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Hugh Hefner, the man who founded the famed, and infamous, Playboy magazine has died. He was 91. 

Hef died of natural causes at his home on Wednesday night (Sept. 28), per Playboy Enterprises.

What? Don’t act like Hip-Hop heads weren’t sneaking peaks at Playboy, too.

This is where we remind you he was in Nelly’s “Work It,” featuring Justin Timberlake, video (~4:30 mark).

Says the New York Times:

Hefner the man and Playboy the brand were inseparable. Both advertised themselves as emblems of the sexual revolution, an escape from American priggishness and wider social intolerance. Both were derided over the years — as vulgar, as adolescent, as exploitative, and finally as anachronistic. But Mr. Hefner was a stunning success from his emergence in the early 1950s. His timing was perfect.

He was compared to Jay Gatsby, Citizen Kane and Walt Disney, but Mr. Hefner was his own production. He repeatedly likened his life to a romantic movie; it starred an ageless sophisticate in silk pajamas and smoking jacket, hosting a never-ending party for famous and fascinating people.

The first issue of Playboy was published in 1953, when Mr. Hefner was 27 years old, a new father married to, by his account, the first woman he had slept with.

Rest in power Hugh Hefner.