The riddles of the Sphinx and of Samson are examples of how they tell a fascinating side-story about human destiny. The inability to solve a riddle was believed to bring about dire consequences to heroic figures. Riddles emerge as part of oral traditions, likely recited by elders or oracles in early cultural settings, and later by designated orators. The Riddle of the Sphinx is one of the earliest written riddles, going back to around 2500 bce by most estimates. The riddle reveals, in its miniature way, that understanding occurs by connecting images metaphorically. The language of riddles is akin to the language of jokes. Like the latter, riddles can be composed on purpose to make fun of something or, simply, to provide a type of comic relief. Riddles are evidence of the human brain’s ability to visualize the universe as a coherent organism. They emerge as oral tradition and as intrinsic to the expression of wisdom.