David L. Lewis's straightforward documentary The Pleasures of Being Out of Step explores two sides of Nat Hentoff's very long seven-decade career as a jazz critic and social commentator. As a jazz critic, he is rightly regarded as one of the best of the best. As a social commentator, however, his record is not as impressive.
Those who are interviewed about his influence on jazz culture and history—Stanley Crouch, the late Amiri Baraka, and others—have nothing but praise to offer. Unlike other white jazz critics of his time/prime (1952 to 1969), Hentoff took black artists seriously, he wrote liner notes that displayed his deep respect for their creative intelligence, and he developed close friendships with revolutionary black musicians like Charles Mingus and Max Roach. On top of that, he founded a highbrow jazz journal, The Jazz Review, and ran the legendary label Candid. When it came to music, Hentoff was flawless.
Those who are interviewed about his contributions to American social commentary, on the other hand, are rightly unimpressed. Hentoff turns out to be a crank whose faith in the Bill of Rights is incredibly naive. He also was wrong on AIDS, which he wrote about in the 1980s, and despite being a progressive in matters concerning black Americans, he was right-wing when it came to women (he is pro-life). Hentoff is a libertarian, a political view that comes naturally to those who put complete faith in a document that was written by a bunch of wealthy white men 200 years ago. Hentoff is also an American original, a consequence of his faith in the music made by some of the most oppressed members of this society.