He made his directorial debut with My Bodyguard (1980) and directed movies Six Weeks (1982), Five Corners (1987), Crazy People (1990), Untamed Heart (1993), and Flyboys (2006).

Bill began his career as an actor in the 1960s, first appearing on screen as Frank Sinatra's ingenuous younger brother in Come Blow Your Horn (1963).

Other acting credits include Marriage on the Rocks (1965), None but the Brave (1965), You're a Big Boy Now (1966), Never a Dull Moment (1968), How to Steal the World (1968), Ice Station Zebra (1968), Castle Keep (1969), Flap (1970), Shampoo (1975), Are You in the House Alone?

Bill continued to act in television movies, miniseries, and guest spots, though with decreasing frequency as he segued into directing.

He was featured on an ABC movie titled Haunts of the Very Rich (1972), appeared in the 1977 miniseries Washington: Behind Closed Doors, and the drama anthology series as the narrator What Really Happened to the Class of '65?.

He went on to direct Six Weeks (1982), Five Corners (1987), Crazy People (1990), A Home of Our Own (1993), Untamed Heart (1993), and Flyboys (2006), which Bill claims was one of the early features shot entirely with digital cameras.