Andrew Dice Clay was born Andrew Clay Silverstein in Brooklyn, New York. In the early stages of his career, using the name Andrew Clay, he was an actor and appeared in '80s low-budget porn films, along with sitcom appearances on M*A*S*H and Diff'rent Strokes and a regular role on Crime Story. He eventually gave up acting and turned his hand to standup comedy, inventing a persona known as The Dice Man. Named after a Luke Rhinehart novel, the persona was that of a highly racist, homophobic woman-hating street wise Brooklyn tough guy.

Unlike many other comedians who turned their comedy into a tool of political or social commentary, including contempories like Bill Hicks and Sam Kinison as well as influences such as George Carlin and Lenny Bruce, Clay's desire was to be as shocking as humanly possible. His material consisted of highly sexist routines, portraying women as sex objects and nothing more, and would regularly portray minorities, both racial and sexual, in a derisory fashion.

Dice would often insult members of his audience while they were actually there, and made many so uncomfortable that they actually left his shows. At this time, his most popular routine involved the subversion of traditional Nursery Rhymes, including "Jack and Jill went up the hill" and "Little Miss Muffet", turning them from child friendly rhymes into sordid sexual encounters. It was these rhymes that subsequently became both Dice's breakthrough into the mainstream as well as the routine that he most despised.