Holly Madison Biography

Also known as Holly Cullen

Born: on December 23, 1979 in Astoria, Oregon

Job Titles: Model

While most Playboy bunnies enjoyed their 15 minutes of fame before vanishing into obscurity, Holly Madison made long strides toward becoming one of the best known faces in the magazine’s history. As one-third of “The Girls Next Door” (E, 2005-09), a reality show centered on Hugh Hefner’s trio of buxom blonde girlfriends, Madison was the Playboy magazine founder’s main squeeze and the Mansion’s leading lady. Not taking her fame lightly, Madison also became Playboy ’s photo editor, co-authored a book with Hefner’s other girlfriends Bridget Marquardt and Kendra Wilkinson, and acted in films such as “House Bunny” (2008) and “Scary Movie 4” (2006). After her relationship with Hefner ended in 2008, Madison went on to compete in season eight of “Dancing With the Stars” (ABC, 2005- ), where she showed everyone that she could survive – and have a career – outside of the Playboy Mansion walls. Born on Dec. 23, 1979 in Astoria, OR, Holly Cullen moved to Prince of Wales Island in Alaska shortly after her birth. Her father, who worked in the timber industry, moved the family again when she was 11 years old to St. Helens, OR. It was there that Madison developed a love for performing, attending Portland State University to study theater and psychology. Two years later, she found her calling in the bright lights of Hollywood and began to pursue her dreams.

Madison transferred to Loyola Marymount University in Los Angeles to finish her collegiate studies. In order to afford tuition and the city’s high cost of living, the Oregon native worked at popular restaurant Hooters and competed in a Hawaiian Tropic model search. Modeling introduced Madison to Hugh Hefner, whom she had met at one of the lavish parties thrown at his Holmby Hills estate, the infamous Playboy Mansion. She continued receiving invites to his soirees until a year later when Hefner, who was 53 years her senior, asked Madison to become one of his seven girlfriends.

Becoming the Playboy magnate’s girlfriend also meant that Madison would live in the Playboy Mansion. In August 2001, the former model stepped inside the opulent and historic house that has been featured in everything from “Beverly Hills Cop II” (1987) to “Sex and the City” (HBO, 1998-2004), knowing her life was about to change. Eventually, the number of Hefner’s girlfriends whittled down and by February 2002, Madison was the Hef’s No. 1 girl. She even had the privilege of sleeping in his bedroom while the other two girlfriends, Marquardt and Wilkinson, slept in their own bedrooms down the hall. When she was asked what she thought about the special arrangement of their relationship, Madison responded, “I devoted 100 percent of myself to Hef the whole time we were together.”

The unusual yet interesting life inside the Mansion was the subject of the reality series “The Girls Next Door.” Madison, Marquardt and Wilkinson were the stars of the show, with Hefner popping up in each episode, often wearing his signature robe and slippers. The three girlfriends each had their own personalities that brought a humorous and sometimes touching slant to the show. While Marquardt was the bubbly one and Wilkinson was the rebel, it was Madison who proved the most ambitious of the trio. She headed up organizing parties at the mansion, planning all their trips and activities, and acting as a housemother to a revolving door of Playmates.

“The Girls Next Door” was a success its entire run. Because of this visibility, Madison was able to use her fame and being Hef’s main squeeze to her advantage. She showed interest in the magazine and became Playmate photo editor for several years, where she was able to pick Playmate candidates, direct shoots, and assist in designing pictorials. The show also made her, Marquardt and Wilkinson into stars, with all three appearing on “Larry King Live” (CNN, 1985- ), “The Today Show” (NBC, 1952- ), and “The Ellen DeGeneres Show” (NBC, 2003- ), among others.

Madison and the girls were also offered minor acting roles in film and television, especially when the Playboy Mansion was used in the storyline. She appeared as herself in the comedies “The House Bunny” and “Scary Movie 4,” as well as in the shows “Entourage” (HBO, 2004- ), “Curb Your Enthusiasm” (2000- ), “General Hospital” (ABC, 1963- ), and “The Apprentice” (NBC, 2004- ). The trio also appeared together on the cover of Playboy magazine three times, and co-authored the book The Girls Next Door in 2008. Yet while her professional star was on the rise, life inside the mansion was a different story. There were rumors that Madison and the other girlfriends constantly fought for Hefner’s affection and media attention. The topic of raising a family with her much older partner was also on every journalist’s mind. Madison later replied that she and Hef tried to get pregnant through in vitro fertilization, but to no avail.

The stress of making her relationship work in front of millions of viewers and wanting a family eventually took its toll on Madison. In 2008, she ended her relationship with Hefner, who coincidentally, also ended his relationships with Marquardt and Wilkinson. Viewers were caught by surprise with the breakup news, as episodes of “The Girls Next Door” continued to air, showing the group happy and content. Madison later explained it was her decision to publicly announce the breakup. “There were a lot of people - not just Hef - who wanted me to pretend we were still together for the sake of the show,” she said. “I tried to do that for a few weeks, but I couldn’t live like that.” By October of that year, Madison had moved out of the mansion. Marquardt and Wilkinson did the same. Paparazzi followed Madison and Hef’s other ex-girlfriends closely, curious to know what their next moves were going to be. A month after her breakup with Hef was announced, she was spotted with illusionist Criss Angel, who starred on the show “Criss Angel Mindfreak” (A&E, 2005- ). The pair dated for a few months. After their breakup, Madison proclaimed to People magazine that she was done with men and wanted to focus on her career instead.

In March 2009, the proper opportunity presented itself when country/pop singer Jewel dropped out of “Dancing with the Stars” competition due to knee problems. Producers brought in Madison, who admitted to not having had any dance experience, as her replacement. When the season premiered on March 9, 2009, Madison glowed on the dance floor, as she and dance partner Dmitry Chaplin performed the cha cha, earning 18 out of 30 points from the judges.

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