“Blackness is expansive,” Damon Young said recently in a video discussing his new memoir in essays, “What Doesn’t Kill You Makes You Blacker.” It would be easy to interpret the author’s statement as the insistence that “black people aren’t all the same,” especially in light of a comment he makes later in the video: “White America tends to think of black America on a more narrow spectrum.” In fact, his book boldly and hilariously pushes back against what Young describes as a “neurosis”: the anxiety that arises from a prying white gaze that demands to have the intimate and complex details of black life rendered completely accessible. Young, who co-founded the cultural criticism website Very­SmartBrothas.com, is mostly unconcerned with what white America thinks of black people. Instead, with candor, self-awareness and considerable humor, he turns an unflinching eye on both himself and an American society constructed and sustained by racism.

In “Street Cred,” the author explores his inability to rack up cool points at his high school despite having all the necessary elements, including star basketball player status, frequent appearances in local newspapers and interest from college teams. He also possesses actual “hood bona fides” on account of where he grew up, unlike his far more popular nemesis James Adams, who Young characterizes as being “about as hood as Gwyneth Paltrow.” The essay details how the combination of James’s charisma, bravado and performance of hood coolness obscure the fact that he is not nearly as successful an athlete or student as our narrator, yet still has enough social capital to attempt to embarrass him publicly.

Like most of the essays in Young’s book, “Street Cred” is about much more than the overt theme it presents. Beyond the chronicling of teenage angst and desire for acceptance from one’s peers, Young is also talking about segregation in housing and school districts, and about the lengths black parents go to in order to give their children access to a decent education. It’s also about the delusions we feed ourselves and those we love, and about how our self-doubt can manifest in diminishing ourselves and projecting onto the people around us. In highlighting the anxieties he shares with his classmates about class and what it means to be black at a majority white suburban high school, in a segregated city, in a segregated country built on stolen land, Young presents a critique of what qualifies as “authentic” blackness, and the performances of gender and cultural signaling that it requires. This insight allows him to empathize with James, while also admitting that he is still petty enough to wish the most benign of misfortunes on him, including dropping his spaghetti on a floor covered in cat hair.

“Bomb-Ass Poetry” is another chapter that stands out, starting with an opening line — “Darius Lovehall was trash” — that may be fighting words for fans of the 1997 black romance “Love Jones.” Young’s analysis of Larenz Tate’s character in the film and his pursuit of Nina Mosley, played by Nia Long, does more than poke fun at the mud-cloth-clad, artsy, bougie black crowd depicted in the film; he uses Darius as an entry point to narrate his own journey with poetry as a college student, and his unrelenting and borderline creepy courtship of his friend and unrequited crush, Tracey. With his usual unrestricted honesty, the author even includes some of the poems he shared with Tracey, containing lyrical gems such as “made my blues MO’ BETTER” and an inevitable reference to Cleopatra. Young discusses the extent to which his interest in Tracey became less about her as a person than it was about proving something about his masculinity to the people around him.

Young’s reflections on hyper-masculinity and on gender in general are not without their fraught moments. In “How to Make the Internet Hate You in 15 Simple Steps” the author revisits how he came by this knowledge when he responded to a sexual assault survivor’s article on victim-blaming with his own flippant and ill-advised article. While he rightfully points out the danger of “decent” black men, who consider themselves allies to black women and queer black people, believing their decency absolves them of committing harm, his account of the growth he has undergone and his understanding of gendered power dynamics still has an uncomfortable undertone. The essay runs the risk of asserting the narrative that a cis-hetero black man’s self-improvement must necessarily come at the expense of the women and queer people around them. At the very least, the author recognizes this sense of entitlement, and the essay is an exercise in grappling with the misogyny he continues to unlearn.

What remains most memorable about Young’s work is his ability to access and inhabit his consciousness at different stages of his life, without projecting his present outlook on the younger iterations of himself. Young succeeds at creating a clear distinction between the narrative voice that has already lived through these various joys and trials and his less experienced voice navigating the usual awkwardness of youth alongside the realities of growing up as a black boy in Pittsburgh in the 1980s and ’90s. Above all, his writing is hilarious, as in laughing so hard that you end up in tears or, sometimes, laughing hard enough to stop the tears from flowing.

Zoë Gadegbeku is a Ghanaian writer living in Boston.

What Doesn't Kill You Makes You Blacker

By Damon Young

Ecco. 320 pp. $27.99