The particular evolution of Zen paintings during the Edo period, including the artwork of Hakuin Ekaku (1685-1768) and Sengai Gibon (1750-1837) is usually referred to as Zenga (禅画; lit. Zen paintings). These paintings are part of a long tradition of Zen ink painting that began following the importation of Zen Buddhism from China at the beginning of the Kamakura period (1185-1333). The central aim of this paper is an examination of the attitude of Hakuin and Sengai toward this tradition through two main inquiries: In what way do Hakuin and Sengai encounter with the past? What are the manifestations of this attitude in their artwork? The answer to these questions can be found, as I will claim, in two voices in Zen literature concerning tradition and doctrines, which seemingly contradict each other. On the one hand, prominence is given to regulation, hierarchy, authority, and tradition, but on the other hand, there is appreciation and respect for rule breakers and free-spirited individuals whose awakening enabled them to break with tradition. This notion will be examined through an analysis of both texts and images of some of Hakuin and Sengai’s artwork.