Holland made his screenwriting debut with the 1978 made-for-television filmThe Initiation of Sarah. He made his feature film writing debut in 1982, adapting the Edward Levy novel The Beast Within into the film of the same name. That same year, he wrote the Class of 1984, an urban thriller film centered on juvenile delinquency and punk subculture. The film proved controversial upon release and was heavily censored in the United Kingdom and outright banned in other countries. It has since become a cult classic. Holland was hired by Universal Pictures to write a sequel to the 1960 Alfred Hitchcock film Psycho, which since its initial release had been acclaimed as not only a seminal and iconic horror film, but one of the greatest films of all time. Lead actorAnthony Perkins, who had previously displayed apprehension at appearing in a sequel, agreed to do the film after being impressed by Holland's screenplay. The film, directed by Richard Franklin and co-starring Meg Tilly, Robert Loggia, and Dennis Franz, opened at No. 2 at the box office and went on to gross $34 million. Holland re-teamed with director Franklin the following year on his next film, Cloak & Dagger. Unlike their previous film, Cloak & Dagger was a spy film aimed at a younger audience, and starring Henry Thomas of E.T. the Extra-Terrestrial in its leading role. Despite positive critical reviews, the film was a financial failure, grossing $9,719,952 off of a 13 million dollar production budget.
Directing
Holland's directorial debut came in 1985 with the vampire horror filmFright Night. Holland first conceived of the premise during the writing of Cloak & Dagger, of a horror film fan who learns that his neighbor is a vampire. He chose to direct the film himself after being disappointed with Michael Winner's direction of his screenplay Scream for Help. The film was both financial and critical success, earning a rave review from Roger Ebert who wrote "Fright Night is not a distinguished movie, but it has a lot of fun being undistinguished." The film spawned a sequel, and a 2011 remake starring Colin Farrell and Anton Yelchin. In 1988, Holland directed the film Child's Play, which received positive reviews from Ebert and Leonard Maltin, spawned a long-running franchise consisting of six sequels, and helped elevate its antagonist Chucky to a pop culture icon. He directed three episodes of the horror anthology seriesTales from the Crypt, and returned to television films with The Stranger Within. He wrote and directed a 1996 ABC miniseries adaptation of the Stephen King novella The Langoliers, and the following year adapted King's novel Thinner into a film of the same name.
He and David Chackler founded the horror film company Dead Rabbit Films. Their first feature film was the remake of Fright Night. Holland is also reportedly scheduled to be writing and directing a feature-length anthology of horror shorts titled Twisted Tales.