playboy meaning , definition , what is playboy : a rich man who does not work and who spe...: Learn more. Playboy definition: a man who pursues a life of pleasure without responsibility or attachments, especially one who is of comfortable means.. See examples of PLAYBOY used in a sentence. The word "playboy" is a compound of "play" and "boy," suggesting a youthful or carefree spirit focused on leisure and pleasure rather than serious responsibilities. The earliest recorded use of the term dates back to the 19th century, but it gained prominence in the mid-20th century. A playboy lifestyle is the lifestyle of a wealthy man with ample time for leisure, who enjoys the luxuries and physical pleasures of the world, especially including the sexual company of women.