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This chapter compares two sixteenth-century treatises on painting, Da pintura antiga / Do tirar polo natural (1548-1549) by Francisco de Holanda and Comentarios de la pintura y pintores antiguos (c. 1560) by Felipe de Guevara. Although both treatises represented contemporary Iberian ideas on painting, the two authors’ ideas were shaped differently by the particular artistic discourse and cultural context of Italy and the Netherlands respectively. De Holanda’s and De Guevara’s considerations about the defining factors of the art of painting were furthermore determined by their diverging backgrounds as court painter and collector.