THERE’S SOMETHING ALMOST IDYLLIC about the killers and drug dealers depicted in Criminals: My Family’s Life on Both Sides of the Law, Robert Anthony Siegel’s account of his New York City childhood as the son of an unscrupulous defense attorney. Crooks of a distinctly 1970s Manhattan vintage, the men Siegel’s father represents and reveres rarely inspire the author to consider the societal and cultural pressures impelling their lives of crime. Whether that’s indicative of their commitment to cinematic violence for its own sake or a failure of empathy on the part of the author, the book alights upon a time before the inequities of the justice system interrupted age-old modes of storytelling. Whereas contemporary discourse surrounding American criminality focuses on the gap between ethics and enforcement, immoderate sentencing for nonviolent transgressions, and border patrollers rounding up brown families, Siegel looks upon the rogues’ gallery at his doorstep and finds prisoners of their own devices.

Siegel, an essayist, art critic, and two-time novelist, is encouraged by his parents from a young age to seek romance and humanity in the parade of miscreants traipsing through his childhood home. Yet he’s mostly flustered by them, disdainfully envious of the way they consume his parents’ affections. In his prime, Siegel’s father represents clients who are practically rock stars: A-list Hells Angels, heavyweight cocaine traffickers, and jet-set artists with predilections for mischief. Glossing over their unseemly qualities, Siegel’s father and mother both focus on the clients’ tastes and educations, their capacities for culture, conversation, and art appreciation. Often, however, that’s all Siegel’s parents can agree upon.

Relayed in 16 achronological essays interspersed with brief, elegiac prose interludes, Criminals executes a perceptive portrait of a marriage, the weirdness of a couple with profoundly disparate values. Siegel’s delicate narration conveys these flawed adults as seen through the indiscriminate eyes of a child, yet locates their shortcomings as parents. There’s ample consideration of the ways in which the sins of the father are visited upon the children, who are often deployed by the parents as soldiers in their war against one another.

A fragile, slovenly man of voracious appetites, depressive tendencies, and an all-encompassing need for validation, Siegel’s father argues that his vocation is virtuous and downright patriotic. During gloomier spells he stews on the couch for days at a time, manically dissecting his financial woes, surrounded by takeout trays.

The antithetical whimsy of Siegel’s father is best captured by an anecdote in which a neighbor accosts him for defending killers in court. In response, the attorney takes poetic license with Dachau survivor Martin Niemöller’s “First they came…”:

I didn’t say anything when they came for the drug addict, because I wasn’t a drug addict. I didn’t say anything when they came for the street walker, because I wasn’t a street walker […] I didn’t say anything when they came for the thief, because I wasn’t a thief. So there was nobody left when they came for me …

A son of the Great Depression Borscht Belt, Siegel’s father no doubt appreciates Niemöller’s condemnation of Holocaust enablers. What goes unmentioned to their indignant neighbor is that Mr. Siegel defends Hells Angels who traverse the city outfitted in Nazi regalia. “It allowed us to go on believing that we had made no mistakes, that there was nothing wrong in living with criminals in our strangely starstruck way,” the author reflects. His father’s career ultimately spirals after a loose-lipped former client lands him a short stint in a Connecticut correctional facility, dooming him to ignominious work as a public defender once he’s released.

Siegel’s mother, on the other hand, is hell-bent on developing her children’s taste for high society even if they grow up surrounded by scoundrels. Ashamed of her humble Brooklyn beginnings, she drags young Robert to the ends of the earth through museums, ancient ruins, and gourmet restaurants. Desperate to prove to them — or perhaps herself — the existence of beauty in art, cuisine, and architecture, she is equally obsessed with affirming that her family is better than their source of income. She is the book’s most complex character, one minute daintily chewing through Michelin-starred menus, the next counting dirty money out of a paper bag.

Robert, a meek young man, spends his childhood ricocheting between his strong-willed parents, alternately vying for dissonant approval. Tagging along to client meetings with his father, he finds himself unsupervised for terrifying hours at a time in genuine houses of sin. On afternoons at MoMA with his mother, “I wanted to become an artist,” he recalls, “but what I really wanted, on some unconscious level, was to become a painting, so my mother could look at me with the same intense expression she had when we stood in front of a Rothko or a De Kooning: rapt, open, wondering.”

Siegel’s memoir is not a revenge text: he loves his parents far too much for that. But he remembers them as bumbling and inconsiderate, fixated on status and sophistication. These qualities drive Robert to seek fellowship in distant havens. His enthusiasm for judo propels him to enroll in Japanese language classes, and he later escapes to Tokyo for a lonely undergraduate year abroad. Returning to the scenes of his youth as a directionless Harvard grad, he notes, “I had no idea what to do next, no idea how grown-ups generally put a life together so that they don’t look shameful to other people.”

The most compelling essays are reflections of Siegel’s keenly sensitive eye, discerning tension and pathos in moments others would reasonably bypass. There’s a faint through-line traced from his parents’ neuroses to Robert’s quietly tortured soul, yet Criminals is not overladen with self-pity. While the chapters recounting the author’s young adulthood tend toward the morose, Siegel’s reminiscences evince a wayward search — for ideals, for self-worth, for simultaneous belonging and independence — without ever admitting how melancholy he really was.

The overall achronological structure, which further extends to the nested anecdotes in many of the essays, makes for a dreamlike, wistful ambience. The reveals are less narrative than emotional as the past invades the future in unpredictable ways. While this format can make for a lifelike mosaic, it sags as a consolidated read. There’s a sense of thematic redundancy enhanced by repetition of episodes across different essays, which accentuates the second half’s less resonant chapters.

At times Robert reads like a background character in his own first-person narratives, resulting in dispatches that feel more reported than lived. Brilliant observations are rendered in a clinical fashion, such that he seems to lack agency even in his life’s defining hours. In essays about Japan, academia, and a sudden embrace of vegetarianism, he is a mound of willing clay begging to be molded by whichever monk, pimp, or professor arrives for dinner. So few of the essays cast his parents in a becoming light that his unflagging love and dispassionate reactions are almost disorienting, a logical anger never surfacing.

Still, for a memoir only passingly concerned with its narrator, Siegel’s voice and incisive scrutiny result in standalone triumphs. Where “Everyone Wants to Be a Hells Angel” might have subsisted on name-dropping and shock value, Siegel scours his experience to see past the gang’s bigotry and brutality to their anarchic appeal. For his father, the Angels represent an escape from middle-class doldrums, freedom from the drudgeries of fatherhood, obesity, and Judaism. At his funeral, Robert encounters Sandy Alexander, former president of the Angels’ New York chapter and a fearsome figure from his childhood. “He seemed broken more than anything else,” he writes, “and that seemed to me a perfectly natural response to life.”

A later essay titled “Homesteaders” finds Robert and his brother considering legal action against a con artist who’s swindled their rent money. In their investigation, the brothers find a box of correspondence confirming that the man was not only broke and facing prosecution, but HIV positive. An old letter in which he begs clemency from a judge floors Robert, who writes:

Before my father was sentenced, I had written a letter like this, asking for mercy. I’d fantasized about writing an angry letter, telling how he had been railroaded by overzealous prosecutors, how his livelihood had been destroyed over the course of an investigation that was more like a one-sided war of attrition, a carpet bombing. I wanted to write about how we had suffered. But I didn’t write any of that. I wrote about what a good father he was and how much I loved him and would miss him if he had to go to prison. I wrote it in a sort of blank state, watching my hand move, as if I weren’t a whole person but just a collection of limbs.

I did not understand mercy then. I was ashamed to ask for it. I was angered by my own desire to give it.

Criminals should find a ready audience of readers who made hits of City on Fire, The Fortress of Solitude, and Tuesday Nights in 1980 — colorful tributes to Koch-era New York that purveyed dystopian dreamscapes of the city just before the ravages of AIDS and crack. But Criminals isn’t a panoramic romp so much as a poetic evocation of Siegel’s adolescent mind, conflicted accounts of feeling powerless to soothe the languishing personalities around him. It is, at base, about forms and degrees of yearning. Siegel’s family, their associates, and their city are populated by reprobates willing to risk relative comfort to sate bottomless hunger. As they stumble toward the 21st century, catastrophe dulls into bearable decline and acceptance of past mistakes. Witnessing such a sharp writer make peace with his remarkable origins is a thrill even in the memoir’s weaker moments.

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Pete Tosiello’s literary criticism has appeared in theWashington Post, the Los Angeles Times, The Kenyon Review, The Village Voice, The Outline, the Washington City Paper, The Awl, and Full Stop.