[1][2] Pressfield was an advertising copywriter, schoolteacher, tractor-trailer driver, bartender, oilfield roustabout, attendant in a mental hospital, fruit-picker in Washington state, and screenwriter.

[2] Pressfield's first book, The Legend of Bagger Vance, which was loosely based on the Bhagavad Gita, was published in 1995, and was made into a 2000 film of the same name directed by Robert Redford and starring Will Smith, Charlize Theron, and Matt Damon.

[8] Prior to publishing his first original works of fiction, Pressfield wrote several Hollywood screenplays including 1986's King Kong Lives, 1988's Above the Law starring Steven Seagal and directed by Andrew Davis, 1992's Freejack, a work of science fiction starring Emilio Estevez, Mick Jagger, and Anthony Hopkins, and 1993's Joshua Tree (a.k.a.

Joshua Tree was directed by Academy Award and Bafta winning stuntman Vic Armstrong.

His novel The Legend of Bagger Vance was made into a 2000 film starring Matt Damon as the golf pro and Will Smith as his spiritual guide and was widely criticized for its use of the "Magical Negro" as a plot device.