Author and Alumnus Rex Pickett Brings “Sideways” to La Jolla Playhouse

Award-winning director Des McAnuff helms new stage version of Pickett’s iconic road trip novel

“If anyone orders Merlot, I’m leaving.”

That line of dialogue is familiar to thousands of fans of “Sideways,” a novel that spawned an Oscar-winning movie, gaining a cult following since the iconic road trip story hit bookstores and theaters in 2004. The plot follows two middle-aged male friends – Miles and Jack – as they make their way through California wine country and meet two women who become potential romantic interests. Thanks to the popularity of the novel by Rex Pickett and the film by Alexander Payne, sales of Pinot Noir have skyrocketed and Merlot’s fortunes have tumbled.

Nearly a decade later, author and UC San Diego alumnus Pickett has a new project that promises to tap his fan base and create another hoped-for commercial and artistic success. Pickett is collaborating with Tony Award-winning director Des McAnuff to launch the stage version of his novel “Sideways” at the Tony Award-winning La Jolla Playhouse, located in UC San Diego’s Theatre District.

For Pickett, whose home base has been Santa Monica, except when on wine-discovery forays to Chile and other international locales, this play is a homecoming of sorts. He graduated summa cum laude in 1976 from UC San Diego with a special projects major; his diploma reading: “Specializing in Contemporary Literary and Film Criticism and Creative Writing.”

“Manny Farber was the greatest influence in my life,” said Pickett of the late Farber, an influential and iconoclastic film critic, abstract painter and UC San Diego Professor Emeritus of Visual Arts. “I always wanted to make films, so after graduation I moved to LA to attend USC graduate film school.”

He left film school after one year when the opportunity to make an independent feature film arose. Pickett spent the better part of the 80s making two films; one had a theatrical release in 1989 – “From Hollywood to Deadwood.”

But filmmaking took a toll.

“It took eight years out of my life, and my wife, who produced the films, is now, well, my ex-wife, though we remain on great terms,” he said. “By the 90s, I needed a change, so I started sojourning in California’s Santa Ynez Valley. It was an inexpensive, and uncrowded, haven with wineries, and, ultimately, became the setting for ‘Sideways.’”

There Pickett found some semblance of solace, peace and friends, bivouacking at the Days Inn Windmill in Buellton, and eating at the Hitching Post, a popular spot for local residents. Both played a role in Miles and Jack’s “Sideways” journey.

Creativity returned, and in 1999, Pickett started writing a novel loosely based on his life and time spent in the Santa Ynez Valley.

“The novel underscores the foibles and hopes and dreams of very relatable characters amidst the romantic backdrop of this little-known wine region,” he explained. “There is a verisimilitude to the characters – mid-life crises and relationships – there were just things I was going through at the time. I bared my soul through the characters; I am basically the Miles character. My agent loved it. Others were less kind.”

Rex Pickett. Photos by Erika Johnson/University Communications

Although an experienced screenwriter, Pickett faced difficulty in getting “Sideways” published. “No one wanted the novel,” he said. “The publishing world hated it, and voiced their detestation in no uncertain terms. Hollywood was just as clueless.”

It wasn’t until Alexander Payne discovered it on a pile of manuscripts and decided to option it and, eventually, turn it into a movie that it was finally published in 2004. The resultant film went on to win more than 350 awards from various critics and awards organizations. The screenplay of his novel, which won the 2005 Oscar, is enshrined in the Writers Guild of America Theater as one of the 101 Greatest Screenplays of All Time.

Although his novel became a movie that is still hugely popular, fame and fortune didn’t follow Pickett for long after the its critically-acclaimed release. Another decade brought a sequel – “Vertical” – but little else, until the author decided to turn “Sideways” into a stage play. “Sideways – The Play” opened May 18, 2012 at the non-Equity Ruskin Group Theatre, a small 50-seat theater in Santa Monica. Though in a developmental version, it was an instant smash.

“We knew, because of the colossal fan base of the movie, that it had huge potential,” Pickett said. “Three performances a week, we sold out. I was feeling confident again. It was electrifying to hear the audience’s laughter; it’s palpable, it’s a dopamine rush. Writing a play has been one of the most rewarding creative experiences of my life.”

“With this small theater success, I got to thinking that I should try to connect with Des McAnuff – I had met him briefly a long time ago and I knew that he, with a lot of support, had put La Jolla Playhouse on the map in the 80s. Armed only with the Internet, and without leaving my couch, I discovered that Des was now the artistic director at the Stratford Theater in Ontario, Canada. I remember the day exactly because it was my birthday, July 9^th.He got back to me with alacrity.

“As a huge fan of the Alexander Payne film, Des loved the play because he thought it really stood on its own, separate and apart from the movie. And that was his main motivation for deciding to do it. I was ecstatic,” Pickett said.

Fast forward to this coming July when playgoers will have an opportunity to see the newest version of “Sideways,” an honest and touching comedy with more characters, added scenes and a richer and more emotionally complex storyline than the movie or previous stage play as a result of the collaboration between Pickett and Playhouse Director Emeritus McAnuff (“Jersey Boys,” “Yoshimi Battles the Pink Robots”).

Rex Pickett.

Pickett added, “Des, I think, saw the theatrical potential in the play of my novel, which it’s a pure distillation of, because of the worldwide recognition of the movie. But I don’t think he would have been interested in the play if it hadn’t brought elements that built on the movie and burrowed down deeper into the novel. This serendipitous synchronicity with La Jolla Playhouse – one of the great regional theaters in the country – was, for me, like going from sandlot ball to Yankee Stadium in one transfer.”

In addition to alumnus Rex Pickett, the “Sideways” connection with UC San Diego also includes M.F.A. graduate and Playhouse veteran Zöe Chao playing the role of Terra, and Robert Brill, a graduate of UC San Diego’s department of theatre and dance, who is the scenic designer. A Tony Award-nominated set designer, Brill is La Jolla Playhouse’s inaugural artist-in-residence.

Pickett is understandably excited about the debut of “Sideways” at the Playhouse, which runs July 16 - August 18 in the Sheila and Hughes Potiker Theatre. He is also honored that UC San Diego Library’s Mandeville Special Collections Library has become the repository for his recently donated personal archive – manuscripts, screenplays, drafts of novels, journals, photographs and films. The collection debut should be of interest to his more than 42,400 Twitter followers (@RexPickett).

Today, Pickett’s life is back on track – he’s happy and living in La Jolla. “It’s all about the second act,” he mused. “I’ve come full circle, returning to my UC San Diego roots where the inspiration to become who I ultimately became took hold.”