Hugh Hefner, iconoclast
How we feel about the Playboy: it's complicated

Say what you will about Hugh Hefner, the controversial creator, publisher, and editor of Playboy magazine who passed away last week, but the man had good taste. He created and lived the playboy lifestyle (or what we think of now as the Mad Men lifestyle) that so many guys desired: a beautiful woman on his arm, a dry martini in his hand, and a pipe in his mouth. Not only did Hefner run the most popular magazine in the world, starting in 1959 he also aired the hip and “happening” variety/talk show, Playboy Penthouse which was shot in Chicago, in what appeared to be Hefner’s expansive penthouse apartment overlooking the Windy City (it was actually a studio built to look like his home). A few years later, after Hefner moved to L.A. and into the infamous mansion, he had a similar TV show called Playboy After Dark.
Every week, a different celebrity or two would arrive to the party hosted by Hef (as he was known), and co-hosted by the Playboy playmate of the month. In a large, very modern room filled with gorgeous women and elegant men, the hottest performers of the day would play a song or two, sit down for a chat with Hef, and cuddle with a playmate.
A renowned civil rights supporter, Hef hosted many African American performers on the show at a time in our history when that was not a popular decision to make. But week after week, people like Sammy Davis Jr, Marvin Gaye, James Brown, and Ike and Tina Turner arrived at Hef’s “doorstep” and entered into a fantasy world of glamour and equality. It was awesome.
Here, the cool jazz-loving playboy invited the Dave Brubeck Quartet to play their huge hit, “Take Five.”