In 2023, it sold out an 11-show run at a 250-seat theater in Riga, Latvia. Pickett also wrote the book and lyrics for a musical version and released its original cast recording in 2023.
Representatives for wine regions around the world approached Pickett in the hopes of having his visit lead to another hit movie set in their vineyards. He accepted offers to visit Chile and New Zealand and wrote more adventures for Miles. The boutique publisher Blackstone, in Ashland, Oregon, signed on to produce hardback editions of the Sideways stories: Sideways: Oregon, Sideways: Chile, and Sideways: New Zealand. The company has also published Pickett’s recent thriller, The Archivist.
As Pickett has tried to squeeze every last drop out of his creation, including the launch of Sideways wines, the principles behind the Sideways phenomenon have all moved on. Paul Giamatti, Sandra Oh, and the rest of the cast continue to work regularly. Michael London produced Milk, The Informant!, and Trumbo. Payne’s most recent film, The Holdovers, won 134 awards, including a Best Supporting Actress Oscar for Da’Vine Joy Randolph.
Pickett and I met to discuss the 20th anniversary of Sideways at the tasting room of Vintner’s Collective, a showcase of boutique wineries located in a historic landmark stone building in downtown Napa. He’s taller than I imagined and certainly bears no resemblance to the balding, jowly Giamatti. He’s wearing a black T-shirt, jeans, and Ray-Bans; his sandy brown hair is gray at the temples. He just turned 67 this year, but he looks significantly younger.
Since he no longer drinks (“I’m more of a sip-and-spit guy,” he says), we grab seats upstairs away from the bar.
The tasting room is three blocks from his house. Every time he drops in he signs books, which are always for sale here. He tells me that he’s working on Sideways 20, with more titles on the horizon. Throughout 2024, he’s been the special guest at Sideways anniversary screenings, dinners, and tastings.
As we talk, I start to feel like I’m having a conversation with Miles. All writers complain—especially ones who’ve had a taste of Hollywood—but Pickett is really good at it. Literary agents are pushy. The producer claimed he came up with the title. I wrote the fucking bible, and I have every right to speak out about it. New Zealand screwed me over. I did one thing for HBO, and they just drove me crazy in development. If there’s a horse in the movie, I won’t see it. Like Miles, he’s dark but funny.
I ask why Sideways has endured.
“It’s really Miles,” he says. “Miles is my alter ego, obviously. It’s a funny movie. At that top layer, it’s kind of a bawdy comedy; you can watch it as that. But it’s [the] complex relationships, really, if you think about it. Not so much intellectually complex, but emotionally complex relationships. It’s really Miles—me—staring into the abyss of failure. That’s how I see it.”
This may also be why no one in Hollywood or mainstream publishing wants to revisit Miles’s world. Their lack of interest has pushed Pickett to nanofocus on the one project that clicked. The book poured out of a painful, personal time in Pickett’s life that he’s clearly still processing.
“I didn’t sit down and say, OK, I’m going to write about this universal theme of going through this,” he says. “That’s just where I was at. I was clinging with my fingertips to this novel.”
When I think about why the movie version was so successful, as opposed to the novel and its sequels, I find myself remembering Virginia Madsen’s key moment, a monologue that more or less earned her an Oscar nomination. Maya and Miles are on what amounts to their first date, talking on Maya’s porch about why they love wine, and she tells him how she likes to think “about the life of wine, how it’s a living thing.”
“I like to think about what was going on the year the grapes were growing, how the sun was shining that summer or if it rained, what the weather was like,” she tells him. “I think about all those people who tended and picked the grapes, and if it’s an old wine, how many of them must be dead by now. I love how wine continues to evolve, how every time I open a bottle it’s going to taste different than if I had opened it on any other day. Because a bottle of wine is actually alive, it’s constantly evolving and gaining complexity. That is, until it peaks…and begins its steady, inevitable decline.”
Payne holds Madsen in the frame looking right at the camera—at Miles, at the audience. The director was married to co-star Sandra Oh during the production of Sideways, but it’s Madsen around whom he constructed this gorgeous scene. It’s beautiful and moving, the perfect complement to Miles’s one true passion. Will they get together? We have no idea, but we want to keep watching. She pauses and ends with, “And it tastes so fucking good.”
The scene was written by Payne and Taylor; it doesn’t exist in the original book. And it doesn’t come from Miles’s perspective. In a sense, it’s the purest collaborative moment by the writers, actors, director, producers, and crew. It’s not Pickett’s, but it never would have existed without him in the mix.
For film buffs, the Writers Guild of America’s list of 101 Greatest Screenplays is a vaunted ranking of cinematic storytellers. Each entry mentions the movie’s screenwriters as well as the authors of its source material. Rex Pickett’s name is enshrined on that list at No. 90, holding a place alongside Raymond Chandler, Billy Wilder, Robert Towne, Ben Hecht. As legacies go, you can’t do much better. Pickett may be treading water in a pinot-colored purgatory, but even he has to admit that his 2004 California vintage has aged well.•
Jack Boulware runs the newsletter What Jack Boulware Fails to Realize. He was a cofounder and an executive director of San Francisco’s Litquake literary festival. He’s currently working on a novel based on his experiences as a travel journalist. He lives in West Marin.
