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Hugh Hefner, the man who created a magazine empire, died Wednesday at the age of 91 and his legacy includes some of the most famous Playboy playmates ever to grace the cover.

Veuer's Nick Cardona (@nickcardona93) has that story.

In the '90s, Smith gained popularity with Playboy and was named the 1993 Playmate of the Year.This file photo shows Anna Nicole Smith holding her daughter, Dannielyn Hope, and Howard K.Stern during a interview with Entertainment Tonight celebrity television show at the couple's home in the Bahamas in October 2006.In 1994, at age 26, she controversially wed 89-year-old oil tycoon J. She went on to fight for a share of her late husband's billion-dollar estate.During her court fight, she was the star of her own reality show "The Anna Nicole Show" in 2002 to 2004.

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