Sometimes, I like to take a break from all the serious non-fiction books I read with something light. A while ago, I did just that by reading the book Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny by Holly Madison. The book happened to be just the refreshment I needed.
Non-fiction books often make me analyze every paragraph, take notes, and consider every thought. It requires brainpower. I occasionally want to relax and enjoy myself, and this book was an adventure into a fascinating, different world. The book is Holly’s memoir on how she went from smalltown girl to one of Hugh Heffner’s wives at the Playboy Mansion to leaving him and becoming a headliner in Las Vegas.
Before I get into my book summary, I want to start with my book review this time because I think it’s more important.
First, it’s a long read. It got a bit boring as it went on as she seemed to want to tell every little story. Fortunately, I listened in audiobook form, which helped.
I noticed other reviews thought the book was biased or seen through her own rose-colored glasses, but I thought it was fairly accurate based on her own story. In some cases, I believe she presents a more realistic perspective on who Hugh Hefner is than media or Hugh himself since they portray him as this playboy hero. Holly, at times, shows him as a manipulative, short-tempered old man who puts women against each other through jealousy and dangles career opportunities and money in exchange for a sexual harem lifestyle.
In fact, this revelation on the dynamic between Hugh and his women and Hugh’s personality was the most surprising part of the story. Seen through her eyes, he had a temper and ego. He loved to be recognized at nightclubs. He would flip out if one woman wore a lipstick color he didn’t like, but then delight when he saw a new girl wear it to get the others jealous, which worked. Part of this jealousy battles that Holly mentioned was probably due to just girl-guy ratio dynamics. Things are bound to turn ugly when dozens of women are living together and trying to win the favor of just one man.
I also discovered Hugh gave his official girlfriends a monthly stipend and housing in his mansions. The speed that women got things and the cost of things were another point of contention and comparison among women. I don’t think his manipulation was ethical or right, yet it worked. He had them wrapped around his finger … to a point. Many girlfriends broke up with him and moved on after a few years, despite his protests, usually after they got their centerfold or they got the bump in their education or career they wanted.
Holly and the other women didn’t like admitting to hooking up with Hugh since he was so old. She did mention his sexual parties did happened once a week, but she played it off quickly by saying she usually got other girls to partake so she didn’t have to.
There were two areas when I thought she may be painting a better picture of herself, and these made sense as to why. The first was when she claimed she did not sleep with Criss Angel when they hung out once when she was still Hugh’s girlfriend. And the second was after she broke up with Heff and claimed she went onto make millions as a headliner in Las Vegas with Criss. This breakup infuriated Heff and she was probably told that she would never make anything of herself, so it makes sense that she wanted to prove herself wrong. I doubt it’s that easy to make so much money, even in Vegas.
Since I’m scanning for life lessons, I did pick up a few surprisingly. From an evolutionary biology perspective, I marveled at this woman’s climb to career success through her relationship with successful men and career decisions. She started out young and beautiful but with no money or connections, got noticed by Hugh, worked her way up to be his main girlfriend, got a centerfold photo shoot despite being told “she wasn’t the right type,” invested in fake breasts (that she claimed made her millions), broke up with Hugh at the appropriate time when the right opportunity presented itself in Las Vegas to make money, and continued on from there.
I’m amazed at how complex and diverse human behavior when it comes to striving to survive and reproduce by attaining a good career and income. She did it in a way incredible way that’s foreign to me; my Asian American culture would’ve told me the chances of that worked were very slim or impossible and becoming an engineer or doctor is much more stable.
The book is a detailed memoir of how Holly Madison went from a smalltown girl to becoming the girlfriend of Hugh Heffner and Criss Angel.
I was surprised how Holly described Hugh and the environment around him. Some men regard him as a legend because of all the women he gets, but that was not how he was portrayed here.
She was drawn to the Playboy brand like most girls to improve her career. She didn’t get far in the nationwide auditions. Later, she had a chance to get into a party with Hugh in California. That opportunity got her invited to his mansion by the man himself, which she leveraged into staying at the mansion “temporarily.”
Eventually, she convinced Hugh to let her stay permanently, and after a long time, he made her his main girlfriend.
Once a permanent resident of the mansion, the girl gets a stipend for clothing, she gets the room paid for, special matching jewelry and costumes, and if you’re special, a car.
Inevitably, female-female competition and comparison erupt all the time, with Holly and others detecting the slightest difference between girls as a threat or sign of greater interest. Once, she noticed a girl had a larger room and calculated the extra cost per month she got. Another time, it was the car a girl got. And yet another time, it was the fact that a girl was able to wear red lipstick and Hugh didn’t get mad even though he flipped out when any one else would wear red lipstick.
Holly describes Heff as a man who uses the competition and comparison intentionally and manipulatively to his own romantic benefit and for his ego. I was astounded to see him as emotionally immature despite his business success. He was described as shrieking at girls, calling them ugly for a haircut or lipstick he didn’t like, and throwing a jealous fit over the phone after having his bodyguard follow Holly the one night she was away in Las Vegas (She chatted with Criss Angel for one those nights but claims she didn’t sleep with him — but she did ultimately become his girlfriend later on).
Despite all this, Heff gave her a naive perception of the whole system to Holly once, claiming that he thought he was simply making their fairy tale dreams come true.
Holly reveals all about the sex parties Hugh has, which occur weekly. Apparently, most of the girls don’t want to sleep with the old man. Holly herself have to deal with the stigma publicly of being with an old man a few times too. A couple girls will try their best to recruit as many new girls as possible so that they themselves don’t have to go. Just as described by another girl who said experienced it on YouTube, it is over real quick and he is on to the next girl.
The stigma of having to sleep with Hugh to be part of the mansion was implied but never explicitly stated. She also saw other girls lie explicitly that it wasn’t true when asked by others to protect their reputation. She also claims she saw many girls sneaking around with young boyfriends behind Heff’s back, but she never did and stayed loyal.
It seems women are attracted by the allure that the Playboy brand will have on boosting their career and earning power, along with the exclusivity of the parties and the wealth Hugh provided.
Many girls become regulars of the mansion but leave after four years when they feel it is “time to go” — just in line with when they have gotten all they can from the Playboy brand. Heff always begged the girls to stay when this occurred.
Holly was effective at using this to propel her career but it was never intentionally malicious or strategic. She even eventually got on a Playboy magazine cover even though she was a small-town girl and, as Hugh told her repeatedly, “didn’t have the model look” of the other experienced models. She persistently kept asking, and saw it as another comparison that measured her as less worthy than the other girls she was competing against at the mansion, and Hugh finally hooked it up.
I couldn’t find anything unique or eye-catching she that got her all the way to being Hugh’s main girlfriend, an incredible feat. She didn’t mention saying or doing anything extraordinare to get Heff’s initial attention at the party. Nor did she do so to turn her temporary stay in the house to permanent or to become the main chick. Maybe she was just the kind of good looking type Heff was looking for at the time. I don’t know.
Heff was painted as egotistical. He started going to nightclubs more often when he noticed it got him recognized and adored. He agreed to a reality TV show to get more fame. Holly claims she was the star girl in the TV show, and it cast her in a specific archetype along with other characters to make it more interesting but she was much more than the cookie-cutter character they had her play. She claims she made the show successful and when she left, the show started to decline. I’ve never seen the show to verify, but it seems a bit biased in her favor.
After deciding to leave the mansion, Heff begged her and even “accidentally” left his will at her bed with a sizeable amount going to her as enticement for her to stay. She still left and pursued a career in Las Vegas.
During her time in Vegas, she eventually started dating the magician Criss Angel. Criss was described as eventually becoming a hyper jealous man. His jealousy was even worse than Heff’s and it would erupt into many fights. What is it with all these rich famous people being so jealous? I guess it happens when your girlfriend is hot and famous — many guys could be threats.
Holly says that she later got her own show in Las Vegas and made millions from it. It seemed to have been some strip entertainment show, and I was skeptical if this claim was true or a lie to boost her reputation since I don’t think it’s that easy.
She mentions how the five-figure investment in her fake boobs had a tremendous return on investment. I guess this is one cases where plastic surgery may just well be worth it.
All these people seemed to suffer from some obsessive and weren’t secure, whether it was through comparison or envy.
That’s all I got for you! Please be somewhat respectful and kind in the comments.
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