Cattelan started his career in Forlì (Italy) making wooden furniture in the 1980s where he came to know some designers like Ettore Sottsass.

He made a catalogue of his work which he sent to galleries. This promotion gave him an opening in design and contemporary art. He created a sculpture of an ostrich with its head buried in the ground, wore a costume of a figurine with a giant head of Picasso, and affixed a Milanese gallerist to a wall with tape. During this period, he also created the Oblomov Foundation.