Cyphers's first feature film was the 1974 movie Truck Turner, and he first worked with Carpenter in the 1976 action film Assault on Precinct 13, in which he played Starker, one of the ill-fated police officers gunned down by gang members.
He later appeared as Sheriff Leigh Brackett in the 1978 hit horror movie Halloween. Cyphers worked with Carpenter two years later, playing Dan O'Bannon in The Fog, a 1980 horror film which also starred Tom Atkins, Cyphers's fellow Halloween cast member Jamie Lee Curtis, his Assault on Precinct 13 co-star Darwin Joston, and Nancy Kyes, who worked with Cyphers in both Assault on Precinct 13 and Halloween. He then played the Secretary of State in Carpenter's popular 1981 film Escape from New York, in which he appeared with Atkins and Halloween actress Nancy Stephens. He reprised the role of Sheriff Brackett in Halloween II.
In 2005, he appeared in the movie Dead Calling, and in 2007 he was set to appear in Ethan Dettenmaier's unreleased film, Sin-Jin Smyth, and in the film Methodic in a role which paid homage to his character in Halloween.

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