Among the most memorable outings I’ve spent at a comedy club was an evening that was predicated only tangentially on comedians. There were funny people on hand at the Comedy Cellar that night, including notables like Judy Gold, Shane Gillis, and Andrew Schulz, but the event was centered around people who earn their money by other means: a journalist with a degree in philosophy and two economists, each with a knack for getting into hot water. Among the latter was the Merton P. Stoltz professor of the social sciences at Brown University, Glenn Loury.

Anyone who has had even half-an-eye trained on the news over the last decade or so knows that stand-up comedy has been at the center of the culture wars, particularly as it applies to free speech. Yet even the comedians that night — forget the audience — were left agog at a series of “unspeakable truths” posed by Mr. Loury. These included observations about Black Lives Matter, Jews, Donald Trump, transgender rights, standardized tests, and mental health. You can hear these comments posted on YouTube. It makes for a bracing watch.

Mr. Loury’s autobiography, “Late Admissions: Confessions of a Black Conservative,” isn’t as bracing, nor does it catch the vigor of his podcast, “The Glenn Show.” Chalk up the distinction to the degree of measure required for the literary casting of a life compared to the moving-on-your-feet nature of recorded conversation. His biweekly conversations with a Columbia University linguist, New York Times columnist, and “cranky liberal,” John McWhorter, are particularly spirited.

Still, “Late Admissions” sets down a gauntlet right out of the gate: “We are playing a game, you and I, reader and author.” Whereupon, Mr. Loury muses on the nature of autobiography, the subterfuges that are sometimes put into effect and, ultimately, the credibility of the person telling the story. He’s peculiarly cognizant of those who might cast a jaundiced eye on how one man’s moral compass may — or may not — correspond to the same man’s behavior and accomplishments.

“I know you are going to be on the lookout for anything that discredits my story,” he writes, “I will dispense [discrediting information] freely, openly and undisguised.” Mr. Loury is out to establish a no-holds-barred authenticity: “Late Admissions” is a serpentine tale of hardscrabble triumphs and slap-upside-the-head transgressions. 

Born in the Manor Park section of Chicago, Mr. Loury grew up in an environment that was, if not strictly Rockwellian, then suitably loving and respectably working-class. The regal and righteous Auntie Eloise is one gauge of childhood; Uncle Alfred and his tomcatting ways, another. Their poles of behavior set precedents that Mr. Loury would shuttle between through the better part of his travels.

Young Glenn proved adept at mathematics. After initially stumbling at the Illinois Institute of Technology — Mr. Loury, to use a favored bit of terminology, “choked” — he went on to a remarkable array of accomplishments. After receiving a degree from Northwestern University, Mr. Loury earned his Ph.D. in economics at MIT and then became a tenured professor at Harvard University, the first Black man to do so — at the ripe young age of 33. 

Then, Mr. Loury blew it. At several points during “Late Admissions,” he puts the brakes on the narrative in order to distinguish between the “cover story” and the “real story.” Even as he was gaining notice for his scholarly endeavors and intellectual iconoclasm, Mr. Lowery was occupying his off-hours by stepping out behind the back of his wife, ever patient and forgiving Linda. His adulteries ranged from the fleeting to the long term, with Mr. Loury, at one time or another, footing the bill for secret apartments, secret vacations, and, not least, a secret drug addiction.

Misprising his reputation as a public intellectual, he took on the role of, pace Tom Wolfe, Master of the Universe. Mr. Lowery’s hubris was flagrant but it was not impenetrable. When the good professor was being vetted for a potential position with the Reagan administration, information about his extramarital dalliances, as well as a son he had long abandoned, came to light. Mr. Loury pulled his name out from consideration. Actions have consequences, even for a Player.

Mr. Loury’s life has been a constant push-and-pull between the foundational aspects of African-American life and cultural pursuits that are sometimes seen as incommensurate with them. Toward the latter part of the book, Mr. Loury relates how his Uncle Alfred responded to a lecture he had given at the University of Chicago: “I don’t see anything of us in what you do. Don’t you realize that we are a people apart here in America, that we’re in a fight to the death. And now, professor, it seems like you joined the other side.”

Uncle Alfred’s esteemed nephew was as heartbroken as he was angry about the assumptions made of who he is and what he should be: “True authenticity must run deeper than some outdated notion of white oppression.” He goes on to James Joyce citing his own beliefs about liberty and identity, means and ends. Yet his dilemma seems equally of a piece with Feodor Dostoevsky and the Underground Man, of individuality “carried to an extreme … what you have not dared to carry even halfway.” “Late Admissions” is a tough and fascinating read.