Laocoön and his Sons

Titian's parody of the Laocoön as a group of apes

Laocoön as an ideal of art

Pliny's description of Laocoön as "a work to be preferred to all that the arts of painting and sculpture have produced"[3] has led to a tradition which debates this claim that the sculpture is the greatest of all artworks. Johann Joachim Winkelmann wrote about the paradox of admiring beauty while seeing a scene of death and failure. The most influential contribution to the debate in Gotthold Ephraim Lessing's essay Laocoon: An Essay on the Limits of Painting and Poetry, which examines the differences between visual and literary art by comparing the sculpture with Virgil's verse. He argues that the artists could not realistically depict the physical suffering of the victims, as this would be too painful. Instead, they had to express suffering while retaining beauty.

The most unusual intervention in the debate is William Blake's annotated print Laocoön, which surrounds the image with graffiti-like commentary in several languages, written in multiple directions. Blake presents the sculpture as a mediocre copy of a lost Israelite original, describing it as "Jehovah & his two Sons Satan & Adam as they were copied from the Cherubim Of Solomons Temple by three Rhodians & applied to Natural Fact or History of Ilium".[4] This reflects Blake's theory that the imitation of ancient Greek and Roman art was destructive to the creative imagination, and that Classical sculpture represented a banal naturalism in contrast to Judeo-Christian spiritual art.

In 1940 Clement Greenberg wrote an essay entitled Towards a Newer Laocoön in which he argued that abstract art now provided an ideal for artists to measure their work against, and this title was copied by a 2007 exhibition at the Henry Moore Institute.