Norman Mailer was one of the most original and powerful writers of the twentieth century, but he never wrote a truly great novel. Despite the great success of his first book, “The Naked and the Dead,” which he wrote at twenty-three, and despite the merits of his second and third novels, “Barbary Shore” and “The Deer Park,” Mailer missed the boat early on, because he never wrote (and seems never even to have considered writing) the book that he was born to write—the bildungsroman of a Maileresque boy in Brooklyn in the nineteen-thirties. Had he written a novel based on his early experiences, it might have done more than launch his career (which “The Naked and the Dead” did quite well); it might have launched his imagination. The power of deep-rooted experience, I suspect, would have given rise to a self-sustaining run of novels. Instead, he sacrificed his literary birthright for the pursuit of experiences that he considered literature-worthy, and he paid a high price to replace it.

J. Michael Lennon’s new biography, “Norman Mailer: A Double Life” (which Louis Menand reviews in the magazine this week), offers a remarkable view of Mailer’s youth. The grandson of a rabbi who struggled in business, the son of a picaresque bookkeeper and an adoring mother, he was a brilliant student and precocious writer. He was also something of a spoiled and fearful child—by his own account, a “physical coward.” Why did Mailer not want to write about the Brooklyn of his youth? Did he hesitate to reveal stories about his parents? (His father, a compulsive gambler, was often in debt, on the edge of legal trouble, and frequently unemployed.) Did he not want to write about his days of sheltered timidity? Was there some other aspect of his early years that he found unspeakable? Was he sparing his family—or himself? Or did he simply look at his background and find it wanting?

Mailer became a celebrity at the age of twenty-five, with the publication, in 1948, of “The Naked and the Dead.” The experience of fame, in Mailer’s own view, transformed his sense of what constituted meaningful life experience. In his 1959 book “Advertisements for Myself,” Mailer discussed the shock of his sudden acclaim and prosperity: “My farewell to an average man’s experience was too abrupt; never again would I know, in the dreary way one usually knows such things, what it was like to work at a dull job, or take orders from a man one hated.” As a result, “there was nothing left in the first twenty-four years of my life to write about.… And so I was prominent and empty, and I had to begin life again”—as if he had exhausted the literary usefulness of his early life, when, in fact, he never really addressed it.

In his review of Lennon’s book, Menand alludes to Mailer’s trouble writing fiction:

He found it hard to make things up. This was a source of endless frustration, since he thought that novel-writing was the higher calling. “I loved journalism,” he once admitted to Lennon, “because it gave me what I’d always been weakest in—exactly that, the story.”

But Mailer shouldn’t have needed to make much up. He left his largest fund of stories—the ones from his first twenty years—untapped. In his reflexive journalism, such as “The Armies of the Night” and “Of a Fire on the Moon”—which is some of his best writing—Mailer wrote copiously about himself, mainly in the present tense, and his self-portraiture is a crucial elements of its appeal. But his trouble with his own past, and with fiction, emerged as a major theme in his writing.

“Advertisements for Myself,” Mailer’s fourth book, is an utterly self-searching, and self-revealing, autobiographical collage that I consider his greatest achievement. He composed it in the late fifties, after having published three novels, and its main subject is his frustrated efforts and ongoing plans to write another, vastly ambitious set of novels (for which, in effect, the book serves as an advertisement or trailer). In “Advertisements,” he looks back over his writing life (starting with collegiate efforts), collecting stories, essays, journalism, occasional pieces, parts of an early version of “The Deer Park” as well as his drastic rewriting of them, and fragments of what he thought would be his subsequent novels (which remained unfinished). He connected these disparate writings with new, interstitial autobiographical commentaries. These interludes established the performative persona that would be the engine for the rest of his life’s work. “Advertisements” is a seminal work of literary postmodernism, as well as a manifesto for the dominance of the first-person voice:

I was a node in a new electronic landscape of celebrity, personality, and status.… I had been moved from the audience to the stage—I was, on the instant, a man—I could arouse more emotion in others than they could arouse in me; if I had once been a cool observer because some part of me knew that I had more emotion than most and so must protect myself with a cold eye, now I had to guard against arousing the emotions of others, particularly since I had a strong conscience, and a strong desire to do just that—exhaust the emotions of others.

This brilliant work of intellectual autobiography is a documentation of, and a substitute for, half a decade of fiction that Mailer didn’t write. His speculative varieties of self-study are also a replacement for a direct narrative exploration of the psychic loam of his youth.