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His legacy lives on.

Iconic media figure Hugh Hefner passed away peacefully in his home on Wednesday at age 91. Over the course of his life and career, the late magazine mogul was known for his wild and lavish lifestyle, but there were definitely some moments that took the cake! 

He never shied away from his preference for younger ladies. In a 1985 interview with David Letterman, he was very upfront about his tastes. When Letterman asked if he would be interested in a woman 50 years of age, Hugh's response said it all. "Probably not romantically," he told the host. 

There is plenty more where that came from! Watch the video above for all of Hef's craziest moments! 

Don't miss E! News every weekday at 7 and 11 p.m.

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