William F. Buckley Jr. And Hugh Hefner, 1966
Andrew Sullivan links to a Roger Ebert article about Hugh Hefner, and includes one clip of Hefner’s appearance in 1966 on Firing Line with William F. Buckley Jr.
The whole interview — which covers everything from what Hefner referred to back then as “the Playboy philosophy” to nuclear weapons — is worth watching (total viewing time is about an hour):