[Book] Down the rabbit hole / Holly Madison

In case you aren’t familiar with Holly Madison, she is best known as Playboy magnate, Hugh Hefner’s girlfriend number 1 (of three…) from 2001 to 2008. I am familiar with Holly thanks in part to the TV show the Girls Next Door, which aired on the E! Channel for six seasons. The show was somewhat of a guilty pleasure for me as it showcased a shallow slice of life of three gals (Holly Madison, Bridget Marquardt and Kendra Wilkinson) living together in the historic Playboy Mansion, competing for Hefner’s affection. I was fascinated with how these girls were willing to put up with all this bullshit; each other, that dated manor, and that old bag Hef. The show made it all look like they lived in a perceived lap of luxury.

Holly Madison’s take on this life is detailed in her autobio, Down the Rabbit Hole. The book tells of Madison’s humble awkward beginnings in Oregon, her part time job at Hooters while in college, becoming a Hawaiian Tropic model, and then catching the eye of Playboy scouts that landed her a room in the Playboy Mansion, that eventually got her a part in Hugh Hefner’s harem. Her climb to success came swiftly….and according to her, it all came at a price.

According to Madison’s book, not shockingly, Hef treated the girls as a business. Along with a roof over their heads, the girls received a monthly stipend of $1000 to be used to ho themselves up in lavish frocks and jewelery so they could make Hef look good while he went out clubbing; a twice a week ritual. As Holly tells it, the money was accounted for to the cent; no using it for maxi pads or doritos! Hef’s scouts would predatorally seek out struggling girls starving for fame with a hope for a Playboy cover and a modelling deal. According to Madison, most of these girls never got the cover (Holly and the other two FINALLY did, but after the show gained traction). Almost all the girls in his entourage were in financial cul-de-sacs; strapped with debt in student loans or just plain no money. Hef would NOT help them out financially with their bills, however; he was struggling financially himself, as we all know how the magazine industry started falling into a tank around that time. Every girl needed to work outside of the Mansion to pay their own bills bills bills. All the while, they had to reconcile Hefner picking and dropping girlfriends on a whim without consequence, and no girl had a say in the matter. Jealousy was prevalent, and after all this, they still had to sleep with him (*shudder*).

As entertaining as Down the Rabbit Hole was, I could not wrap my head around putting up with Hef. Back when the Girls Next Door aired, I recall Holly Madison defending him and the relationship constantly in the media, and even saying she wanted to marry him. In this book, she says in retrospect it was like she was in a trance; she was naive, and simply put, she lost her damn mind (no, really?). She whines endlessly about Hef and the “family dynamic” involving the other girls. She sounds pretty soured and a bit defensive by the whole experience and it comes through in the book’s delivery. But, let’s be real, Holly: you had everything to gain being with Hugh Hefner – ya got yer a$$ on Playboy, got some fame, eventually got your own TV show and married a rich younger dude, for what it’s worth. Her bills bills bills got paid paid paid thanks in part to that old bag.

Down the Rabbit Hole ain’t no War and Peace. But, it was a slice…it’s an interesting read if, a little gossipy.


Down the rabbit hole / Holly Madison


  1. I gotta say. You’re not really selling the book well. Haha. Does it at least open your eyes to anything new or was it all what you expected?

    Liked by 1 person

  2. Good grief! That show is real? Jings. The things folks do for 15 minutes, huh?

    Interestingly, I was watching Jim & Andy the other week and laughed a bit at the stunt Jim and Andy’s old prankster chum pulled on ol’ Hugh at the mansion.

    Liked by 1 person

  3. I never understood what the appeal was, myself, so my first thought was why did she stick around that long? No one is naive and in a trance for seven friggin’ years under those circumstances. Are they? Weird. It’s almost like a cult. The cult of T&A. The cult of Cornfed Airbrushed Blondes. Oh wait, even better, the cult of BEWBS!

    Is there any mention of why she waited around til after he died to publish the book? I mean, it was gonna tarnish his reputaion (such as it was) anyway.

    Good on ya for sticking it out and finishing the book.

    Liked by 1 person

  4. Ahh yes Girls Next Door…this could be in my blog of ‘Wacky Shows I’ve Been Paid To Watch’ …..and I didn’t mind watching at alllll. Of course we had the Canadian uncensored version so it had some bonus appeal….
    Holly was for sure the lead Girlfriend and to me played the role with the most strategy. She seemed to have a clear plan to financial freedom…get a ring and/or a baby from him. She could humour everything else while on this quest


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