Holly Madison Biography

Holly Madison was born in Astoria, Oregon (home of The Goonies), but soon moved to the sparsely populated Prince of Wales Island in Alaska. Growing up she spent a lot of time playing in the woods, reading Nancy Drew mysteries and watching bears rummage through our garbage.

Wanting to give their kids “a more normal life,” her parents moved my family to Oregon when she was in middle school. When she looks back on her middle and high school days she said sees an Alaskan fish out of water. One that wasn’t good at socializing or fitting in, despite being involved in numerous school activities.

Of course, as Holly said, “I think everyone saw themselves as a nerd in high school, though, don’t you?” Wanting to be an actress like Marilyn Monroe or Jean Harlow, she chose to study theater and psychology at Portland State University in Portland, Oregon.

Frequent family trips to Disneyland led her to love Southern California and, after two years at PSU, she transferred to Loyola Marymount University in Los Angeles. To pay the bills, Holly found work as a Hawaiian Tropic model and as a roller skating waitress at Hooters in Santa Monica. According to Holly, the hotties at Hooters talked about the exciting parties they attended at the Playboy Mansion. After hearing the hype, she was naturally thrilled when one of Hef’s friends saw her in a Hawaiian Tropic contest and put me on the Mansion’s party list.

The Midsummer Night’s Dream party was her first Mansion experience. She attended with a few of her girlfriends from Hooters, explored the place, and saw lots of celebrities and Centerfolds. She was the most excited to meet Hef, Seth Green (from the Austin Powers movies) and Heather Kozar, one of Holly’s favorite Playmates. Feeling overwhelmed, she and the girlfriends left early that night, but not after feeding the squirrel monkeys that reside adjacent the mansion.

After about a year of coming to the Mansion parties, Holly finally got a chance to really talk to the elusive Mr. Hugh Hefner. She knew the two would have a lot in common, and as luck would have it, hit it off immediately. Hef then invited her on a date and that started the initial romance. 

Holly has reported that living at the Mansion is much fun. In addition to spending time with Hef, her favorite things about living there are getting to know all the Playmates and traveling in style with Hef and the girls. Believe it or not, her favorite place they have been together has been Disney World in Orlando. Holly has a goal to visit every Disney park around the world. So for her it’s two down, three to go!

Mansion life took an interesting turn for the better for both the girls and viewers. The Girls Next Door follows Holly and Hef’s two other girlfriends, Bridget and Kendra, on their not-so-ordinary daily adventures. Holly even said that sometimes it’s a pain in the butt to have cameras following her 24/7, but the show has led only to greater opportunities.

Contrary to what most people might expect, living at the Mansion has planted Holly’s feet more firmly on the ground. Leading the glamorous life day after day led her to shed her need to become the next Marilyn Monroe. She is currently studying real estate at UCLA Extension and business at Santa Monica College. Her goals are to finally get her degree, to continue living with Hef and her dogs, and to someday be a mom.