For Playboy mogul Hugh Hefner, mixing business and pleasure was a way of life. The publishing icon, who died yesterday at 91, left an indelible mark on American society with the magazine he founded in 1953 and the glamorous, sexy culture that flowed from it. He also lived up to the name of his empire, thanks to many relationships with lovely ladies who posed. As we look back on the life of the man who will be buried next to his first cover model, Marilyn Monroe, let’s take a minute to remember some of Hef’s hottest hook-ups.
Barbi Benton: Benton and Hef dated for a number of years and lived in the mansion between 1969 and 1976. The two have remained close friends.
Marilyn Cole: Hef never officially dated Cole, but he admitted to being “involved” with her around the time she appeared as Playmate of the Month in January 1972. She was the first full-frontal nude centerfold in the magazine and also came to the attention of singer Bryan Ferry upon being named Playmate of the Year in 1973. Ferry asked her to appear on the cover of the 1973 Roxy Music album Stranded, above.
Donna Michelle: The December 1963 Playmate of the Month and 1964 Playmate of the Year spent some intimate time with Hef during her Playboy tenure.
Kimberley Conrad: Conrad got hitched to Hef in 1989. They had two children together before officially divorcing in 2010.
Brande Roderick: The Baywatch actress was Playmate of the year in 2001, around which time she and Hef hooked up briefly.
Bridget Marquardt: Marquardt dated Hef at the same time as fellow The Girls Next Door stars Holly Madison and Kendra Wilkinson, though she never made it to the coveted spot of “#1 Girl.”
Holly Madison: One of Hef's few non-Playmate girlfriends, Madison became his “#1 Girl” in 2001, later appearing on The Girls Next Door. The two broke up in 2008, which Holly later said in her memoir was because she realized he had someone spy on her during a work-related trip to Las Vegas. After Hefner called her during her trip, saying she had given him “the worst night of [his] life” because she brought back to her hotel room later boyfriend, Criss Angel, she decided to pull the plug.
Kendra Wilkinson: Wilkinson became one of Hef's girlfriends in 2004 after he spotted her modeling at a Playboy Mansion party. They split after she met her husband, former NFL wide receiver Hank Baskett.
The Shannon Twins: After Hef's three The Girls Next Door girlfriends all left, he was quick to recover and soon invited identical twins Kristina and Karissa Shannon to move in with him.
Crystal Harris: Around the time he started dating the twins, Hef also began shacking up with Harris, to whom he proposed in December 2010. She accepted but called off the wedding five days out. They got back together in June 2012 and ended up getting married.