Conrad was an Alabama girl who was given the chance to take her modeling career to the next level in January 1988 when she debuted in the magazine.In '89, she was crowned Playmate of the Year, though the real prize was taking Hefner off the market.Marilyn Cole, Karen Christy and Lillian Mueller being some of the notable Playmates whose relationships with Hefner fall into that category.
Some of her interactions with then-host Donald Trump were seen as inappropriate by audiences, considering Trump was married to Melania.During that time she was featured on three covers as well as two spreads, one of which she went all the way for."I was shy and would make the photographer turn his back when I changed poses," she said."By the second one, I just let it all hang out." They remained an item for eight years and, according to the official website, Benton "coaxed him into parasailing, skiing and globe-trotting.Together they epitomized a swinging romance." Benton launched a short-lived career as a country singer in the '70s and was best known for the track "Brass Buckles." Hefner was still romantically involved with Benton when he met the captivating Lillian Müller.
Hef (as his many girlfriends would come to call him) re-branded himself as his man-about-town, and as his popularity grew, so too did his magazine.