He was a prominent cultural commentator and critic, expressing his often controversial views through his novels, journalism, frequent press appearances, and essays, the most famous and reprinted of which is "The White Negro".

[3][4] His father, Isaac Barnett Mailer, popularly known as "Barney", was an accountant[4] born in South Africa, and his mother, Fanny (née Schneider), ran a housekeeping and nursing agency.

[citation needed] He ended the novel with the words "To be continued" and planned to write a sequel, titled Harlot's Grave, but other projects intervened and he never wrote it.

[42] Mailer's famous essay "The White Negro" (1957) fleshes out the hipster figure who stands in opposition to forces that seek debilitating conformity in American society.

The combination of detached, ironic self-presentation [he described himself in the third person], deft portraiture of literary figures (especially Robert Lowell, Dwight Macdonald, and Paul Goodman), a reported flawless account of the March itself, and a passionate argument addressed to a divided nation, resulted in a sui generis narrative praised by even some of his most inveterate revilers.

Mailer's major new journalism, or creative nonfiction, books also include Miami and the Siege of Chicago (1968), an account of the 1968 political conventions; Of a Fire on the Moon (1971), a long report on the Apollo 11 mission to the moon; The Prisoner of Sex (1971), his response to Kate Millett's critique of the patriarchal myths in the works of Mailer, Jean Genet, Henry Miller and D.H. Lawrence; and The Fight (1975), an account of Muhammad Ali's 1974 defeat in Zaire of George Foreman for the heavyweight boxing championship.

In addition to his experimental fiction and nonfiction novels, Mailer produced a play version of The Deer Park (staged at the Theatre De Lys in Greenwich Village in 1967),[57] which had a four-month run and generally good reviews.

[61] In 1987, he adapted and directed a film version of his novel Tough Guys Don't Dance starring Ryan O'Neal and Isabella Rossellini, which has become a minor camp classic.

[63][64] Although Leone would pursue other writers shortly thereafter, elements of Mailer's first two drafts of the commissioned screenplay would appear in the Italian filmmaker's final film, Once Upon a Time in America (1984), starring Robert De Niro.

[66] In 1982, Mailer and Lawrence Schiller would collaborate on a television adaptation of The Executioner's Song, starring Tommy Lee Jones, Roseanna Arquette, and Eli Wallach.

The male lead role, an Irish-American streetfighter who finds redemption in the ring, was to be Brendan Fraser, and it was also to star Halle Berry, Anthony Quinn, and Paul Sorvino.

[72] His own biographer, J. Michael Lennon, explains that Mailer would use "himself as a species of divining rod to explore the psychic depths" of disparate personalities, like Pablo Picasso, Muhammad Ali, Gary Gilmore, Lee Harvey Oswald, and Marilyn Monroe.

In the late 1950s and throughout the 1960s and 1970s, his work mingled autobiography, social commentary, history, fiction, and poetry in a formally original way that influenced the development of New Journalism.

In Miami and the Siege of Chicago (1968), he explained his view of "politics-as-property", likening a politician to a property holder who is "never ambivalent about his land, he does not mock it or see other adjacent estates as more deserving than his own."

[84] In September 1961, Mailer was one of 29 original prominent American sponsors of the Fair Play for Cuba Committee organization with which John F. Kennedy assassin Lee Harvey Oswald was associated in 1963.

[93] Mailer "foresaw the city, its independence secured, splintering into townships and neighborhoods, with their own school systems, police departments, housing programs, and governing philosophies.

In The White Negro (1957), Mailer introduced his "Hipster" archetype as an individual who uses violence as a form of rebellion and self-discovery, confronting societal hypocrisy and embracing primal impulses.

This perspective underlies much of his work, particularly An American Dream (1965), in which protagonist Stephen Rojack commits violent acts that symbolize a radical break from societal constraints, reflecting Mailer's existential philosophy.

In The Naked and the Dead (1948), Mailer contrasts the individual struggles of soldiers with the dehumanizing machinery of war, highlighting the tension between personal autonomy and authoritarian control.

[105] His distrust of middle-class values and suburban complacency is a recurring motif in his works, where he often depicts the "outsider" as a figure of integrity against societal pressures to conform.

His book Miami and the Siege of Chicago (1968) documents the 1968 Democratic National Convention, where he critiques the establishment's moral failings and the inherent compromises of political power.

In "Superman Comes to the Supermarket" (1960), he critiques the rise of consumer culture and its impact on political leadership, arguing that America needs a leader with the “existential courage” to confront societal decay.

In The Presidential Papers (1963), he reflected on Kennedy's presidency, voicing concerns over the tendency of political power to prioritize public image over substantial existential action.

Millett critiques Mailer as a proponent of a "virility cult", emphasizing his portrayal of sex as an expression of power and violence, and he positions male sexuality as combative and inherently dominating.

[119] Critics like Joyce Carol Oates argued that Mailer’s perspective, while ostensibly reverent toward femininity, ultimately "dehumanized" women by reducing them to carriers of biological destiny rather than as complex individuals with aspirations beyond motherhood and sexuality.

In addition – and notable for such a prominent mainstream American writer of his generation – Mailer, throughout his work and personal communications, repeatedly expresses interest in, includes episodes of, or makes references to bisexuality or homosexuality.

[122] Mailer focused on jazz as the ultimate expression of African-American bravado, and he represented musical figures such as Miles Davis in works including An American Dream.

After hosting a party on Saturday, November 19, 1960, Mailer stabbed Adele twice with a two-and-a-half inch blade that he used to clean his nails, nearly killing her by puncturing her pericardium.

[148] As the show began taping a visibly belligerent Mailer, who admitted he had been drinking, goaded Vidal and Cavett into trading insults with him on-air and referred to his own "greater intellect".

[169] Reviewer Nicole DePolo writes that Susan Mailer, a psychoanalyst, provides sharp insights about her father in "crisp, vibrant prose that captures the essence of moments that are both remarkable and universally resonant".