Burroughs and the monstrous have always gone together, and this chapter examines how not only his work but Burroughs himself was from the start defined in terms of monstrosity. It traces the origins of the association back to his early critical reception and even earlier fictionalization as a profoundly sinister persona in the novels of Jack Kerouac. The specific grounds for identifying Burroughs or his work as monstrous have changed over time, often focusing on ambiguously misogynistic, racist, homophobic, or anti-Semitic content, and on his identity as a homosexual and drug addict. His accidental shooting of his second wife, Joan Volmer, has cast the darkest shadow, but, this chapter argues, it has obscured the actual significance of monstrosity in Burroughs’ work. This, as critics such as Wermer-Colan and Stevenson have argued, lies in how he embraced complicity rather than hypocritically denied it, resulting in strategies that weaponize monstrosity as a mirror for the dark forces at work in the world.