This chapter explores the ontological implications of laughter by confronting European thought with East-Asian Zen thought. Using the central figure of the Monkey King from Journey to the West, it explores laughter in the context of Buddhist emptiness (śūnyatā). In what way is emptiness a “barrel of monkeys”? After some introductory reflections on the central problematic, I turn to European thinkers and writers like Milan Kundera, Friedrich Nietzsche, and Georges Bataille, and then turn to the Chinese and Japanese Zen traditions as well as to the Kyoto School luminary Keiji Nishitani. The Zen problematic of emptiness reveals the ontological dimensions and conundrums of laughter. And given that laughter itself is empty, it becomes a comic and strange problem itself.