During the first few years of his career, only a handful of cassette-only releases were available, including those by Sound of Pig, Controlled Bleeding, Merzbow, Illusion of Safety and If, Bwana.
In 1988 a long 8 minute track by Greif called The Rift In The Earth was selected to appear on the Tellus Audio Cassette Magazine issue #20 Media Myth, which brought further international attention to his work.
Also released was location recordings from Papua New Guinea which featured not only indigenous music but folk stories, theater and a church meeting in Pidgin English.
Shortly after this release, Greif teamed up with Mikhail Bohonus of WarWorld to form Static Effect, who performed improvisational music.
In 1990 Greif had begun work on his most ambitious project to date: a 6-hour musical and textural setting for Lewis Carroll's Alice in Wonderland.
About this same time Greif began a project with Dan Burke of Illusion of Safety, which after a year of collaborating by exchanging sequences, sounds, and tapes through the mail resulted in Fragment 56.
Also in 2001, Randy Greif released the second Shadowbug 4 CD, titled We Are Beginning Our Descent, and continued his themes of depression and angst by way of dark ambience, slow beats, glitchy electronics and cut-up voices.
During the years between 2001 and 2006, Greif wrote and directed the feature film The Three Trials with the following description: "Catherine, a nun with a unique form of narcolepsy, attempts to lose herself in the worlds of religion, adolescent fantasy, and finally masochistic devotion to a man.
The viewer is left to interpret what is real, what is dream, and what is false narrative in this feverish, pitch-black comedy with a smorgasbord of sexual fetishes."
Also in 2007 a CD in collaboration with Anna Homler, Brad Cooper and Adam Smith (under the name of Drift) was released on his own Swinging Axe label entitled Bypass Through The Sky.