The late magazine mogul's girlfriend for seven years—a majority of them as the "#1 girlfriend"—Madison was a prominent fixture in Hefner's life for nearly a decade. Having frequently visited the mansion while a 20-year-old college student in Los Angeles, the aspiring actress decided to move into the house a year later in 2001. The Oregon native, who was familiar with Playboy and had been a fan, soon became Hefner's lead girlfriend and the two appeared to fall in love.
Over the course of their seven years together, their untraditional relationship was chronicled on E!'s series, The Girls Next Door, with Madison the ever doting and loyal wife figure alongside co-stars and fellow girlfriends Kendra Wilkinson and Bridget Marquardt.
While the magnate expected to spend the rest of his life with her, a point of contention popped up between them when Madison expressed desire to marry the late star and start a family. Ultimately, Hefner's refusal to wed for the third time and his inability to procreate was considered their breaking point and she called it quits in 2008.
"Holly wanted very much to get married and have children and that wasn't in the cards for us," Hefner explained in a video for Playboy at the time. "I made a noble effort on the children's part of it. I was not prepared at this point to marry again."
Elayne Lodge/Playboy Enterprises
However, he eventually did. Following his breakup with Madison, he began dating twins Kristina and Karissa Shannonand, later, additionally Crystal Harris. In December 2010, he popped the question to Harris.
"I'm very surprised," Holly told E! News at the time of the engagement. "I have a lot of different feelings on it. I don't just feel one way. I kind of didn't want to put a generic statement out there like 'Congratulations!' because I felt everyone would see through that."
The eternal bachelor didn't have a smooth trip down the aisle. While his Playboy Playmate bride unexpectedly broke off their engagement five days before their vows, the two ultimately tied the knot in December 2012.
Michael Tweed/ZUMA Press
Madison had her own happily ever after when she said "I do" to longtime beau Pasquale Rotella a year later. However, two years into her married life as a mother and four years without any contact with Hefner, the former Playboy Mansion resident shed new light on her former life when she published her memoir, Down the Rabbit Hole. In the no holds barred book, the former Playboy cover girl and Hefner's one-time leading lady shared her own controversial account of her time at the famous property.
In print, Madison, who initially was under the impression the women did not actually have sex with Hefner, recalled her first night with him in formerly unheard vivid detail. "Two huge television screens projecting graphic porn lit up the otherwise dark bed," she wrote. "In the middle, a very pale man was tending to his own business (if you're catching my thinly veiled innuendo) and puffing on a joint before passing it around to the nearest blonde. The girlfriends, in various stages of undress, were sitting in a semicircle at the edge of the bed — some kneeling, some standing, some lying down."
Charley Gallay/Getty Images for Playboy
She claimed he offered her a Quaalude, alleged the orgy-esque activity would take place twice a week, that he disapproved of her short haircut and called her "old hard and cheap" when she wore red lipstick. According to Madison, the women at the mansion were also expected to abide by a curfew and that Hef fostered competition among the women.
"I tricked myself into thinking I had feelings for Hef," she wrote in the book. "He had this gentlemanly veneer, he was intelligent, and I loved watching old movies with him. I focused on the positive things, not the negative."
However, after suffering depression, suicidal thoughts and—according to Madison—Hef's accusations of infidelity, the two broke up.
"Over the course of my life I've had more than my fair share of romantic relationships with wonderful women. Many moved on to live happy, healthy and productive lives, and I'm pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight," he told E! News in a statement. "I guess, as the old saying goes: You can't win 'em all!"
While the two had their differing accounts of how their relationship played out, Madison wanted the public to know that her life has only gotten better.
"For so many years, I just wanted to move forward with positivity, only say nice things. I wanted to stand on my own two feet, start from scratch, just be me, not talk about Hef," she told E!'s Ken Baker. "But, I would get so many people coming up to me saying, 'Don't you miss the mansion?' or 'I'm sorry Hef didn't marry you' and I'd see everything that was written about me and people think they know me just because the know one side of me from the TV show, which was seven years ago…and I just didn't think overall it was a very good message for women because the best part of my life has been the seven years since I've left the mansion."