Redwing was one of the top gun, knife, tomahawk, and whip instructors in Hollywood. After claiming that he began in films in Cecil B. DeMille’s 1931 "The Squaw Man" (although no cast list shows that he acted in that movie), Redwing soon became a gun-handling coach to Alan Ladd, Ronald Reagan, Burt Lancaster, Glenn Ford, Richard Widmark, Anthony Quinn, Charlton Heston, Dean Martin, Fred MacMurray and many other actors. He performed Alan Ladd's fancy gunspinning seen in the film "Shane" during the climatic showdown.