Pickett graduated summa cum laude from the University of California in San Diego. After a brief stint at the University of Southern California graduate film school, he left and, with his then wife Barbara Schock, wrote, directed and edited two independent feature films: California Without End ($60K budget) and From Hollywood to Deadwood ($650K budget). The former was sold to Bavarian Radio Television in Germany and the latter was bought and theatrically released by Island Pictures.
Pickett then returned to writing, optioning original scripts, adapting novels and doing rewrites for hire. A short he wrote, My Mother Dreams the Satan's Disciples in New York, was directed by Schock as her American Film Institute thesis project. The film was awarded the 2000 Academy Award for Best Live Action Short.
Pickett worked with David Fincher on the screenplay for Alien 3, but his script was ultimately rejected by producers David Giler and Walter Hill.
Pickett's greatest success came with his novel Sideways. Though originally rejected by 15 different publishers in three submissions, to date Sideways has sold over 150,000 copies in the English-language edition, and has been translated into 11 other languages. The film version, directed by the critically-acclaimed Alexander Payne, won over 350 awards in major categories from various critics and awards organizations, including five New York Film Critics awards, including best picture, screenplay, and director; five L.A. Film Critics awards, again all in major categories; six Indie Spirit awards, for best picture, screenplay, supporting actor and actress, and best actor; two Golden Globe awards, for best picture musical or comedy, and best screenplay; five Broadcast Critics awards; and the SAG award for best ensemble cast. Pickett also figures on-screen: In the scene in which Miles (played by Paul Giamatti) hits the ball at the other golfers, it was actually Pickett who performed the shot, due to Giamatti's poor golf abilities. Sideways was also made into a Japanese film, Saidoweizu.
Pickett is currently represented by Trident Media on the publishing front, Endeavor (now WME) on the film literary front, and the Joel Gotler Agency on the book-to-film front. He is currently under contract with Alfred A. Knopf (Random House's literary division) for his next novel, a sequel of sorts to Sideways, tentatively titled Shambolic.