Through J. Michael Lennon's meticulous Norman Mailer: A Double Life, you get a sense of the writer's manic energy, his narcissism, and his fierce moral seriousness as an opponent of power. Lennon, literary executor of Mailer's estate and his friend, distills Mailer's 60-year career into his 10 best books.

In 1948, a 25-year-old World War II veteran leaped into prominence with a number one best-selling novel about his combat experience in the Pacific, The Naked and the Dead. Over the next 60 years he wrote across a range of genres: biography and memoir, a column in the Village Voice, crime and sports narratives, poetry and short stories, several film scripts, and ten more novels of astounding variety. Along with Gay Talese, Tom Wolfe and Joan Didion, he was one of the founders of the New Journalism, which adapted fictional techniques to nonfiction. A nearly ubiquitous media figure and intellectual provocateur, he performed on the public stage more brilliantly than any writer since Mark Twain. But he was also a machine of literary production, producing 44 books, all told. He may be the only major American writer with one or more best-selling books in each of seven consecutive decades.

There has been debate on whether Mailer’s greatest achievements are in fiction or nonfiction, but it is clear that he was ambidextrous, so to speak, excelling in both. I lean slightly toward his nonfiction in my picks.

1. The Executioner’s SongAn immense panoramic nonfiction novel with over 300 characters that recreates the last nine months of Utah murderer Gary Gilmore. Relying heavily on the actual words of those involved (taken from 15,000 pages of interviews), Mailer depicts Gilmore’s Romeo-and-Juliet love affair with a young mother, Nicole Baker (both attempted suicide), and details the legal struggle between those who sought Gilmore’s reprieve and those who opposed it—the latter led by Gilmore, who insisted that his death sentence be carried out. He won and in January 1977 got four bullets through the heart—the first execution in the U.S. in ten years. Lawrence Schiller, Gilmore’s advisor, media spokesman, literary executor and the distributor of his ashes, holds the narrative together, and stands in for Mailer, who tells the story anonymously in what he called “a quiet voice from the other side of the hill.” He won his second Pulitzer for this book.

2. The Armies of the NightDescribing himself in the third person, Mailer draws on the techniques of the novelist, the journalist, and the historian to depict a divided nation. Generally considered to be one of the glories of the New Journalism, the narrative is a sharply observed account of the October 1967 anti-Vietnam War March on the Pentagon, the culmination of three days of protest in the nation’s capital. Mailer, the half-comic, half-heroic protagonist, was arrested and jailed for his part in the March. Armies also contains a brilliant portrait of poet Robert Lowell, Don Quixote to Mailer’s Sancho Panza. The book won both a Pulitzer and the National Book Award.

3. An American DreamWritten month by month for serial publication in Esquire, this dread-soaked 1965 novel about a psychology professor who murders his high society wife shows Mailer at the height of his metaphoric power. Narrated by the protagonist, Steven Rojack, the focus is on his haunted conscience, and his operatic struggle with his wife’s father, Barney Oswald Kelly, one of the great villains in modern American literature. President Kennedy has a cameo role in the story, which is set in the wealthiest section of New York City just months before his assassination. Joan Didion called the novel “the only serious New York novel since The Great Gatsby.”

4. Advertisements for MyselfThis 1959 miscellany contains samples of all Mailer’s earlier work stretching back to short stories written in college, as well as his endlessly reprinted essay about hipsters living in the New York demimonde, “The White Negro.” Excerpts from his Village Voice column are included, as is a new short story, “The Time of Her Time,” which details the sexual adventures of a Village stud, Sergius O’Shaugnessey. The collection is held together by bursts of italicized prose—part confession, part tirade, part visionary testament—recounting the ups and downs of his literary career and written in an edgy, slangy, sardonic style.

5. Harlot’s Ghost—Mailer’s longest book (1310 pages) is a spy novel. Like a long freight train, his story of WASP intelligence agents in war and peace snakes through upper-class American life (Mt. Desert, Yale, the 21 Club), picks up speed as it moves through international intrigues in Europe, slows to a crawl in Uruguay, and then accelerates rapidly as it moves through the CIA’s attempts to poison Castro, its failed invasion at the Bay of Pigs and the Cuban missile crisis. Some of J.F.K.’s extramarital love affairs comprise another strand of the novel’s loosely braided narrative of deception, loyalty, betrayal and heroism. Despite its flaws—a 260-page digression set in Uruguay, and characters who spout their author’s favorite ideas—the novel is still a magnificent, if incomplete, achievement, reminiscent of an unfinished cathedral. It ends with the words: “To be continued,” a promise never fulfilled.

6. The Naked and DeadSet on the fictional island of Anopopei, where a Prospero-like American general attempts to defeat a stubborn Japanese force, Mailer’s novel vies with James Jones’ A Thin Red Line as the finest fictional depiction of World War II combat. Using the notes he collected on more than a hundred soldiers he served with, Mailer demonstrates his considerable powers of characterization and ability to portray every misery of jungle warfare.

7. The Fight—The definitive account of one the most dramatic prizefights in history, “The Rumble in the Jungle,” Muhammad Ali’s epic championship bout with George Foreman in Kinshasa, Zaire in 1974, also provides a brilliant evocation of Congolese n’golo, or life force. The supporting cast includes Hunter Thompson and George Plimpton. Mailer’s last major effort at self-portraiture.

8. Why Are We in Vietnam?—Set in the peaks of the Brooks Range in Alaska, Mailer’s 1967 novel of big-game hunting and communing with the wilderness is one of his briefest, a mere 200 pages. Narrated in a hip, obscene fashion by a mysterious narrator, the novel also contains an implicit anti-war message. Although he grew up in cities, Mailer’s sensitivity to nature’s resonances must be considered as one of his most commanding skills.

9. Marilyn—Mailer’s first collaboration with Lawrence Schiller, and his first full-length biography (1973), examines one of Hollywood’s most glittering icons. He explores the tragicomedy of Monroe’s many love affairs, with emphasis on those with Joe DiMaggio and Arthur Miller. Monroe’s inner life, Mailer admits, resembles his own in several ways, especially the interplay of identity and ambition. Critiques of her major films are interspersed.

10. The Time of Our Time—Another monster of 1300 pages, TOOT, as Mailer called it, contains 130-plus excerpts from his books arrayed chronologically so as to deliver a portrait of the U.S. from World War II through the Clinton Administration. The Cold War is the volume’s defining event. Admittedly written under the influence of John Dos Passos’ multi-volume novel, U.S.A., Mailer’s collection picks up where its predecessor leaves off. The cavalcade of characters includes fictional and historical figures from twenty of Mailer’s books, yet it somehow hangs together.