Holly Madison is a beautiful Playboy bunny who may be best known for being one of Hugh Hefner‘s privileged “house guests.” Madison has made quite the leap in her career. When you go from being just a pretty face with a gorgeous body to becoming somewhat of a name-brand, you’ve made quite the progress during your career. And, of course, a lot of her success she owes to the man himself, Hugh Hefner. Holly Madison didn’t start as the Playboy bunny she became. She started as a girl from a small town and evolved into a name that everyone all around the world knows.
Her road to success is one that many know well. It’s about a small town girl who wanted to hit it big in Hollywood. And Holly Madison knew the road to success wasn’t paved with personality. She had a few cosmetic surgeries that led to an increase in attention, and she knew exactly what to do when opportunity came knocking at her door. Because Hef chose her as part of his “special” group, she was thrust into the limelight. And Madison definitely took advantage. The headlines were big as Madison and other women were labeled as Hefner’s live-in “girlfriends.” A television show was made about their exploits that further sensationalized the experience. Memoirs written years later attacked some of the perceptions that were left behind by the television show and rumors. But the experience has led to a very successful career and life for Holly Madison, who has made the most of everything.
15. The Beginning
Holly Madison was born in Astoria, Oregon on December 23, 1979. Her name was actually Holly Cullen at the time of her birth, and little did she know where her life would head. Holly’s time in Oregon would be short-lived as her family moved to Craig, Alaska, located on Prince of Wales Island. Madison wasn’t born with an hourglass figure. She was actually a skinny blonde girl with a bit of a nose. She would never truly develop into the curvaceous beauty she would become. Instead, surgery would be the direction she would go… but that’s for later on. For now, Madison, a scrawny blonde girl from Oregon, headed north — way north. But it wouldn’t be long until Madison and her family would return back to Oregon, this time residing in St. Helens.
14. Finding Her Way
Madison was about to enter middle school when her family returned to St. Helens. Madison remained in her birth state all the way through college, attending Portland State University. Madison majored in both theater and psychology but wanted to get closer to the lights of Hollywood. So, she transferred to the campus of Loyola Marymount University, a campus nestled in the Westside of Los Angeles, California. Madison grew into an attractive young woman. But she wanted more and was determined to find a way to get it. With her good looks, Madison wanted to focus more on her career than her degree.
13. Heading to Los Angeles
Holly Madison was short on cash and needed to work to help pay for her time in college. Madison was skinny and pretty and went to hot-girl heaven aka Hooters. In addition to her time swinging wings and beers while wearing disappearing shorts and the tightest of tank tops, Madison started to compete as a model. She entered some Hawaiian Tropic modeling contests in hopes of making more cash and getting a little extra recognition. Madison recalls that she was curvy in some places, just not her boobs yet. She wanted to “balance” her body out and become a sexier version of herself. All of the time she spent as a Hawaiian Tropic girl and the visits to the Playboy Mansion were about to pay off.
12. Modeling and Hooters Pay Off
Due to Madison’s exposure modeling for the Hawaiian Tropic contests, she received a very fortunate invite to a Playboy Mansion party. This encounter was about to change her life forever. Madison, 21 years old at this point, was invited again, and again, and again. Madison used these parties to flirt and to enjoy all that the Mansion had to offer. That included the man himself, Hugh Hefner. After attending the parties for nearly a full year, Hefner was smitten with Madison and decided to invite her to move in. Right after moving in, Madison wanted to compete with some of the other curvy hotties in town. So, she begged Hefner for a gift: a new set of boobs. Naturally, the old man agreed, and she got her large breasts courtesy of Hef.
11. The Mansion
One of the most interesting things about Holly Madison’s ascent inside the hallowed walls of the Playboy Mansion was that she wasn’t a Playmate. So many of Hef’s “girls” became or were Playmates during their affairs with the old man. The year was 2001, and Madison had gone from struggling model and Hooters girl to enjoying the Mansion and the amenities that come with being part of Hef’s harem. But her time at the Mansion is a contradiction of memories that she, herself, questions. Although Madison would eventually share the Playboy cover with some of the other “girlfriends” she shared Hefner with, she was never classic Playmate material (until she had some surgeries, that is). But Madison’s time inside the Mansion is a tale of two stories, both told by Madison herself.
10. Fiction vs Reality
Before we talk about the fun, let’s dive into the scandal. Years after her time at the Mansion, Madison reflected in a 2015 memoir entitled Down The Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny. Now, there’s also a visual record of Madison’s time at the Mansion through another medium, the hit television show The Girls Next Door. The television series, starting in 2005 and filming for 5 successful years on E, featured Madison and fellow-Hefner house guest, blonde hottie Kendra Wilkinson. The show and Madison’s own words while she lived in the Mansion (and just after) don’t match up with her memoir. There’s quite a bit to unwrap with all of this.
9. Holly Wants a Ring on it!
Madison’s thoughts while she was in the Mansion seemed to point to a woman trying to “get a ring on it.” She was quoted as wanting to marry Hefner and have kids with him. Other women in the Mansion accused Madison of being “obsessed” with Hefner. She clearly loved the life the old man provided and wanted her sugar daddy to come through. But Hefner told Madison that he couldn’t see himself getting married again. He cited past failures and was clearly too smart at this point to get taken to the cleaners by another hot piece of a$$. Hefner saw Madison for what she was. Deep down, no matter how much Madison attempted to bend over backward (PUN INTENDED!!!) for Hefner, she couldn’t get him to spring for the ring. But the memoirs of both Madison and Wilkinson shed more light.
8. S-x With Hef
When it comes to sex in the Mansion, nearly everyone can confirm that a lot of late night activities have been going on for a long time. But concerning Hef and his in-house whores — oh, we mean “girlfriends” — Wilkinson had some pretty choice opinions on the matter. Basically, Hefner was a king and the ladies of the home didn’t want the sole burden to be on them all the time, so they would drag the newest, bright-eyed bunnies over in hopes of increasing the field, so to speak. The more girls in the room, the less likely the in-house ladies would have to put out. The “vets” forced the new hopefuls into their “rite of passage,” a few pride-swallowing minutes with the old man, although many of the other women have been quoted as stating that Madison was willing to do whatever Hefner wanted, whenever he wanted. That was, until she remembered everything differently while writing a memoir.
7. The Girls Next Door
The television series The Girls Next Door was a brilliant move by many. First off, it gave us a bird’s-eye view of what was going on inside the Playboy Mansion, which featured many hot girls having a great time, as if this were some sorority house gone bad. But the reality of what was going on versus what was shown on television may not have been a perfect mirror image. We’ll get to that. But the show featured both Kendra Wilkinson and Holly Madison as the stars of the show, as they were Hef’s girlfriends. The flaunting of this old man having beautiful, young, blonde, busty women falling all over his home and giving him attention may just be somewhat of a cliché. It was clear from the start that these women enjoyed being taken care of and loved the Playboy Mansion lifestyle afforded to them by Hefner. It was a “pay for play” scenario. And everyone made out nicely when the television series was a hit. It started in 2005 and would last for 5 successful seasons until the girls were out of Hef’s Mansion and out on their own.
6. Monday Morning Quarterback
First off, the moment these women tasted any kind of success and were able to parlay their own deals, they bounced on Hugh Hefner and the Playboy Mansion. This should come as little surprise as it was obvious from the start what their intentions were. And although Holly Madison played the role of longing girlfriend wanting to get married perfectly on the television series, the complete opposite came out after the fact. Madison brought about allegations of sexual misconduct and drug abuse in the Playboy Mansion and completely backed off of the notion that she was a little star-crazed puppy wanting Hef’s babies. But the reality was, when Madison was a nobody working at Hooters, she was more than willing to lay down for the opportunity to get into Hefner’s Mansion (aka bed). She played her part perfectly until she gained success and notoriety; then, she was able to stand on her own two feet and burned down the Mansion in her best-selling memoir. The things they do for money…
5. The End of the Mansion
Holly Madison moved on from life in the Mansion in 2008, but the television series limped forward for two more uneventful years. The girls who once roamed the Playboy Mansion were not nearly as interesting away from Hef’s eerie grasp, and the show quickly lost viewership and interest. As for Madison and Hefner? Well, Hugh Hefner described the end of their relationship in the most honest way possible: “If Holly says it’s over, I guess it’s over.” Yeah, sounds like he was crushed by the news. Clearly, there was a disconnect between Madison’s desire to get impregnated and married to the Playboy mogul and the reality of Hef knowing she was simply after his money and lifestyle. Madison landed on her feet, so to speak, with a gig on Dancing with the Stars. It was clear that Madison’s next avenue was the reality-television world she was already thriving in.
4. Las Vegas
As Madison’s time on The Girls Next Door grew to a close, she morphed into a reality-television regular. She caught on with a variety of opportunities, attempting to parlay her name recognition into any and all career avenues available to her. The year was 2009, and Madison planted a flag in Las Vegas, Nevada. Sin City would be Madison’s playground for the next three years. She caught everyone’s eye when she teamed up with Las Vegas Mayor Oscar Goodman and broke the Guinness World Record for the largest bikini parade. There were 281 parade participants, breaking the old record of 250. Aside from this sideshow, Madison dropped anchor at the Planet Hollywood Hotel, starring in her own Burlesque Peep Show. At the same time, she naturally signed on to do a reality television series entitled Holly’s World, which captured all of the exciting happenings surrounding the wannabe reality-television star.
3. Life Beyond Hugh
Despite Madison initially claiming to be destroyed by her breakup with Hugh Hefner (then, later on, rescinding such statements and proclaiming she was forced to do unspeakable acts with saggy wrinkly objects), Madison was able to move on and have a romantic life beyond the Playboy Mansion. In 2011, as Madison was on the tail end of her time in Las Vegas, she started dating Pasquale Rotella. In August of 2012, she announced that they were going to be expecting a baby together. Aurora Rotella was born on March 5th, 2013, and later that year, Rotella and Madison married at Disneyland. They have since gone on to have a second child together and remain in Las Vegas together, where their love initially blossomed. On a side note, Madison had her breasts insured for $1 million. You know, just in case.
2. The Memoir
Now, we come full-circle, returning to the juicy behind-the-scenes happenings of the Playboy Mansion. Remember, Madison was “broken” over her breakup with Hefner. She even was quoted as saying that she didn’t need men in her life and may not want to date for a long while due to the end of her fun with Hefner. Ah, how times change when you date a handsome man your own age. Her recounting of her time at the Mansion was scandalous. She lit fires everywhere, accusing Hefner of being a dirty old man and peddling drugs around the Mansion. Madison called the Mansion a “house of horrors.” Meanwhile, Playmates who lived there claimed the complete opposite. They claimed that Madison did kinky sex acts with Hefner others would not. And other claims include Madison dressing like Hefner and having an obsession with the old man. Also, other women recalled watching as Madison did the sexually degrading acts that she claimed she later regretted despite being a willing participant at the time. Hefner, for his part, has taken the high road, only stating that he enjoyed his time with Madison as he has with his many other girlfriends. Just gotta love that guy.
1. The Future
Well, it seems as though Holly Madison has milked all the juice out of her reality-television nuts. There’s very little left for her, but we’re certain she’ll make a few cameos in the reality-television world. When someone is desperate for a name who won’t cost an arm and a leg, they’ll give her a call. And we can see her hosting parades on television or being a New-Year’s-Eve person. Look, Madison is easy to look at. But remember, she went from an A to a D cup size. She had a nose job and tried to turn herself into something she perceived as beautiful and sexy. She parlayed that into an interesting relationship with Hugh Hefner, to say the least. She now has a family, a husband along with two children. She also has some name recognition and will pop up here and there. Just don’t count on seeing her on the cover of Playboy anytime soon.
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