In 1980, Bill directed his first film, My Bodyguard. From there he went on to direct Six Weeks (1982), Five Corners (1987), Crazy People (1990), A Home of Our Own (1993), Untamed Heart (1993), Flyboys (2006) which Bill claims was one of the first features shot entirely with digital cameras. For television, Bill directed Truman Capote's One Christmas (1994), Harlan County War (2000), and Pictures of Hollis Woods (2007), among others.