Crystal Harris
The 31-year-old model 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
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 when they finally filed for divorce.
Millie Williams
Williams was Hefner's first wife. The couple married in 1949 and divorced in 1959. They share two children together, his 64-year-old daughter, Christie Hefner, and his 62-year-old son, David Hefner.
Christie Hefner
The Playboy mogul's one and only daughter—whom he shared with his first wife, Millie—Christie worked for the company for 27 years and held the title of CEO for 21 years.
Marilyn Monroe
The blonde bombshell 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—who started it with a mere $8,000 loan—to success. In fact, he cared so much for Monroe, he will be buried beside her at the Westwood Village Memorial Park in Los Angeles, Calif.
Pamela Anderson
It's safe to say 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. In fact, she graced the final nude issue of Playboy—her 14th cover for the magazine—in 2016, before the company reinstated nudity earlier this year. Anderson couldn't control her tears upon hearing the news of his death, penning an emotional poem in his honor.
Kendra Wilkinson-Baskett
Hefner and the former Girls Next Door star shared a special bond as the model moved into the Playboy mansion at just 18 years old. They dated from 2004 to 2008. However, following their split, Wilkinson went on to marry Hank Baskett, and Hefner actually helped host the wedding at the mansion, sitting second row to support his ex-girlfriend's happy ending. "Hef changed my life," Wilkinson told E! News in a statement. "He made me the person I am today."
Holly Madison
Another star of Girls Next Door, 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. Unfortunately, he never thought that he would marry her, and they broke up shortly after. In 2015, Madison released her book Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, which criticized Hefner and the whole Playboy lifestyle.
Bridget Marquardt
Though they lost contact in recent years, Hefner dated Marquardt from 2002 to 2009. She also starred alongside Wilkinson and Madison on Girls Next Door.
Barbi Benton
Hef dated 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.
Mary O'Connor
O'Connor worked as Hefner's secretary and the "mansion mother" for over 40 years. When she passed away in 2013, he tweeted, "Mary passed away today. We loved her more than words can say."