This article examines how Chinese and Japanese Zen painters portrayed Bodhidharma, the semi-legendary Indian monk revered as the first patriarch of Chan (Zen) Buddhism. The author first reviews the sources and legends surrounding him, from Tanlin’s early account to the Zutangji (952): the audience with Emperor Wu of Liang, in which Bodhidharma declares that the highest truth is “open and wide, not holy”; his nine years of meditation near the Shaolin monastery; and the transmission to his successor Huike. These stories, the author argues, already contain the essence of Zen, namely that ultimate truth cannot be put into words; painters accordingly depicted the founder as an ordinary, sometimes grotesque figure stripped of all transfiguration. The article then compares two versions of the popular motif of Bodhidharma crossing the Yangzi on a reed: a thirteenth-century scroll by Li Yaofu with an inscription by Yishan Yining, rendered in pale baimiao outline and diluted “shadow painting”, and a seventeenth-century version painted in Japan by Xueji Dingran of the Huangbo (Ōbaku) lineage. Their close kinship illustrates the East Asian principle of learning from earlier masters, while the crossing becomes an allegory of the courage of those who carried Zen eastward.