Leavitt's screenwriting career began in 1996 when he wrote Sunchaser.
He wrote the screen adaptation of the Rodman Philbrick novel Freak the Mighty for the screen in 1998. The Mighty starred Sharon Stone, Gena Rowlands, Harry Dean Stanton, Kieran Culkin and Elden Henson. The film received two Golden Globe Awards for Best Supporting Actress (Sharon Stone) and Best Original Song ("The Mighty").
After writing the script for the 2001 film K-PAX, Leavitt was hired by Warner Bros. in February 2004 to rewrite an early draft of the film Blood Diamond, then titled Okavango. The story had been stuck in "development hell" at the studio for years before producers Paula Weinstein and Gillian Gorfil finally decided on the story of a Sierra Leonean farmer caught up in the conflict between a White Zimbabwean smuggler and the local diamond mining organization.

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