During the late 1950s, Milligan became involved in the nascent
off-off-Broadway theater movement where he mounted productions of plays by
Lord Dunsany and
Jean Genet at the
Caffe Cino, a small Greenwich Village coffeehouse that served as a hothouse for rising theater talent like
Lanford Wilson,
Tom Eyen and
John Guare. Milligan also became involved with directing low-key theater productions at the
La MaMa Experimental Theatre Club. During this period, he operated and designed for a clothing boutique named Ad Lib and used his dressmaking skills to costume many theatrical productions. In the early 1960s, Milligan began making movies. He met some of the actors for his early movies at Caffe Cino. His first released movie was a 30-minute black-and-white 16 mm short drama titled
Vapors (1965). The movie, set on one Friday evening in the
St. Mark's Baths, a
gay bathhouse for men, portrays an emotionally awkward and unconsummated meeting between two strangers. Milligan was later employed by producers of
exploitation films, particularly William Mishkin, to direct softcore
sexploitation and horror features, many featuring actors known from the off-off Broadway theater community. Most of his early exploitation movie fell into the genre of morality play. Milligan's plays and movies explored topics of transgression and punishment, dysfunctional family relationships, repressed sexuality, homosexuality and physical deformity, and include such titles as
Depraved! (1967),
The Naked Witch (1967),
The Promiscuous Sex (1967),
The Degenerates (1967),
The Filthy Five (1969),
Gutter Trash (1969),
The Ghastly Ones (1968),
Seeds of Sin (1968),
Fleshpot on 42nd Street (1973),
The Rats Are Coming! The Werewolves Are Here! (1973), and
Guru, the Mad Monk (1970). Most of Milligan's early works are currently considered
lost films. In 1966, Milligan set up his residence in a Victorian-era mansion located in
St. George, Staten Island, within a mile walking distance of the
Staten Island Ferry. The house soon became what he dubbed "Hollywood Central," where he filmed several of his movies. Milligan wrote, directed, built sets and sewed costumes for nearly all of his movies. His usual "stock company" often was supplemented by Staten Island locals. Milligan's early movies were shot with a single hand-held 16-millimeter
Auricon sound-on-film news camera. This technique was inspired by
Andy Warhol and allowed Milligan to move the camera around at will, at times punctuating violent scenes with his "swirl camera" technique through which he would spin the camera and point it to the ground. Often working with budgets under $10,000, his movies feature very tight framing that helped cover his very low budgets, particularly in the case of the period pieces that were most of his horror movies. His ability to make movies with such low budgets is why Mishkin often hired him and Mishkin's influence on the
42nd Street grindhouse circuit meant that Milligan's pictures played there often. Milligan filmed all of his movies on short ends; using old and unused leftover film reels of 16 mm and later 35mm film that he acquired through various means from other film sets as a means to keep production costs down. In 1968, Milligan began to make horror movies featuring gore effects with
The Ghastly Ones, a 19th-century period piece and his first color movie, produced by JER and titled by Sam Sherman. In 1969, he made his next horror movie, a medieval period piece titled
Torture Dungeon, after which he moved to London, England to make movies there after having made a deal with producer Leslie Elliot. After directing the exploitation drama
Nightbirds in London, his partnership with Elliot collapsed as he was working on
The Body Beneath. Milligan then teamed with William Mishkin again where Mishkin produced and Milligan directed three more 19th-century period piece British horror pictures:
Bloodthirsty Butchers,
The Man With Two Heads, and
The Rats Are Coming. The Werewolves Are Here (all shot in 1969). Milligan returned to
Staten Island in 1970. On his return to New York, Milligan wrote and directed another medieval period piece titled
Guru the Mad Monk, which was shot for the first time with a 35mm
Arriflex camera and filmed entirely inside the St. Peter's Episcopal Church in Chelsea, Manhattan. This movie was released in December 1970 on a double feature with
The Body Beneath. Through the next years, Mishkin released Milligan's British-made pictures, some with additional scenes shot in New York.
The Rats Are Coming! The Werewolves Are Here! was one of Mishkin's movies in which he had Milligan insert new killer rat scenes shot in New York, mostly at his new Staten Island house on Corson Street where Milligan lived during that time and filmed another horror period piece there in 1973, titled
Blood. After directing the 1972 sexploitation drama
Fleshpot on 42nd Street, Milligan's output was restricted mostly to gory horror movies as he moved to the southern tip of
Staten Island in the
Tottenville neighborhood where he lived in and owned and operated a dilapidated hotel located at the corner end of Main Street and Ellis Street right next to the southern end of
Staten Island Railway (currently an Italian-themed restaurant named ''Vincent Angelina's Ristorante
). On October 27, 1977, Milligan moved into 335 West 39th Street in Manhattan (a four-story building purchased for $50,000 by Milligan and stockholders), where he founded and ran the Troupe Theatre, an off-off Broadway venue above which he lived in a third-floor loft until he left New York City for good in March 1985. He moved to Los Angeles, where he briefly owned a dress shop on Highland Boulevard from late 1985 to early 1986. Milligan then directed three more independently produced horror movies in 1987 and 1988, which included Monstrosity
, The Weirdo
, and Surgikill'' as well as operated another theater and production company, called Troupe West, which ran until early 1990. In his non-fiction book about the horror genre titled
Danse Macabre,
Stephen King gives a short assessment of one of Milligan's movies: "
The Ghastly Ones is the work of morons with cameras." Milligan developed a reputation as a maker of awful horror movies, featuring
Herschell Gordon Lewis-type gore effects, both of which combined to give him a reputation as one of the worst directors of all time. The re-discovery of
Fleshpot on 42nd Street—generally regarded to be his best work—in the 1990s by the Seattle-based video company
Something Weird Video and the release of his biography in 2001 has made more widely known his theatrical background and the context to his work. Despite his modern-day recognition, most of Milligan's exploitation movies during the 1960s remain unseen because the prints were lost. ==Personal life==