Education and early career Pickett was born at
Castle Air Force Base in
Merced, California, and grew up in
San Diego. In 1998 he wrote the screenplay for ''
My Mother Dreams the Satan's Disciples in New York,'' which went on to win the
Academy Award for Best Live Action Short in 1999.
Novels and Sideways In the 1990s, Pickett began writing novels and his first, a mystery titled
La Purisima, didn't sell. His second was
Sideways. Completed in 1999, the novel was submitted to both publishers and film production companies. After 18 rejection letters from publishers, Pickett's agent pulled it from submission. Film production companies also passed. In late 1999, nearly a year after it had been written, one of the submissions by Pickett's agent, Jess Taylor, at Endeavor, went to Alexander Payne's agent, David Lonner at the same agency. Payne's assistant, Brian Beery, read it then passed it to Payne who immediately optioned it. Shortly after Payne optioned
Sideways it was greenlit by
Artisan Entertainment. Pickett's agent at Curtis Brown went back out to publishers in a mass submission but it was again rejected. Eventually, Payne would put
Sideways on hold and go off to make
About Schmidt. In early 2003, Payne, fresh from the success of
About Schmidt, returned his attention to
Sideways. The project was
greenlit by
Fox Searchlight, who gained control of it from Artisan in July 2003 and a start date announced for late September. After more than 100 rejection letters, Pickett's new agent at Trident Media Group went back out with his still unpublished novel and ended up selling it in a fire sale to
St. Martin's Press for $5,000. It was published in June 2004, four months before the film was released.
Sideways the film was released on October 22, 2004. It went on to win over 350 awards from various critics and awards organizations, including 6 Broadcast Film Critics Association Awards, 5 New York Film Critics Circle Awards, 5 Los Angeles Film Critics Association Awards, 6 Indie Spirit Awards, 2
Golden Globes, et al. It was nominated for five
Academy Awards, winning in the Best Adapted Screenplay category. The film had an impact on the sales of two types of California wine, driving
Pinot noir sales and decreasing
Merlot, the grape variety the main character, Miles, expressed hatred for. In 2011, Pickett released a sequel to
Sideways, titled
Vertical. That same year it won the gold medal for Popular Fiction from the Independent Publisher Book Awards. In 2012 Pickett staged a play version of his novel
Sideways at the Ruskin Group Theater in
Santa Monica, California. It ran for six months and a production was later staged at the
La Jolla Playhouse under the direction of
Des McAnuff. Pickett spent a year traveling in
Chile,
New York, and
Costa Rica before completing
Sideways 3 Chile, set in the Chilean wine world. It was published in 2015. In 2024 a fourth novel in the series was released,
Sideways New Zealand. ==Stage and musical adaptions==