A self-taught artist, Cattelan began his career designing furniture but turned to sculpture and conceptual art in the early 1990s and quickly garnered a reputation for a sense of humour and a penchant for blurring the distinction between art and reality. He described himself as a “lazy” artist and told The Guardian newspaper that “I don't do anything.” Some of his actions backed up the latter claim. In 1992, for example, he assembled a group of donors to award him a $10,000 grant that stipulated that he not exhibit any artwork for one year. At the 1993 Venice Biennale, he made a statement (and a profit) by subletting his exhibit space to a perfume company. At an exhibition in Turin, Italy, he knotted bedsheets together and hung them out a window, giving the impression that he had left the building.

In truth, however, Cattelan did plenty of creating. In 1999 he exhibited La nona ora, which depicted Pope John Paul II having just been struck by a meteorite. That same year at a London gallery, he displayed a miniature replica of the Vietnam Veterans Memorial, located in Washington, D.C., that had engraved on it the score of every football (soccer) match lost by the English national team. His commemoration of the September 11 attacks on the World Trade Center, Frankie and Jamie (2002), showed two wax figures of New York police officers standing upside down. Despite so much satiric critique of the art world and society in general, Cattelan deftly managed—for the most part—to enthrall rather than enrage his audience and his peers.