Among Wilson's 35 books, and many other works, perhaps his best-known volumes remain the cult classic series The Illuminatus! Trilogy (1975), co-authored with Robert Shea. Advertised as "a fairy tale for paranoids," the three books--The Eye in the Pyramid, The Golden Apple, and Leviathan, soon offered as a single volume—philosophically and humorously examined, among many other themes, occult and magical symbolism and history, the counterculture of the 1960s, secret societies, data concerning author H.P. Lovecraft and author and occultist Aleister Crowley, and American paranoia about conspiracies and conspiracy theories.
Wilson and Shea derived much of the odder material from letters sent to Playboy magazine while they worked as the editors of the Playboy Forum. The books mixed true information with imaginative fiction to engage the reader in what Wilson called "guerrilla ontology" which he apparently referred to as "Operation Mindfuck" in Illuminatus! The trilogy also outlined a set of libertarian and anarchist axioms known as Celine's Laws (named after Hagbard Celine, a character in Illuminatus!), concepts Wilson revisited several times in other writings.
Among the many subplots of Illuminatus! one addresses biological warfare and the overriding of the United States Bill of Rights, another gives a detailed account of the John F. Kennedy assassination, in which no fewer than five snipers, all working for different causes, prepared to shoot Kennedy in Dallas, Texas, and the book's climax occurs at a rock concert where the audience collectively face the danger of becoming a mass human sacrifice.
Illuminatus! popularized Discordianism and the use of the term "fnord". It incorporates experimental prose styles influenced by writers such as William S. Burroughs, James Joyce, and Ezra Pound. Although Shea and Wilson never partnered on such a scale again, Wilson continued to expand upon the themes of the Illuminatus! books throughout his writing career. Most of his later fiction contains cross-over characters from "The Sex Magicians" (Wilson's first novel, written before the release of Illuminatus!, which includes many of his same characters) and The Illuminatus! Trilogy.
Illuminatus! won the Prometheus Hall of Fame award for science fiction in 1986, has many international editions, and found adaptation for the stage when Ken Campbell produced it as a ten-hour epic drama. It also appeared as a Steve Jackson role-playing card game called Illuminati and a trading-card game called Illuminati: New World Order. Eye N Apple Productions and Rip Off Press produced a comic book version of the trilogy.
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