Directing
Holland's directorial debut came in 1985 with the vampire horror film Fright 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 in 1988 titled Fright Night Part 2, and a 2011 remake, Fright Night starring Colin Farrell and Anton Yelchin. That remake also had its own sequel, Fright Night 2: New Blood, which was released in 2013. Holland was not involved in any of the sequels or the remake.
After Fright Night Part 2 was released in 1988 without Holland's involvement, Holland and star Roddy McDowall began discussing a potential third film. McDowall set up a meeting with José Menendez, the head of Carolco Pictures subsidiary Live Entertainment, who had acquired the Fright Night rights. However, before the meeting could take place, Menendez and his wife were murdered by their sons on August 20, 1989, ending all prospects for a direct sequel. Holland remained friends with McDowall until the actor's death in 1998.
On October 28, 2020, Holland confirmed that he is writing a direct sequel to the original Fright Night titled Fright Night: Resurrection and that his sequel would ignore the 1988 sequel and be a proper sequel to his 1985 film.
In June 2024, Holland participated in a Fright Night 40th Anniversary Table Read Podcast, a full cast reunion featuring Chris Sarandon, William Ragsdale, Amanda Bearse, Stephen Geoffreys, and Jonathan Stark, with Mark Hamill reading the late Roddy McDowall's role of Peter Vincent. In October 2025, the prequel novel Fright Night: Hellbound by Michael Harbron was published in collaboration with Holland.
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.
Holland directed three episodes of the HBO horror anthology series Tales from the Crypt: "Lover Come Hack to Me" (Season 1, Episode 5, 1989), written by Michael McDowell; "Four-Sided Triangle" (Season 2, Episode 9, 1990), co-written by Holland and featuring Patricia Arquette; and "King of the Road" (Season 4, Episode 9, 1992), written by Randall Jahnson and starring a then-unknown Brad Pitt. Holland recalled that upon meeting Pitt during casting, he saw "a movie star booming" in Pitt's presence.
He returned to television films with The Stranger Within.
Holland wrote and directed a 1995 ABC miniseries adaptation of the Stephen King novella "The Langoliers". The production was shot on 16mm film to reduce costs. King himself made a cameo appearance as a pharmacist, and Holland also appeared in a small role. The collaboration came about because King was a fan of both Fright Night and Child's Play, and producer Richard P. Rubinstein connected them.
Holland co-wrote (with Michael McDowell) and directed Thinner (1996), adapted from King's novel of the same name. The project had spent over a decade in development hell, with Holland stating it had been "turned down by almost every director in Hollywood" due to its bleak ending. Holland's son Josh Holland appeared in the film as Frank Spurton.
In 2007, Holland directed the episode "We All Scream for Ice Cream" for the Showtime anthology series Masters of Horror (Season 2, Episode 10), adapted by David J. Schow from a short story by John Farris. The episode starred William Forsythe and marked Holland's return to directing after an eleven-year hiatus following Thinner.
In 2012, Holland signed on to adapt King's short story "The Ten O'Clock People" from the collection Nightmares and Dreamscapes as a feature film. The project went through several casting iterations and location changes over multiple years before ultimately stalling in development.