His son, Tom Hentoff, said his father died from natural causes at his Manhattan apartment.
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Schooled in the classics and the stories he heard from Duke Ellington and other jazz greats, Nat Hentoff enjoyed a diverse and iconoclastic career, basking in "the freedom to be infuriating on a myriad of subjects."
He was a bearded, scholarly figure, a kind of secular rabbi, as likely to write a column about fiddler Bob Wills as a dissection of the Patriot Act, to have his name appear in the liberal Village Voice as the far-right WorldNetDaily.com, where his column last appeared in August 2016.
Ellington, Charlie Parker, Malcolm X and I.F. Stone were among his friends and acquaintances. He wrote liner notes for records by Aretha Franklin, Max Roach and Ray Charles and was the first non-musician named a Jazz Master by the National Endowment of the Arts. He also received honors from the American Bar Association, the National Press Foundation, and, because of his opposition to abortion, the Human Life Foundation.
Hentoff's steadiest job was with the Voice, where he worked for 50 years and wrote a popular column. He wrote for years about jazz for DownBeat and had a music column for the Wall Street Journal. His more than 25 books included works on jazz and the First Amendment, the novels "Call the Keeper" and "Blues for Charles Darwin" and the memoirs "Boston Boy" and "Speaking Freely."
The documentary "The Pleasures of Being Out of Step: Notes on the Life of Nat Hentoff" was released in 2014.
Jazz was his first love, but Hentoff was an early admirer of Bob Dylan, first hearing the then-unknown singer at a Greenwich Village club in 1961 and getting on well enough with him to write liner notes two years later for Dylan's landmark second album, "The Freewheelin' Bob Dylan."
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"The irrepressible reality of Bob Dylan is a compound of spontaneity, candor, slicing wit and an uncommonly perceptive eye and ear for the way many of us constrict our capacity for living while a few of us don't," Hentoff wrote.
At a time when the media alternately treated Dylan like a prophet or the latest teen fad, Hentoff asked well-informed questions that were (usually) answered in kind by the cryptic star. Hentoff also was willing to be Dylan's partner in improvisation. A 1966 Playboy interview, he later revealed, had been made up from scratch after Dylan rejected the first conversation that was supposed to be published by the magazine.
As a columnist, Hentoff focused tirelessly on the Constitution and what he saw as a bipartisan mission to undermine it. He tallied the crimes of Richard Nixon and labeled President Clinton's anti-terrorism legislation "an all-out assault on the Bill of Rights." He even parted from other First Amendment advocates, quitting the American Civil Liberties Union because of the ACLU's support for speech codes in schools and workplaces.
Left-wing enough to merit an FBI file, an activist from age 15 when he organized a union at a Boston candy chain, Hentoff was deeply opposed to abortion, angering many of his colleagues at the Village Voice and elsewhere. In 2008, he turned against the campaign of Barack Obama over what he regarded as the candidate's extreme views, including rejection of legislation that would have banned partial birth abortions.
Hentoff was born in 1925, the son of a Russian-Jewish haberdasher. Thrown out of Hebrew school, he flaunted his unbelief, even eating a salami sandwich in front of his house on Yom Kippur, the Jewish day of fasting and atonement. In 1982, his opposition to Israel's invasion of Lebanon led to a trio of rabbis declaring he had been excommunicated.
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"I only wished the three rabbis really had the authority to hold that court," Hentoff later wrote. "I would have told them about my life as a heretic, a tradition I keep precisely because I am a Jew."
He was educated as a boy at Boston's Latin School, alma mater to Ralph Waldo Emerson among others. But his best lessons were received at a local jazz joint, where Ben Webster and Rex Stewart were among those who took a liking to the teenage fan and became, Hentoff recalled, "my itinerant foster fathers." Back in the classroom, Hentoff would hide jazz magazines inside his textbooks.
In college, Northeastern University, Hentoff found a home at the Savoy Cafe and befriended Ellington, drummer Jo Jones and others. Ellington not only lectured him on music, but enlightened young Hentoff (who eventually married three times) on the loopholes in monogamy. "Nobody likes to be owned," Ellington told him.
After graduating, Hentoff worked as a disc jockey and moved to New York to edit DownBeat, from which he was fired in 1957, because, he alleged, he had attempted to employ an African-American writer. A year later, he joined the Village Voice and remained until he was laid off in December 2008.
"I came here in 1958 because I wanted a place where I could write freely on anything I cared about," Hentoff wrote in his final Voice column, published in January 2009. "Over the years, my advice to new and aspiring reporters is to remember what Tom Wicker, a first-class professional spelunker, then at The New York Times, said in a tribute to Izzy Stone: 'He never lost his sense of rage.' Neither have I."