LOS ANGELES — Gore Vidal, the author, playwright, politician, and commentator whose novels, essays, plays, and opinions were stamped by his immodest wit and unconventional wisdom, died Tuesday at age 86, his nephew said.

Mr. Vidal died at his home in the Hollywood Hills of complications from pneumonia, Burr Steers said. Mr. Vidal had been living alone in the home and had been sick for “quite a while,” he said.

Along with such contemporaries as Norman Mailer and Truman Capote, Mr. Vidal was among the last generation of literary writers who were also genuine celebrities — fixtures on talk shows and in gossip columns, personalities of such size and appeal that even those who hadn’t read their books knew who they were.

His works included hundreds of essays; the best-selling novels ‘‘Lincoln’’ and ‘‘Myra Breckenridge”; the groundbreaking ‘‘The City and the Pillar,’’ among the first novels about openly gay characters; and the Tony-nominated play ‘‘The Best Man,’’ revived on Broadway in 2012.

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Tall and distinguished looking, with a haughty baritone not unlike that of his conservative arch-enemy William F. Buckley, Mr. Vidal appeared cold and cynical on the surface. But he bore a melancholy regard for lost worlds, for the primacy of the written word, for ‘‘the ancient American sense that whatever is wrong with human society can be put right by human action.’’

Mr. Vidal was uncomfortable with the literary and political establishment, and the feeling was mutual. Beyond an honorary National Book Award in 2009, he won few major writing prizes, lost both times he ran for office, and initially declined membership into the American Academy of Arts and Letters, joking that he already belonged to the Diners Club. (He was eventually admitted, in 1999).

But he was widely admired as an independent thinker — in the tradition of Mark Twain and H. L. Mencken — about literature, culture, politics and, as he liked to call it, ‘‘the birds and the bees.’’ He picked apart politicians, living and dead; mocked religion and prudery; opposed wars from Vietnam to Iraq; and insulted his peers like no other, once observing that the three saddest words in the English language were ‘‘Joyce Carol Oates.’’ (The happiest words: ‘‘I told you so”).

Mr. Vidal had an old-fashioned belief in honor, but a modern will to live as he pleased. He wrote in the memoir ‘‘Palimpsest’’ that he had more than 1,000 ‘‘sexual encounters,’’ nothing special, he added, compared to the pursuits of such peers as John F. Kennedy and Tennessee Williams.

Mr. Vidal was fond of drink and said that he had sampled every major drug, once. He never married and for years shared a villa in Ravello, Italy, with companion Howard Austen.

Mr. Vidal would say that his decision to live abroad damaged his literary reputation in the United States. In print and in person, he was a shameless name dropper.

He dined with Orson Welles in Los Angeles, lunched with the Kennedys in Florida, clowned with the Newmans in Connecticut, drove wildly around Rome with a nearsighted Tennessee Williams, and escorted Mick Jagger on a sightseeing tour along the Italian coast. He campaigned with Eleanor Roosevelt and Harry Truman. He butted heads, literally, with Mailer. He helped director William Wyler with the script for ‘‘Ben-Hur.’’ He made guest appearances on everything from ‘‘The Simpsons’’ to ‘‘Rowan and Martin’s Laugh-In.’’

Mr. Vidal formed his most unusual bond with Oklahoma City bomber Timothy McVeigh. The two exchanged letters after Mr. Vidal’s 1998 article in Vanity Fair on ‘‘the shredding’’ of the Bill of Rights and their friendship inspired Edmund White’s play ‘‘Terre Haute.’’

Mr. Vidal also bewildered his fans by saying the Bush administration likely had advance knowledge of the Sept. 11, 2001, attacks; that McVeigh was no more a killer than Dwight Eisenhower and that the United States would eventually be subservient to China, ‘‘The Yellow Man’s Burden.’’

A longtime critic of American militarism, Vidal was, ironically, born at the United States Military Academy in West Point, N.Y., his father’s alma mater. His grandfather, Thomas Pryor Gore, was a US senator from Oklahoma. His father, Gene, served briefly in President Franklin Roosevelt’s administration and was an early expert on aviation.

Mr. Vidal was a learned, but primarily self-educated man. Classrooms bored him. He graduated from the elite Phillips Exeter Academy, but then enlisted in the Army and never went to college. His first book, the war novel ‘‘Williwaw,’’ was written while he was in the service and published when he was just 20.

Orville Prescott of The New York Times praised Mr. Vidal as a ‘‘canny observer’’ and ‘‘Williwaw’’ as a ‘‘good start toward more substantial accomplishments.’’ But ‘‘The City and the Pillar,’’ his third book, apparently changed Prescott’s mind. Published in 1948, the novel’s straightforward story about two male lovers was virtually unheard of at the time and Mr. Vidal claimed that Prescott swore he would never review his books again. (The critic relented in 1964, calling Mr. Vidal’s ‘‘Julian’’ a novel ‘‘disgusting enough to sicken many of his readers”).

Unable to make a living from fiction, at least when identified as ‘‘Gore Vidal,’’ he wrote a trio of mystery novels in the 1950s under the pen name ‘‘Edgar Box’’ and also wrote fiction as ‘‘Katherine Everard’’ and ‘‘Cameron Kay.’’ He became a playwright, too, writing for the theater and television. The political drama ‘‘The Best Man’’ was later made into a movie, starring Henry Fonda, was revived on Broadway in 2000 and again in 2012. Paul Newman starred in ‘‘The Left-Handed Gun,’’ a film adaptation of Vidal’s ‘‘The Death of Billy the Kid.’’

Mr. Vidal also worked in Hollywood, writing the script for ‘‘Suddenly Last Summer’’ and adding a subtle homoerotic context to ‘‘Ben-Hur.’’

In the 1960s, Mr. Vidal increased his involvement in politics. In 1960, he was the Democratic candidate for Congress in an upstate New York district, but was defeated despite Eleanor Roosevelt’s active support and a campaign appearance by Truman. (In 1982, Vidal came in second in the California Democratic senatorial primary). In consolation, he noted that he did receive more votes in his district in 1960 than did the man at the top of the Democratic ticket, John F. Kennedy.

Thanks to his friendship with Jacqueline Kennedy, with whom he shared a stepfather, Hugh Auchincloss, he became a supporter and associate of President Kennedy, and wrote a newspaper profile on him soon after his election.

Before long, however, he and the Kennedys were estranged, touched off by a personal feud between Mr. Vidal and Robert Kennedy apparently sparked by a few too many drinks at a White House party. By 1967, the author was an open critic, portraying the Kennedys as cold and manipulative in the essay ‘‘The Holy Family.’’ Mr. Vidal’s politics moved ever to the left and he eventually disdained both major parties as ‘‘property’’ parties.