Being witty and being culturally appreciated are two independent things in visual communication design. More often than not, on one hand, the Japanese sense of ‘playfulness’ is manifested in enigmatic images, which express intriguing aspects of Japanese psyche. On the other hand, the Western sense of humor is often light hearted, as its major aim is to raise a smile instead of ambiguity. This ethnographic study examines the essence, categories, and sentiment of playfulness in Japanese context. It also explores in detail the situations in which playfulness is used and, where permitted, how Japanese artists and designers come up with playful ideas and encode meaning in their works. The conclusion focuses on how the Japanese sense of playfulness has long been used to establish cultural influence, social voice, and individual distinction.