This is the third essay in a series on digital identity, culture, and social life. The first part takes up an essay by art critic Sean Tatol. The second part examines a play by playwright Matt Gasda. The third part, the heart of the essay, develops an account of digital experience and identity, which culminates in the ‘death of the cool’. Thank you sincerely for reading.IIn his September 2024 review essay “Manhattan Syndrome: A Survey of New York Trends”, the art critic Sean Tatol identifies a growing tendency toward what he calls “art-cool reflexivity”, in which “the coolness of the New York artist existing in New York” constitutes the form and content of the artwork. One characteristic example he details is the Win McCarthy exhibition “Kingdom Come” at Francis Irv. Composed of distorted iPhone panoramas of New York scenes, stacks of bricks and plastic take-out containers, and a cropped photo of a wheatpasted lingerie ad, McCarthy’s show, Tatol writes, is a “stylized evocation of walking around downtown”, reminiscent of “hanging out on a Chinatown rooftop”, “clearly evocative of the cool, aloof NYC feeling that it’s going for”. While such hyper-self-consciousness might inspire eye-rolling, Tatol identifies this reflexive tendency not to condemn it, but rather to suggest that it is a distinctive feature of the “emergent impasse” in artmaking which contemporary artists are struggling to break through.For Tatol, this impasse – the widely acknowledged “aimless and uninspired state” of the arts, the art world’s inability to produce things of “lasting interest or value” – is inextricably linked to a “crisis of cool”. Certainly it can be traced to some degree to the shortcomings of the patronage class, interested on the one hand in the rising asset values of art, and on the other hand in art as a moral and political vehicle. But there is a more fundamental, existential problem, he argues, within the supposedly highbrow milieu of downtown artists itself. The origin of many