Hugh Hefner's Girlfriends Then And Now

He lived his life like there was no tomorrow, and on Sept. 27, 2017, that turned out to be the case for Hugh Marston Hefner. The enigmatic founder of the Playboy empire passed away peacefully surrounded by loved ones, according to a statement (via People.) "My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights, and sexual freedom," said his son, Cooper.

Whether Hefner actually empowered or exploited women is a debate that was reignited in the wake of his death at the age of 91, but whatever your opinion of the man, his historic place in pop culture is indisputable. Hefner's journey to stardom began when he returned from military service during WWII to discover that his first wife, Mildred Williams, had allegedly cheated on him, which he later described as "the most devastating moment" in his life. Playboy was born out of that despair, and Hefner reborn with it.

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. His reputation as a ladies man preceded him, and the older he got, the more women he dated. Here's what some of those ladies look like today.

Barbara Lynn Klein intended to become a veterinarian but soon realized that was a non-starter because she "couldn't stand the sight of blood." She set her sights on the entertainment industry instead and signed with a commercials agency, but she didn't work in ads for long. In 1968, at age 18, Klein landed a role on the Playboy After Dark TV show working alongside Hefner himself. It didn't take long for Hef to make his move.

"I told him I never dated a man over 24," Klein said (via People). "He told me he never dated anyone older than that either." Hefner convinced her to change her name to Barbi Benton and move into the Playboy Mansion, where she lived for almost a decade. 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 Playboy 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. The Norwegian beauty was working in London when she was spotted by magazine scouts, and her rise within the organization was meteoric. She was featured as Miss August 1975 and named Playmate of the Year in 1976, bringing her into direct contact with Hefner. He reportedly couldn't resist her Scandinavian looks, which Müller thanked God for in an interview with Sarah Best. "God gave me good genes," she said. "I was born naturally good-looking."

Within a year of arriving in the United States, Müller moved into the mansion and experienced a whole new world. "There was a walk-in refrigerator full of food like I'd never seen before," she told Sarah Best. "Boiled eggs in trays, crab legs, buckets of peeled shrimp, whole grilled chickens, salmon, filet mignon... I used to pull up a chair and eat. Then I'd move onto desserts: German chocolate cake, apple pie, strawberry shortcake, cookies and ice cream." Unfortunately, Müller began to experience health issues; anaemia and low blood sugar reportedly contributed to anxiety and depression.

She recovered after seeking guidance from one of Hollywood's top holistic doctors and went on to star in music videos for Van Halen and Rod Stewart. Alas, she never achieved her dream of making it as an A-list actress. Nowadays, she's an outspoken advocate for healthy eating and healthy living.

Hefner tied the knot for the second time in 1989, shocking the world and everyone around him. "I can't believe he's doing it," friend James Caan said, according to People. "The man could shake Canada, and a thousand beautiful girls would come tumbling his way." 

In 1988, a matter of months before he became engaged, Hefner had said, "There is probably nobody in America who has made it more publicly clear for the past 25 years that I do not plan on getting married again," but that was right before he got to know Kimberley Conrad.

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. "Hef and I started dating, got married, had kids, and the rest is history," she said in a Playboy interview (via the Daily Mail). "There was a common misconception that I put the kibosh on the partying at the Mansion. It had nothing to do with me." 

The 54-year-old recreated one of her iconic '80s cover shoots in July 2017, just a few months before her ex-husband (they divorced in 2010 after years of separation) passed away.

Sandy and Mandy Bentley were the first set of twins that Hefner started dating simultaneously. They were two Catholic girls from Chicago who the mogul met briefly in Hollywood hot spot Garden of Eden and then decided to track down. 

"The night I met them, I said, 'You girls dropped from heaven,'" Hefner told Rolling Stone in 1999. "Then they had a drink with me. I got their first names but not their last names or phone numbers, and suddenly they were gone. It took me a month to find them." Find them he did. One was studying in Las Vegas; the other home in Chicago. As Hef tells it, all it took was a few phone calls, and the Bentley twins were getting ready for life at the mansion. "Mandy has just moved here, and Sandy's coming out as soon as her semester is over," he said.

The girls made cameo appearances in Sex and the City and Two and a Half Men during their 15 minutes of fame, but their relationship with Hefner started to break down the following year. According to CBS News, in the summer of '99, Sandy began seeing Wall Street multimillionaire Mark Yagalla, who reportedly showered her with waves of expensive jewelry. She was later ordered to return it all after Yagalla was exposed as a con artist, but before the handover, she and her new boyfriend, Michael Tardio, attempted to sell some of it. Tardio and a friend were shot dead by unknown assailants, and the jewelry was never recovered.

The Bentley twins weren't the only girls sharing Hefner's big round bed at the time. Believe it or not, Sandy and Mandy were joined by Brande, a Baywatch star who came into Hefner's life after appearing in the magazine in April 2000. There were no surprised faces in the mansion when Brande Roderick was named 2001's Playmate of the Year. ”We all love each other,” Roderick said of the Bentley twins, who wore matching bunny costumes to the magazine's Valentine's party, reported The New York Times. ”We're like a family.” 

That family came apart when Sandy decided to pursue love outside of Hef's harem, but Roderick stuck around longer, and her career post-bunny suit shone a bit brighter. She landed minor film appearances in The Nanny Diaries and the Starsky and Hutch reboot and guest-starred in a number of TV shows, including Joey and Beverly Hills, 90210. 

Roderick is probably best remembered for her time on The Celebrity Apprentice, but for all the wrong reasons. Some of her interactions with then-host Donald Trump were seen as inappropriate by audiences, considering Trump was married to Melania. According to a 2016 report in the Daily Beast, Trump openly discussed his desire to both sleep with and marry Roderick, but she denied that he was ever inappropriate via an Instagram post.

Hollywood native Tina Marie Jordan comes from a big family, growing up with two brothers and six sisters in what she described as a "Brady Bunch" set-up. The blonde bombshell burned though numerous jobs after completing her studies and was in the process of transitioning into real estate when she met Hefner at Garden of Eden, one of his regular haunts. "I went to college, business school, and cosmetology school," she told Playboy. "I tried many different jobs and just wasn't happy. I was a loan processor—boring!—for two years and met Hef when I was going to get my real estate license."

Jordan joined the ranks of Hefner's girlfriends and started calling the mansion home. Soon after, she was featured as Miss March 2002, and that same year, the magazine interviewed her about a relationship with its founder. "Hef just wants to have a good time and be happy," she said. "He's a warm and generous person, a family man who cares a great deal about me and my three-year-old daughter. My 16-year-old brother thinks I'm so cool now because he got to meet Fred Durst at Hef's birthday party." 

Hefner and Jordan remained close after they split, appearing in the odd episode of Hefner's The Girls Next Door TV show, but a solid career in television never materialized for her. Nowadays, she is perhaps best-known for her selfie-laden Instagram feed.

Bridget Marquardt was one of the stars of The Girls Next Door and one of Hefner's three girlfriend's at the time the show began. At 31, she was the oldest of his partners, and she reportedly began to worry about her future while filming the show. 

According to Us Weekly, Marquardt decided to freeze some of her eggs in hopes of making her dream of starting a family come true after leaving the mansion. She called it an "insurance policy" she hoped she wouldn't have to use. She moved out three years after shacking up with Hef when she fell for cinematographer Nicholas Carpenter. When the couple failed to conceive via IVF treatment, the pair utilized her frozen eggs as a last hope. "None of my eggs survived," she revealed on Australia's The Morning Show (via the Daily Mail). "It was devastating for me, all this time I thought I had an amazing insurance policy but it didn't work out." 

That painful interview took place just months before Hefner's death. Marquardt said she had not seen him in years. "He told me there was always an open door, but I heard that that's not quite true lately," she said.

Another star of The Girls Next Door, Holly Madison, was discovered by Hefner's scouts while working as a Hooters girl to cover the cost of her tuition fees. The Oregon-born beauty was studying theater at Loyola Marymount University in Los Angeles, and she apparently didn't need a second invitation once she knew Hef was interested. She visited the mansion, and a year later in 2001, she moved in just in time to land a spot on the E! reality series. The show made her famous, and by the time her seven-year relationship with Hefner came to an end in 2008, she had enough star power to front her own show.

Holly's World aired for two seasons between 2009 and 2011 and followed her attempts to establish herself in Las Vegas. Unfortunately for Madison, her show was one of the first to be axed when E! decided to rid itself of the "trashy" programming that had become associated with its name. 

However, that wasn't the end for the former cover girl. She just needed to switch mediums. In July 2015, Madison made The New York Times best-seller list with Down the Rabbit Hole. In the book, she revealed the reason she decided to leave Hefner: "I learned Hef was the manipulator and that he pitted us against one another," she wrote (via Us Weekly). "I realized I wasn't treated well...  I don't have any loyalty to Hef."

The last of the original Girls Next Door trio, Kendra Wilkinson, was paying the bills working as a dental assistant when a customer encouraged her to pursue modeling. Whether this was an attempt at a pick-up or simply some honest advice isn't clear, but what is clear is that Wilkinson took the comments to heart. She scored a gig as a Painted Lady at Hefner's 78th birthday bash, where she made quite the impression on the host. Within a matter of days, she was officially one of Hefner's girlfriends and had moved into the mansion to live with him, Madison, and Marquardt.

Five years later, Wilkinson moved out on good terms. She actually held her wedding with former pro football star Hank Baskett at the mansion in June 2009. She's been very open about her time with Hefner and company, even with her son. "It starts now with teaching [my family] who I am," she told E! News. "I have nothing to hide."

Twin sisters Kristina and Karissa Shannon caught the attention of TV audiences after making the finals of the 55th Anniversary Playmate Search. They lost the title to Ukrainian model Dasha Astafieva, but just getting there was enough to make an impression on Hefner. Smitten with the pair, he offered the girls a joint centerfold shoot and invited them to live at the mansion as new girlfriends, even reportedly giving them full use of his legendary circular bed to sweeten the deal. They accepted and quickly became a hit with audiences—their first appearance on The Girls Next Door was the most-watched season opener in the history of the show.

With media spotlight comes media scrutiny, and it wasn't long before the twins' past was being dredged up in the press. According to the New York Daily News, the sisters were put on probation following felony assault charges related to a fight at a house party. Their residency at Hefner's casa came to an end in 2010, and things haven't exactly been going great for them since. The pair was involved in a car accident that reportedly led to Kristina getting slapped with a DUI in 2015, and more recently, the ladies attracted negative attention connected to their weight gain.

When Crystal Harris attended a Halloween party at the mansion in 2008, she had no idea she would end up becoming the Hefner's third and final wife. "He was so easy to talk to," she told Playboy. "We were both psychology majors, so we had a lot in common. It was like we already knew each other." Hefner fell head over heels for Harris, and she quickly became his No. 1 girlfriend, appearing in his magazine as Miss December 2009. A year of wining and dining followed, before Hefner popped the question. She said yes, but nerves later got the better of her, and Harris called the whole thing off just days before the ceremony

"I was overwhelmed," she told the magazine. "There were legal proceedings—a prenuptial agreement, Playmate contracts—and there were other girls. It was too much for me." It took another year for Harris to decide to finally became Crystal Hefner, marrying the entertainment icon in a private ceremony in December 2012. 

Following his death, Harris spoke to Us Weekly. "I am heartbroken," she said. "He was an American hero. A pioneer. A kind and humble soul who opened up his life and home to the world. I felt how much he loved me. I loved him so much. I am so grateful." She added, "He gave me life. He gave me direction. He taught me kindness. I will feel eternally grateful to have been by his side, holding his hand, and telling him how much I love him. He changed my life, he saved my life. He made me feel loved every single day. He was a beacon to the world, a force unlike anything else."