At the heart of Cattelan's practice is an exploration of contradiction. His works often appear playful or deliberately absurd, yet beneath their humour lies a sharp examination of contemporary culture and human behaviour. Cattelan encourages viewers to question their assumptions about authority, success, religion, and social convention. Works such as La Nona Ora, depicting Pope John Paul II struck by a meteorite, and Him, a sculpture of Adolf Hitler kneeling in prayer, demonstrate his ability to confront politically and culturally charged subjects through deceptively simple and visually striking compositions. His practice frequently occupies the uncertain space between comedy and discomfort, forcing audiences to consider why certain images provoke laughter, outrage, sympathy, or unease.

Throughout his career, Cattelan has consistently challenged the conventions of artistic production and presentation. Rather than adhering to a single medium or traditional artistic methodology, he has embraced sculpture, installation, taxidermy, found objects, and conceptual interventions, often using theatrical presentation to amplify the psychological impact of his work.

His iconic Comedian, consisting of a banana duct-taped to a wall, became one of the most widely discussed works of contemporary art in recent years, questioning ideas of authorship, originality, value, and the relationship between an artwork and its audience.

Cattelan's work has been exhibited at many of the world's leading museums, galleries, and international exhibitions, including the Solomon R. Guggenheim Museum, Tate Modern, Centre Pompidou, Museum of Contemporary Art Chicago, and the Venice Biennale. His retrospective at the Guggenheim Museum in New York, All, presented his entire body of work suspended within the museum's iconic rotunda, reinforcing his reputation for transforming the conventional relationship between artwork, institution, and viewer. His works are held in significant public and private collections internationally, while his exhibitions and projects continue to generate substantial critical and public attention.

Cattelan occupies a highly distinctive position within the international contemporary art market. His exceptional recognisability, strong institutional history, and ability to generate sustained cultural discussion have contributed to significant collector demand. Cattelan's combination of conceptual importance, rarity, cultural visibility, and market recognition makes him one of the most compelling contemporary artists for collectors seeking works that combine intellectual significance with strong visual and cultural impact.