Don't be another Wonder Woman or Pennywise this Halloween.
The Playboy publisher was 60 at the time and was dating a 22-year-old named Carrie Leigh.
The common phrase covers a wide array of possibilities.
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.
Hefner, 90, the founder of the Playboy empire, will still live in the mansion for the rest of his life.
Chloe Goins claims Cosby drugged and molested her at the Playboy Mansion when she was a minor. Hefner, she claims, suggested she have drinks with the comic.
Aiming for a younger audience, the newly redesigned magazine features an Instagram-famous woman in a Snapchat-style photo on its cover.