The world lost a pop culture icon when Hugh Hefner, the iconic founder of Playboy, died on Wednesday, September 27. The legendary magazine publisher was 91, and left behind quite a legacy.

He was born Hugh Marston Hefner on April 9, 1926, in Chicago, and was the oldest of two boys born to Grace and Glenn Hefner. The publisher graduated high school in 1944 and founded Playboy in 1953, which he turned it into a world-renowned brand and empire. The businessman is survived by his wife, Crystal Harris, sons Cooper, 26, Marston, 27, and David, 62, and daughter Christie, 64.

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Scroll down to take a look back at Hugh Hefner’s iconic life and career in photos.