Mr. Holton helped break the domination of Virginia politics by the Byrd political organization, which ardently supported racial segregation, and his election as governor in 1969 made him the first Republican to hold statewide office in Virginia in the 20th century.

He persuaded the legislature to raise the income tax and the gasoline tax, and he used the money for environmental protection, higher education and transportation projects. But he called his work on race relations “the greatest source of satisfaction and pride for me.”

In his inaugural address from the steps of the Capitol of the old Confederacy, Mr. Holton quoted Abraham Lincoln in calling for an open society that operates “with malice toward none, with charity for all.”

“Let our goal in Virginia be an aristocracy of ability, regardless of race, color or creed,” he said.

Mr. Holton opposed busing as a tool to achieve integration, but when a federal appeals court affirmed the order to require busing in Richmond’s schools in the summer of 1970, the Holtons decided as a family to participate, even though the governor’s mansion was not technically in the area covered by the order.

He drew international attention on the first day of school in September 1970, eight months after his inauguration, when he escorted his daughter Tayloe to Kennedy High School. His wife was enrolling two of the couple’s younger children at a mostly Black middle school.

“What I did, and what I tried to emphasize, was: Look, the system requires an answer, and the answer comes from the courts, and if the courts give this answer, then you’ve got to comply with it,” Mr. Holton said in an interview for this obituary. “That’s fundamental to the republic. . . . And that’s what made me feel so good as I walked up to that school.”

Mr. Holton’s election victory — his only one at any level — also made him the first of the progressive New South governors, to be followed a year later by Democrats Jimmy Carter of Georgia, Dale Bumpers of Arkansas, Reubin Askew of Florida and John West of South Carolina.

But even before Mr. Holton’s term was up, the Virginia GOP had moved to his right and the governor openly split with Richard M. Nixon over the president’s Southern strategy of building a Republican majority by winning over conservative Southern Democrats.

“If he could ever have gotten another Republican nomination, he would have been back in office,” University of Virginia political scientist Larry Sabato said of Mr. Holton. “The party wouldn’t nominate him. They had gone well to the right of Linwood Holton and kept moving.”

Abner Linwood Holton Jr. was born Sept. 21, 1923, in Big Stone Gap, Va., in the southwestern part of the state where his father was president of a coal mine railroad.

He graduated in 1944 from Washington and Lee University in Lexington, Va., and served in the Navy in the Pacific during World War II. He returned to Virginia after obtaining a degree from Harvard Law School in 1949.

A few years later, he met Virginia “Jinks” Rogers, a CIA intelligence analyst from a prominent Democratic Virginia family, on a blind date. They wed in 1953. In addition to his wife, of Kilmarnock, survivors include four children, Tayloe Loftus of Cazenovia, N.Y., Anne Holton of Richmond, A. Linwood “Woody” Holton III of Columbia, S.C., and Dwight Holton of Portland, Ore.; a sister; and 10 grandchildren.

As Mr. Holton began gravitating toward GOP politics in the 1950s, Virginia was in the middle of the 40-year reign of Harry F. Byrd Sr., who as governor and then as senator commanded the dominant Democratic Party with strict adherence to fiscal and social conservatism. Virginia’s taxes were minimal, as was its support for education, roads, mental health care and other services.

In the 1950s, dissatisfaction with the Byrd organization, notably in the cities and suburbs that stretched from Northern Virginia to Norfolk. New residents were eager for more services, and the popularity of Republican President Dwight D. Eisenhower brought many voters to the party.

Mr. Holton became a leader among the state party’s moderates and narrowly lost a 1955 race for a House of Delegates seat from Roanoke by campaigning for compliance with the previous year’s U.S. Supreme Court decision in Brown v. Board of Education ordering an end to segregation of public schools.

Virginia’s governor at the time, Thomas B. Stanley, took the same position at first, but Byrd decided instead on a policy of “massive resistance” to integration.

Mr. Holton worked on building the Republican organization as a party official and during his low-budget race for governor in 1965, when he lost to Democrat Mills E. Godwin Jr. He had the campaign support of Eisenhower and former vice president Nixon. Mr. Holton, in turn, was an early leader of Nixon’s successful 1968 campaign for president.

The next year, with Democrats badly divided, Mr. Holton received help from the state’s major union and Black organizations as well as Nixon to beat William C. Battle in the race for governor. The Republican Party had arrived in Richmond.

“When this man was elected governor in 1969, I felt — like most loyal Democrats — that the world had come to an end,” Gerald L. Baliles, a later governor, said at a 1999 conference on Mr. Holton’s term.

With just a handful of fellow Republicans in the General Assembly, Mr. Holton established friendships with moderate Democratic lawmakers and persuaded them on some key initiatives.

“He had a productive career, and the General Assembly was 85 percent Democratic, but that actually helped him,” Sabato said. “They didn’t see him as a threat. They viewed him as a fluke. . . . He was much more than a transitional figure. He helped Virginia move into the modern era on race and lots of other things.”

In an effort to stop pollution of Virginia waterways, Mr. Holton won an increase in the income tax to upgrade sewage treatment plants. He also instituted a Cabinet form of government and appointed minorities, Democrats and even out-of-state experts to important jobs in his administration.

One such appointment was of Ernie Fears Sr., the Norfolk State University basketball coach and athletic director, as director of Virginia’s Selective Service program. “Two-thirds of the kids that we were drafting for the Vietnam War were Black,” Mr. Holton said. “So I wanted somebody to integrate that system and found out that Ernie was the guy I wanted.”

After leaving office in 1974, Mr. Holton briefly served as assistant secretary of state for congressional relations in the Nixon administration. He became a partner in the law firm Hogan & Hartson in Washington and Richmond and said he was not “one of the book lawyers,” acting instead as a dealmaker and a lobbyist.

One deal he made, at the request of then-Transportation Secretary Elizabeth Dole, put Washington National and Dulles International airports under local control. The two airports had been the only ones in the nation run by the federal government, and Mr. Holton lobbied members of Congress for two years to create the airports authority.

“If we had not assured them that they would have parking right close to the gate, Congress wouldn’t have passed it,” he said.

As chairman of the Metropolitan Washington Airports Authority, Mr. Holton helped push for modernizing the airports and expanding Dulles while responding to the concerns of Washington-area residents. But he had limited sympathy for people who moved near the airports and then complained about the noise. As a ­resident of McLean, Va., he used the roar of the jets from National to cover up his deliberate violation of Fairfax County firearms ordi­nances.

Mr. Holton said that, like his father, he liked to garden, and he was frustrated because he realized that the squirrels were getting all the fruit from the peach tree he had planted in his front yard. So he got out his bird gun.

“I would sit outside my garage and wait for the noise of the planes overhead,” he said. “Altogether that fall, I killed 13 squirrels and got three bushels of peaches.”

Before Mr. Sahl, wisecracks about government and Washington were little more than glib asides with no attempt at the jugular. For the most part, comedians avoided topics that might alienate escapist-minded radio, TV and nightclub audiences and stuck to safer material about mothers-in-law or nagging spouses.

By contrast, Mr. Sahl dove headfirst into the divisive politics and tumult of his time — from the nuclear arms race to segregation — with erudite outrage, a finely tuned sense of the absurd and a high tolerance for risk. Referring to his more genial comic forebear, Time magazine described him in a 1960 cover story as “Will Rogers with fangs.”

Mr. Sahl developed a trademark look — a V-neck sweater and loafers, befitting a graduate student — and he carried onstage the rolled-up newspapers whose headlines he had plundered for inspiration. Having honed his style in seedy San Francisco bars and coffeehouses, he riffed in knowing argot about presidential politics, Cold War paranoia, institutionalized religion and neurotic relationships between the sexes.

During the height of Sen. Joseph McCarthy’s anti-communist witch hunts, which ensnared numerous entertainment figures, among other targets, Mr. Sahl took the position that “McCarthy doesn’t question what you say as much as your right to say it.”

He painted President Dwight D. Eisenhower as a blandly avuncular, distracted, golf-obsessed leader. Amid the 1957 racial integration showdown in Little Rock, Mr. Sahl joked that Eisenhower considered walking a Black girl to school but could not decide “whether or not to use an overlapping grip.”

He mocked talk of the “missile gap” during the 1960 presidential campaign, wryly jesting, “Maybe the Russians will steal all our secrets, then they’ll be three years behind.” And he spoke facetiously in favor of capital punishment, observing, “You’ve got to execute people. How else are they gonna learn?”

With more sophistication than a string of staccato one-liners, his jokes formed a free-flowing narrative punctuated by references to political and diplomatic leaders including Secretary of State Christian A. Herter, Cold War hot spots such as Malta and Pakistan, and legislation such as the Taft-Hartley Act.

In one discursive story about Eisenhower’s travels abroad, Mr. Sahl said that White House press secretary James C. Hagerty grew testy when reporters asked when the president might visit Russia.

“Hagerty was quoted as saying, ‘Don’t ask me, I’m not God,’ ” Mr. Sahl said. “Somewhat out of proportion to the question.”

In “Seriously Funny,” a book about rebel comics of the 1950s and 1960s, Gerald Nachman explored the novelty of Mr. Sahl’s intellectual, explanatory style and his Ivy League wardrobe.

“Pre-Sahl was a time in which comedians, clad like bandleaders in spats and tuxes, announced themselves by their brash, anything-for-a-laugh, charred-earth policy and by-the-jokebook gags,” Nachman wrote. “Sahl challenged and changed all that simply by the comic device of being himself and speaking his mind onstage.”

At the end of his shows, Mr. Sahl would ask, “Is there anyone here I haven’t offended?”

Playboy magazine publisher Hugh Hefner became an admirer of Mr. Sahl’s humor and promoted him as an exemplar of cool sophistication. The comedian performed on Broadway and in Playboy Clubs, acted in films, recorded popular comedy albums and appeared on a bevy of late-night and other comedy shows.

He was regarded as a pathfinder for the more topical, personal or offbeat styles honed by Lenny Bruce, Bob Newhart, Mike Nichols, Dick Gregory, George Carlin, Joan Rivers and Mark Russell.

In 1954, a 19-year-old Woody Allen saw Mr. Sahl perform at a New York nightclub and for years mimicked his delivery style. “He was the best thing I ever saw,” Allen once said. “He was like Charlie Parker in jazz. . . . He totally restructured comedy.”

Behind Mr. Sahl’s humor lay a deep concern for American democracy, and his onstage probing was the antithesis of the cheap laugh. He sometimes warmed up crowds for his friend Dave Brubeck, but the jazz pianist complained that “he demands so much of an audience that it hasn’t the strength for anyone else.”

His high-minded material itself invited satire. In the early 1970s, Carlin portrayed a manic Mr. Sahl uncorking a ludicrous rant about the Arab League, student riots in Japan, Eisenhower watching a movie in Manila and the role of Asian religions in ecclesiastical history.

By then, Mr. Sahl’s career had fallen into decline, a development owed almost wholly to his nonstop ribbing of President John F. Kennedy and his obsession with his assassination in 1963.

Mr. Sahl had admired Kennedy and even contributed one-liners to his 1960 campaign speeches. But, fiercely independent and vowing to make any White House occupant the butt of his humor, he let loose when Kennedy won. He joked about Kennedy’s wealthy father influencing the election outcome (“You’re not allowed one more cent than you need to buy a landslide”), the Kennedy preoccupation with communist Cuba, and the new president’s rumored mafia connections.

He incurred the wrath of Kennedy intimates and said his livelihood was threatened. Many nightclubs, fearing tax audits, stopped booking him. Some liberals in his fan base, having grown accustomed to gibes about Eisenhower and Nixon, abandoned him.

Mr. Sahl plowed ahead and made an even more radical shift after the assassination.

Deeply shaken by the killing, he became convinced that the Warren Commission, which investigated the assassination, was a farce and that the CIA had participated in a plot to kill Kennedy. Onstage, Mr. Sahl read excerpts from the commission report that he considered full of comically tortured logic, and he rambled on about various conspiracies.

He journeyed to Louisiana, where the controversial New Orleans district attorney Jim Garrison deputized him to help investigate an alleged government coverup. Putting comedy aside, Mr. Sahl spent several years traveling the country interviewing witnesses and evaluating evidence.

Invitations to appear on TV shows and in clubs dried up. In his 1976 memoir, “Heartland,” Mr. Sahl wrote that his earnings fell from $1 million a year to “about nothing.” But he made a comeback after Watergate, when his searing skepticism and dark view of American leadership better matched the national mood.

“The harvest of what we found came out repeatedly afterward in Watergate, the Iran-contra affair, the whole idea of shadow government and of people who think they know better what’s good for Americans,” Mr. Sahl told the makers of a public television documentary about him in 1989.

He returned to nightclubs and had a one-man Broadway show in 1987. Mr. Sahl still impressed with his steady supply of zingers.

One of them involved his friend, former secretary of state Alexander Haig, and the U.S. embargo of Cuba. Mr. Sahl explained: “I was with him when he lit up a Havana cigar, and I asked him, ‘Isn’t that trading with the enemy?’ He told me, ‘I prefer to think of it as burning their crops to the ground.’ ”

Morton Lyon Sahl was born in Montreal to American parents on May 11, 1927. His father, Harry, a failed left-wing playwright from New York, ran a tobacco shop to support his family. The Sahls later settled in Los Angeles, and the elder Sahl became an FBI clerk.

According to Nachman, Harry Sahl cast a pall over his son’s view of the world. “It’s all fixed,” he would tell Mort, referring to show business. “They don’t want anything good.”

In high school, Mr. Sahl joined the ROTC, and by his own account became an expert marksman and “something of a martinet.” At 15, he enlisted in the Army by lying about his age. His mother found him two weeks later and ushered him home.

Undaunted, he joined the U.S. Army Air Forces after high school graduation and was sent to an outpost in Anchorage, where his contrarian spirit made an untimely emergence. He grew a beard and tried to turn a base newspaper, which he edited, into a muckraking journal. His efforts earned him ample KP duty before his discharge in 1947.

He graduated in 1950 from the University of Southern California. While doing odd jobs, he wrote a novel and a play that found no takers.

He followed a girlfriend to San Francisco, where in 1953 he began trying out comic material at a basement bar called the hungry i, a rendezvous for beatniks that charged a 25-cent entrance fee.

Mr. Sahl, who had been living in the back of a station wagon, said it took three months to get his first laugh. The winner was a Cold War joke about McCarthy’s anti-communist crusades: “Every time the Russians throw an American in jail, we put an American in jail to show them they can’t get away with it.”

His success at the hungry i led to more prominent engagements in Los Angeles, New York, Chicago, Las Vegas and Miami Beach. A heavy coffee drinker largely averse to alcohol and cigarettes, he led a busy life that took a toll on his private affairs.

All three of Mr. Sahl’s marriages — to Sue Babior, former Playboy centerfold China Lee and Kenslea Ann Motter — ended in divorce. His son with Lee, Mort Sahl Jr., died of a drug overdose in 1996. He had no immediate survivors.

Mr. Sahl performed well into his 80s, even after a mild stroke. He often made light of death, but with a sharp political eye. Referring to the Windy City’s reputation for electoral fraud, he once quipped: “I’ve arranged with my executor to be buried in Chicago. When I die, I want to still remain politically active.”