This article attempts to shed light on the cultural understanding of laughter in the East and in the West. More specifically, it introduces the sages who take laughter as their signature both in China and in Europe and identifies the understanding of laughter as a qualification of wisdom in different cultures. In China, the earliest model is the Daoist sage, whilst in the West it is the 5th century BCE atomist philosopher, Democritus, later nicknamed the Laughing Philosopher. The Chinese ideal of the laughing sage had a more widespread influence than the Western ideal, through its endorsement by Chinese Buddhism, and the latter's influence both on Tibetan Buddhism and Japanese Zen Buddhism, combined with the Western interest in Daoism, Buddhism and Zen. In contradistinction, the legend of the laughing philosopher would remain mostly cooped in Europe and travelled little. However, as with the laughing Buddhas and the Zen laughing monks, who bring Daoist influence to religion and to art, Democritus's influence within Europe will be palatable not only in philosophy, but also in religion, literature, and iconography. In what follows, I elaborate first on the laughing philosopher, epitomized in the West by the legend of the sage Democritus and on additional Western sources of laughter. I then turn to Chinese philosophy, and explain how the laughing sages of Daoism influenced Chinese or Ch'an Buddhism, which gave rise to the significant role of laughter in Zen Buddhism. I conclude with some cultural differences, which are transcended by the role of laughter in securing and restoring health in both the East and the West and especially by the commonalities of the human condition.