In Sung and Yuan dynasties, paintings with Han Shan were popular. In the “Painting of Four Sleepers” with Han Shan, Shih Te, Feng Kan and tiger sleeping together, character modeling and image characteristics are metaphorical with Zen. Concept of “four sleepers” should be the extension of construction of “three hermits” of Tiantai. Participation of tiger is originated from the legend in which Feng Kan arrived at Kuo Ching Temple by riding a tiger and stayed in Zen room with the tiger. In Buddhism, sleeping means “Nivarana” which lays over wisdom. If “sleeping tiger” symbolizes taming of worry, how do four sleepers show “Styana-middha”? Based on “Painting of Four Sleepers” and verses in Sung and Yuan Dynasties, this study discusses different Zen masters’ composition and image in creation of “four sleepers” and implication of change in Zen related to Sung Tsan. Moreover, it examines compatibility between painting and verses, and explores metaphorical meaning of “four sleepers” in Zen and multiple interpretations of different Zen masters verses.