What is the value of intellectual playfulness? Traditional characterizations of the ideal thinker often leave out playfulness; the ideal inquirer is supposed to be sober, careful, and conscientiousness. But elsewhere we find another ideal: the laughing sage, the playful thinker. These are models of intellectual playfulness. Intellectual playfulness, I suggest, is the disposition to try out alternate belief systems for fun – to try on radically different perspectives for the sheer pleasure of it. But what would the cog-nitive value be of such playfulness? I suggest that intellectual playfulness function as, at the very least, a kind of intellectual insurance policy against epistemic traps. An epistemic trap is a belief system that re-directs good-faith inquiry to bad results. Am epistemic trap manipulates background beliefs to fend off contrary evidence. For example, a conspiracy theory might include a set of beliefs about how the mainstream media has been taken over by some vicious cabal. Normal epistemic attempts will be captured by a well-wrought epistemic trap, because normal attempts at inquiry are guided by these background beliefs -- which set what counts as a plausible path to explore, and what is implausible or beyond the pale. And a clever epistemic trap will manipulate those background beliefs for ill effect. Intellectual playfulness, on the other hand, isn’t motivated by an epistemic interest in the truth, but in the sheer pleasure of intellectual exploration. Since intellectual playfulness isn’t oriented towards the truth, it won’t be constrained by an agent’s background beliefs – it won’t, for example, prefer to investigate apparently more plausible pathways. Intellectual playfulness offers an opportunity to escape from epistemic traps. But intellectual playfulness has its own limitations. It will only drive us to explore belief systems when that exploration is fun. What we need is an array of differently-motivated exploratory tendencies – empathy, curiosity, playfulness – each of which will each cover for the others’ limitations.