Some noodling on piano and bass, and then the former plays a D and an A. Bill Evans on the piano and Paul Chambers on the bass, trading back and forth until the trumpet of Miles Davis erupts about seven measure into “So What,” the first track off Kind of Blue, perhaps the most seminal album of cool jazz recorded during the 1950s. There are no lyrics to “So What,” but that staccato rise of D to A throughout the track easily sounds to the ear like the title of the song could be overlaid onto it, like the ever unflappable and almost painfully cool Davis is shrugging off any accolades you could give his effortless genius. Miles Davis already knows that he’s a genius. The album, Birth of the Cool, released two years earlier, may have been more literal in its title, and it is indeed cool, but something about the melodic theme of “So What” expresses the ineffability of that strange quality of cool that is impossible to surpass.
A musician of many lives and styles, it’s the Davis around the time of the Kind of Blue that most exemplifies coolness, the sleight man with a troubled gaze and a prickly personality in his Brooks Brothers khakis and his white button-down with the sleeves rolled up to the elbow, languidly holding his trumpet while looking out over his black sunglasses and almost daring the listener to think he can even approach his level. “For me,” he writes in Miles: The Autobiography, “music and life are all about style,” and that style was cool. Davis didn’t invent coolness, but he perfected it.
Cool, and its attendant category of hip, are difficult to theorize, because their slipperiness and ambiguity are part of what’s intrinsic to them. Neither is synonymous with popularity, far from it actually, though it’s often taken to mean that in general parlance. Nor does it mean great in that canonical, ossified, Great Man sort of way, though talent is part of it, as long as that talent appears effortless and unagitated. Coolness isn’t dissimilar to what the Renaissance Italians called sprezzatura, a kind of graceful nonchalance, which is closer to the twentieth century American meaning of the word that has been used in English since the time of Shakespeare, but originally tended to mean remaining calm when other people didn’t.
The nearest analogue to coolness as expressed in the music of someone like Davis or saxophonist John Coltrane, not to mention the bop prosody of poet and novelist Jack Kerouac, the ironic pose of standup comedian Lenny Bruce, the icy gaze of actor James Dean, stuttering and bored artist Andy Warhol next to his painting Campbell’s Soup Cans, or even the trickster antics of Bugs Bunny, is the Yoruba and Igbo concept of Itutu. Art historian Robert Farris Thompson writes in the journal, African Arts, that Itutu deals in individual control and composure, but also that such “coolness has to do with transcendental balance,” that coolness is a spiritual quality as much as it is a matter of fashion, expressing membership amongst those whom Allen Ginsberg called “Angel-headed hipsters” in his poem Howl. In this sense, coolness is both a mode and an affect, an approach and a personality, but most of all cool is an aesthetic – and an orientation, a perspective, a way of being.
Hip, which has a bit more of an association around exclusionary fashion, is nonetheless related to coolness. There is a sense of knowingness about hip, which is indeed the etymological origin of the word itself, from the Wolof phrase “hepicat” which meant “to open one’s eyes,” and where both “hip” and “hep-cat” derived. The quality of hip is about fluidity and indeterminacy; it’s about appropriation and experimentation; it’s about removing the screws from the doors and the doors from their jambs. And, inculcated in the forge of America where Africa and Europe met, under the most horrific of circumstances, hip and cool became the dominant aesthetics of American culture. “For better and worse,” writes journalist John Leland in Hip: The History, “hip represents a dream of America. At its best, it imagines the racial fluidity of pop culture as the real America, the one we are yearning to become… Its gaze is the knowing, raised eyebrow… skeptical but not unkind.” Both hip and cool are endlessly appropriated; Madison Avenue making its jaunt Downtown to MacDougal Street since time immemorial, but by its very nature, both are countercultural, in opposition to the dictates of normie and square society. Norman Mailer in his 1957 Advertisements for Myself, surveying the cool jazz of a Davis or the antiestablishment pose of the Beats, explained the dichotomy of “Hip-Square” whereby the latter may be practical, classic, orderly, pious, and determined, but the latter is wild, romantic, spontaneous, perverse, and free. The square lives in society while the hipster lives for themselves; the normie exists for noon but the hep-cat is a creature of midnight. Most of all, hipness is in some sense concurrent with Blackness, while to be mainstream is to be as white and square as a cracker.
Not that there weren’t cool white musicians – ask Chet Baker, listen to Lou Reed. But both coolness and hipness – Itutu and hepicat – left their West African origins only to be molded and melded by the traumas of America, were both become a perspective but also a survival strategy. The result is that coolness became the dominant American cultural aesthetic, with a lineage that traces to before and after Kind of Blue. To be cool is to be Walt Whitman leaning, and loafing, and inviting his soul; of Mark Twain throwing his lot in with Huck and Jim instead of Tom; of Artie Shaw swinging on the clarinet (but definitely not Glenn Miller); of Jackson Pollock dribbling paint on a canvas and Frank O’Hara doing rounds at the Museum of Modern Art; implacably smooth Malcolm X in his black suit and wireless glasses; Bob Dylan’s amphetamine twitching during a British news conference or the Velvet Underground performing at the Plastic Fantastic Inevitable. Cool isn’t about people liking you, but rather being comfortable in your own skin, and brandishing that comfort as a type of weapon against that which conspires to constrain you. Leland writes that “If hip is a form of rebellion… it should want something. Its desires are America’s other appetites, not for wealth but for autonomy. It is a common folk’s grab at rich folk’s freedom – the purest form of which is from the demands of money. It is an equalizer,” for as the critic explains, “Anyone can be hip, even if everyone can’t.”
Reprinted with permission from American Elegy: 250 Years of the Dis-United States of America by Ed Simon, published in © 2026 by Ig Publishing. All rights reserved.
