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The original playboy has passed. Hugh Hefner, the founder of the iconic Playboy magazine, died at the Playboy Mansion, of natural causes at age 91, Playboy Enterprises said in a statement on Wednesday. Hefner started the legendary Magazine in Chicago in 1953 with the help of  a $1,000 loan from his mother. From there the publication went on to lead the “sexual revolution” in the 60’s and 70’s with its full frontal nudity in its speads.

The first centerfold or “Playmate of the Month,” an iconic feature of the monthly magazine, was Marilyn Monroe. Other notable celebs who posed for Playboy magazine include Drew Barrymore, Le Toya Jackson, Farrah Fawcett and more.

Playboy also help kick off the careers of Pamela Anderson, Anna Nicole Smith and more after posing nude in the magazine. Hefner also helped out fellow legend, the late Dick Gregory. Gregory was working at the black-owned Roberts Show Bar in Chicago when he was spotted by the Playboy founder, who was in the audience.

Hefner hired Gregory to work at his Chicago Playboy Club, a move the comic called brave and important during the 2001 Comedy Central roast of Hefner. It was also Hefner who gave Gregory the funds to help locate the bodies of three slain Civil Rights workers in Mississippi in 1964.

In 1994, Playboy hit the world wide web with Playboy Online. In 2016, Playboy announced  the end of full frontal nudity in its magazine.

The Hugh M. Hefner First Amendment Award was created by Christie Hefner “to honor individuals who have made significant contributions in the vital effort to protect and enhance First Amendment rights for Americans.”

Hefner was survived by his wife, Crystal, his sons, Cooper, David and Marston, and his daughter, Christie.

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