Model Crystal Harris was married to Hefner at the time of his death. The couple tied the knot in 2012 after meeting when she covered the December 2009 issue of Playboy. Harris was Hefner's third wife.
Kimberley Conrad is Hefner's second wife. The couple got married in 1989 before separating in 1998. They stayed married for their sons—Marston and Cooper Hefner—until 2010
Millie Williams was Hefner's first wife. The couple married in 1949 and divorced in 1959. They share two children together.
Marilyn Monroe was featured on the cover of the very first issue of Playboy in 1953. Selling around 50,000 copies, the issue catapulted the magazine and Hefner.
Hefner made Pamela Anderson a household name when he featured her on the October 1989 cover, and many people would go on to say that she was one of his favorite models of all time.
Hefner and Kendra Wilkinson shared a special bond as the model moved into the Playboy mansion at just 18 years old. They dated from 2004 to 2008.
Holly Madison was known as Hef's "main girlfriend" from 2001 to 2008. In fact, in 2008, the Playboy mogul stated he believed they would be together for the rest of his life.
Though they lost contact in recent years, Hefner dated Bridget Marquardt from 2002 to 2009. She also starred alongside Wilkinson and Madison on Girls Next Door.
Hugh Heffner dated Barbi Benton from 1969 to 1976 after the two met while co-hosting Playboy After Dark together. She would go on to appear on the cover of Playboy four times.