175. Coolness
Listen to Ellie and David talk about coolness in episode 175 of overthink!
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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
Highlight: Ironic detachment
Ironic detachment, along with narcissism and hedonism, is one of Pountain and Robins’s criteria of coolness.
It involves a wholesale rejection of sincerity and an unwillingness to express interiority. The cool person doesn’t say what they really care about, and they don’t want to seem invested in anything.
Pountain and Robins point out that coolness spread in the post-war period. They argue that the horrors of the war led to a widespread disillusionment, where people found it hard to latch onto values. They thus turned inward, focusing on private experience and leading to ironic detachment from the world.
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Thank you for listening to another episode of Overthink! Leave your thoughts in the comments!





Loved this episode, but the “youth defines cool” framing felt off to me. Maybe I missed the plot, but I think we have to separate trendiness from coolness. While I agree that youth culture drives contemporary aesthetics, slang, fashion, and what feels current, I don’t think young people unilaterally decide what counts as cool across every context and community.
Instead, I think every culture develops its own standards for taste, status, and admiration. Outsiders usually are not in a position to define what is or isn’t cool inside groups they do not meaningfully participate in. Cool is a form of social power; thus, it is contextual and peer defined. Basically, you can’t hate from outside the club.
For example, I work in law, which mainstream culture considers pretty uncool compared to fields like sports, arts, fashion, etc. But within law firm culture, there are absolutely people who are cooler than others. There’s an attorney at my firm who somehow makes wearing a women’s business suit (objectively the least inherently cool category of clothing imaginable) look effortlessly cool because she has exceptional style and presence. A 20 year old might not see her that way, but among lawyers in our world (i.e. the target audience), she’s undeniably cool and stylish!
Same with other niche communities. I went to a Star Trek convention with my sister a few years ago, and there were definitely people there who my sister perceived as cool within that world, though I personally never would have picked them out. Andrew Tate is cool to 13 year old boys because he is the distilled fantasy of masculinity for under-parented boys. But to most people his own age, he comes across as deeply cringey and performative. It’s the college freshman who may be a huge dork on campus but is the coolest person imaginable to their younger sibling’s friends. Coolness changes depending on who is bestowing the title and what that group values.
In defense of my people, I don’t think middle aged women have a coolness deficit, but instead are invisible to the metrics media uses to measure cultural relevance. Fwiw, as an early 40 something, I think Ellie and David are extremely cool!! Hosting an interesting podcast where you get to flex your expertise and have thoughtful conversations is literally peak cool for us overthinky millennials! 🪦