Ideally, a boy’s biggest concerns on his first day of fourth grade would be whether his lunchbox is cool enough and which teachers will assign the most homework. Things were more complex for David Matthews, who in 1977 moved from suburban DC to Baltimore, a rigidly segregated city in which

David, half black and half white, found no natural crowd. Twenty minutes after being dropped off at school, he was besieged by a pack of classmates who demanded that he explain himself. Nonplussed, he said nothing, “inflaming them with a torturous game of racial keep-away.”

Thirty years later, Matthews has dispensed with such reticence. In his kinetic and searching memoir Ace of Spades, he confronts the identity questions that bedeviled him in his youth, telling his story with incisive intelligence and often hilarious irreverence. This unusual combination distinguishes Matthews’s memoir from others to which it will likely be compared, most notably James McBride’s bestseller The Color of Water, which shares its subject matter but not its spirit. McBride, like Matthews, was born to a black father and a white Jewish mother but reared solely by the parent whom he phenotypically resembled least. Both writers describe the contradictions of growing up in a rough-and-tumble city as nerdy types who had a few feckless flirtations with crime but preferred books. Both memoirs are, in part, paeans to the authors’ respective single parents. For all their similarities, however, I can’t seem to remember the part in The Color of Water when McBride humps a lubricated foam mattress or stuffs his shorts with hairnets before gym class to create the illusion of pubic hair. Nor do I recall any anecdote about becoming enraged at a Jewish classmate for crying during a Holocaust video, or one in which he gets mugged and relishes calling the perpetrators “niggers” in front of his black parent. Probably because McBride didn’t go there, as most of us wouldn’t.

Matthews, who recounts all of the above, goes for broke, punctuating his narrative with a series of audacious anecdotes. He’s not merely telling it like it is; he’s testing us: Each outrageous self-revelation seems to dare us to rescind the sympathy he has won elsewhere. But Matthews recognizes that readers who aren’t alienated by his candor will respect him all the more for it.

Or maybe he just likes telling stories. Matthews is a natural at it, with a gift for simile and an expert comic timing that paces even–or perhaps especially–the book’s most freighted moments. Consider, for example, the continuation of the are-you-black-or-white grilling he’s subjected to during his entree into the Baltimore public school system:

As the mob, with me as the cynosure, reached our first-period class, they resorted to a subtler though no less politic tack:

What kind of music…you like?

Even though I (marginally) enjoyed the Jackson Five, that admission might provide partisan ammo to the students most consumed with what I was, so in a panic I threw out names of performers my grandmother liked. That’s how fucked up racism is. What else on earth could have motivated a young boy, first hour in a new school, to throw away any chance at acceptance–forget about cool, we’re talking basic Lord of the Flies do-we-eat-this-kid-or-not survival–­with this reply: Beverly Sills.

Matthews’s comic sensibility leavens Ace of Spades but does not make it light. Some of the facts of his life are irrefutably grim. His mother, Robin, an appealing but mentally ill woman from an Orthodox Jewish family, abandoned him and his father, a radical black journalist named Ralph Matthews Jr., several months after giving birth. They never heard from her again. Growing up, Matthews neither asked for nor was offered any information about his mother, insuring that she–and, by extension, the white world–would become symbolic of all that he wanted and all that his actual (black) life could not provide.

Compounding the absence of little David’s mother is the presence of an evil stepmother: Karen, a blond, blue-eyed “wigger when there was no such word,” who “peppered her speech with that seventies sine qua non noun motherfucker, as in, Look, motherfucker, which she uttered with a regularity most reserve for umm, or so.” Karen beats David, but eventually, mercifully, David’s father gets wise to her abuse, so father and son pack up and head for Baltimore. They move into David’s grandmother’s apartment in a senior citizens’ home, a “wonderland of morbid prophylaxes,” where David is nurtured by his loving grandmother and embarks on a romance with television (“there are worse habits,” he reasons in retrospect, “like Islam or karaoke”). But David’s retreat into this ersatz womb is short-lived, and soon he’s forced to confront the city outside: a poor, “roiling black ghetto.” Baltimore–now that the frail, pale boy must make his way around in it–becomes frankly terrifying: “My earliest years in the idylls of suburbia had been spent in color-blind adoration of my black father, my brother Elijah, my ashy friends with puffy Afros, but now things were different. This was the city, and these were niggers.”

David, from his first day of school on, begins to pass–initially as white and then, more creatively, as a Jew. (There are a couple of priceless moments when, under pressure to explain his swarthiness, he tells his Jewish friends’ parents that he’s half-Palestinian.) Matthews neither defends nor disavows his passing, although he takes the occasional dig at himself for siding with the spineless:

The teachers (black and white) had a brusque, dismissive way of dealing with the black kids, ignoring their raised hands as well as their insolent stares. The tacit suggestion to these kids was that their futures had already been decided for them. The teachers, like me, were not made of much, and just wanted to bet on the white steed of Caucasia.

But this is no tragic mulatto story. Mild self-abasement aside, Matthews does not present his passing as some failure of character. Rather, Baltimore shocks him into consciousness of just how bad blacks have it compared with whites, and the boy negates his blackness to spare himself some of the misery: “Life for me was not a war between black and white, or rich and poor, it was a life sentence that could be commuted only by whiteness, real or imagined.”

James Baldwin observed in Nobody Knows My Name that the question of color can operate “to hide the graver questions of the self.” Matthews, who until adulthood knew virtually nothing about his mother other than that she was white and had abandoned him, grew up pained by questions of who he was and where he came from. Displacing that hurt and anger onto his father–who is not merely black but an unflagging civil rights activist, a friend of Baldwin, Malcolm X and Stokely Carmichael–Matthews acts out by defining himself against him. Not jazz, but John Lennon. Not black, but white. Matthews’s ability to make connections between his mother, his father and his rejection of blackness–without ever minimizing the day-to-day, objective racism that simply made it easier to be white–is a great achievement.

It also makes Matthews’s lack of insight into another realm, his relationship with women, so conspicuous and disappointing. This wouldn’t be such a problem if sex and sexuality weren’t omnipresent in Ace of Spades, but at times the book recalls nothing so much as Portnoy’s Complaint, our protagonist being nearly as preoccupied with his own “battered battering ram of freedom” as Portnoy was with his.

Matthews–who describes not only his first orgasm (a nocturnal emission while his grandmother slept beside him) but his first “bucking orgasm,” his adolescent innovation of masturbating to fuzzy cable and his regimen of self-stimulation while studying for the GED–wins the prize for the most literal coming-of-age story. On autoerotica Matthews is fine, and funny; the trouble is when he writes about actual women to whom he has some sexual connection. Take, for example, his account of losing his virginity:

When she consents to sleep with me that spring before going off to some risible state college in the Midwest, I fuck her with a condom, whose wrapped center, moments before, and unseen by her, I have pierced with a fine sewing needle. You always remember your first.

With that, the chapter ends. A few pages into the next, Matthews describes a fantasy of raping a 10-year-old girl. To be fair, some context: Before sleeping with his first lover, Matthews had a frightening, racist encounter with her two brothers; he is presumably taking his revenge, Eldridge Cleaver-style, on the young lady. As for the child he imagines violating, she’s just called him a nigger. What’s disturbing is not Matthews’s disclosure of misogynistic impulses and actions; it’s his failure to examine them–not merely their immediate provocations but the experiences in which they might be rooted. We’re left to draw our own conclusions, which is not so difficult: In addition to his absent mother and abusive stepmother, Matthews, a self-described “eunuch” during adolescence, was consistently rejected by women until young adulthood. But in a memoir the onus is on the writer to make these connections, and Matthews doesn’t.

If there is another obstacle in our relationship with Matthews as a narrator, it’s that he has spent too many nights spooning the thesaurus. Without question, he is an excellent writer: fluent, robust and with a distinct voice. In this, too, Matthews echoes Philip Roth, with a knack for that appealing admixture of erudition and vulgarity, the high and the low. Yet his language is often unnecessarily obscure–perhaps his stepmother was an “agrestic, toothless ex-harridan,” but perhaps he could find a more accessible way to describe her, too. In these moments, Matthews’s apparent concern that we admire his writing interferes with his ability to make himself known–the chief requirement of his chosen genre. Again, we can speculate about where this comes from: Ace of Spades makes clear the many ways in which Matthews’s identity, including his intellect, was stigmatized when he was younger. But whatever the cause, the effect is alienating, and Matthews comes off as less a pretentious writer than an insecure one.

What redeems these shortcomings is Matthews’s moving portrait of his father, to whom he dedicates the book. From the beginning of Ace of Spades, Matthews is unreserved in his appreciation of his father’s many facets–his passion for justice, his humility, his way with words, his world-weariness, his affection for his son, filtered though it may be through the lens of “cool.” Nevertheless, David’s willingness to be mistaken for white was a rejection of his father (albeit one Ralph understood and, implicitly, forgave). By the end of the book, Matthews is in his 30s and living in New York City; after oscillating between cross-burning cracker and black militant over the course of his life, he describes finally settling into himself. Adulthood also brings about a new dimension in Matthews’s relationship with his father–the ability to talk about emotionally charged subjects once avoided, like his mother. The impression is of Matthews moving toward becoming whole. It’s a process that Ace of Spades not only chronicles but seems to have made possible.