Hugh was a staunch supporter of the American Civil Rights movement, raging against segregation and celebrating black artists, musicians, performers, and activists. The very first Playboy interview was with Miles Davis, conducted by Alex Haley, a black journalist who later wrote the seminal novel, Roots. The magazine also went on to feature the likes of Muhammad Ali and Malcolm X, and published the last interview with Martin Luther King Jr. before his death.
In 1959, Hef organized the Playboy Jazz Festival in Chicago, donating ticket sales to the NAACP. When Playboy Clubs across the country became franchised, and Hugh learned that some owners refused to grant membership to African Americans, he literally bought them all back and straightened things out.