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Coolness

May 26, 2026 · 55 min

Show notes

Play it cool and play this episode. In episode 175 of Overthink, Ellie and David talk about what it means to be cool. From swag gap relationships to Mark Zuckerberg and the manosphere’s failed attempts at being cool, your hosts examine coolness’s ties to youth and subversion and its opposition to displays of wealth. They trace how coolness emerged from Black American culture in the 1930s, before being associated with Beat Poets and punk musicians. They consider precursors to cool, like the Italian term sprezzatura, and question the ontology and the morality of coolness. Is coolness an attitude or a state? Is it inherently narcissistic? Can you ever successfully “try” to be cool? In the Substack bonus segment, Ellie and David discuss coolness through an ethical perspective.

Works Discussed:

Joel Dinerstein, “Jazz Cool”

Ted Gioia, The History of Jazz

bell hooks, We Real Cool: Black Men and Masculinity

Dick Pountain and David Robins, Cool Rules: Anatomy of an Attitude


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