AbstractThe term “cool” likely originated in American jazz in the 1940s and was a superlative that indicated significant achievement within an aesthetic of restraint. Over the ensuing decades, the word evolved to mean a rebellious vision that breaches tradition and repudiates past versions of cool. Even though its linguistic roots are West African, the term accrued distinctly American connotations in racist, sexist, and homophobic contexts. The shimmering, mysterious indefinability of coolness—its you‐know‐it‐when‐you‐see‐it quality—helped conceal its phobic qualities. The author examines the homophobic context through the lens of an icon of cool, James Dean, who became for gay men an object both of identification and erotic desire. The essay considers whether the restraint of coolness is only masquerade, a product of disavowed bodily anxiety, or if it also represents integration and meaningful transformation. A clinical vignette and scenes from the film Rebel Without a Cause are used to exemplify these dilemmas from a psychoanalytic point of view.