The Playboy publisher was 60 at the time and was dating a 22-year-old named Carrie Leigh.
He's liberal, a big proponent of the First Amendment and not a big sports fan.
The Playboy founder had everyone from James Brown to Fleetwood Mac on his variety show and has been name-checked in countless hip-hop tracks.
Hefner's magazine was a platform for African-American leaders, including Martin Luther King Jr., during the 1960s civil rights struggle.
The Playboy founder saw himself as a campaigner for progressive causes, including sexual liberation.
In a 2004 interview with Howard Stern, Trump also suggested contestants were picked for their physical appearance.
Authorities detained seven people, including American Lauryn Elaine.
"The current administration sells half-truths and lies like they're day-old cookies at a bake sale."
Three movies cemented Harrison Ford's fame beyond his sci-fi heroes.
Aiming for a younger audience, the newly redesigned magazine features an Instagram-famous woman in a Snapchat-style photo on its cover.
The move represents the triumph of mainstream porn and not a victory for women.