Around the same time, Hentoff began freelance writing for "Esquire", "Playboy," "Harper's", "New York Herald Tribune," "Commonweal", and "The Reporter". From 1958 to 2009, he wrote weekly columns on education, civil liberties, politics, and capital punishment for "The Village Voice". He also wrote for "The New Yorker" (1960–1986), "The Washington Post" (1984–2000), and "The Washington Times". He worked with the Jazz Foundation of America to help American jazz and blues musicians in need. He wrote many articles for "The Wall Street Journal" and "The Village Voice" to draw attention to the plight of America's pioneering jazz and blues musicians.