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ONTD Original: Uncovering the Identities of the Playmates in Holly Madison's Book

Readers of Holly Madison's new book Down the Rabbit Hole all seem to have the same burning question on their minds: who exactly is she talking about? As expected, Holly chose to change the names of many of the playmates and girlfriends she describes throughout the story. That decision to protect the innocent -- and, of course, the not-so-innocent -- has, unsurprisingly, only made people that much more curious about which real-life girls are protected behind the pseudonyms.

Who was "Vicky," the truly evil girlfriend who constantly bullied Holly, reportedly recruited other girlfriends and playmates to become escorts, and was eventually kicked out of the mansion for breaking Hef's rules by SELLING spots on her guest list to the smaller mansion parties?  And who was Lisa, the baby-faced Anna Nicole Smith lookalike who actually showed Holly some kindness? Who were the "mean girls" that treated Holly and Bridget like dirt? Who was the girlfriend who slept with Jennifer Lopez's ex-husband, Cris Judd?

Well, I researched so you don't have to. And let me tell you, it took a long-ass time. Back in the day, Hef's girlfriends were almost never mentioned by name in the descriptions of photos taken by the press. There were simply too many and they rotated in and out of the group far too quickly. The fact that they were all thin, snub-nosed, buxom, and platinum blonde didn't help either, making actually identifying who was who in any given picture incredibly painful.

In order to figure out just who was really living at the mansion when Holly moved in, I had to make a little timeline:

MARCH 2001

  • In an article about Hefner’s 75th Birthday celebration, his girlfriends of the moment are listed as: Cathi O'Malley, Buffy Tyler, Tina Jordan, Tiffany Holliday, Stephanie Heinrich, Kimberley Stanfield, and Regina Lauren. Katie Lohmann is described by other sources (notably Izabella St. James in her book Bunny Tales) as being a girlfriend around this time as well.

Over the next few months, the majority of these girls leave. In the few months before Holly even moves in, St. James notes that:

  • Cathi O'Malley moves out.

  • Buffy Tyler apparently drives her new Escalade (a gift from Hefner) to Texas to see her secret boyfriend, and is immediately kicked out as a result.

  • Katie Lohmann moves out after becoming POTM April 2001.

The newly departed girlfriends are eventually replaced by Dalene Kurtis, Kim Stanfield, and Michelle Winchester.

(Above: May 16, 2001. Caption: Hugh Hefner, laughs as he for poses pictures with his seven girlfriends (L to R) Tiffany, Tina, Michelle, Dalene, Stephanie, Kimberley and Regina on May 16, 2001)

MAY 2001

  • Consistent with St. James' account, Cathi O'Malley, Buffy Tyler, and Katie Lohmann are no longer Hefner's girlfriends by this time. They have been replaced by Dalene, Kimberley, and Michelle.           


  • Regina Lauren is kicked out for selling Hefner's personal belongings (according to St. James).

  • Christi Shake moves in, becoming Hef's newest girlfriend.


  • Girlfriend Kimberly Stanfield is kicked out after becoming POTM July 2001, leaving an open spot for a new girlfriend.

  • Several of the girls start asking Holly to come out clubbing with them and Hef. She begins hanging around the mansion even more frequently.


  • Holly moves in around early September 2001. She stays in Rm 3, along with "April," the only roommate she will ever have at the mansion until she eventually moves in to the private bedroom of Puffin himself.

So let's step back and use some deductive reasoning.

At the time Holly moves in, the girlfriends must be: Christi Shake, Tina Jordan (oldest + main girlfriend), Michelle Winchester, Dalene Kurtis, Tiffany Holliday, and Stephanie Heinrich.

Holly lists the live-in girlfriends at this time as: “Vicky”, “April”, “Lisa”, “Adrianna”, a quiet girl named “Carolyn,” and #1 girlfriend Tina Jordan. Ready for a who's who of Down the Rabbit Hole?


"April" = Christi Shake
Why? Holly says that "April" was her roommate in Rm. 3 when she first moved in. St. James corroborates that Holly immediately moved into Rm. 3, and that her roommate was none other than Christi Shake.

Revelations about "April"/Christi:

  • intimidated the hell out of Holly

  • taller and bigger boned than Hef’s usual type

  • in-your-face personality

  • became a Playmate at some point (Christi became POTM May 2002)

  • Holly didn't like her, and neither did the other girls apparently


"Lisa" = Stephanie Heinrich

Why? A few weeks after Holly moved in, she started hanging out sometimes with "Lisa," who was celebrating the recent release of her centerfold.
Which girlfriend had a centerfold released around that time? None other than Stephanie Heinrich, who was POTM October 2001!

Why else? Because Holly notes that after her centerfold was released, she moved out a few months later. Which Stephanie did. And what did "Lisa" do after she moved out? Holly says that rumor had it that "Lisa" ran through her savings in a few months and had to move back home, despite working regularly with Playboy Productions. Stephanie Heinrich, after leaving, moved back to her hometown of Cincinnati, Ohio, and worked sporadically for Playboy up until at least 2013.

Revelations about "Lisa"/Stephanie:


"Adrianna" = Dalene Kurtis

Why? Because Adrianna was the only other girlfriend at the time that was an upcoming centerfold when Holly moved in. Tina Jordan would later become a centerfold, but Holly referred to her by name, so it wasn't her. And Tiffany and Michelle never became playmates. Leaving only Dalene as Adrianna.

Why else? Like Holly, "Adrianna" had also been a Hawaiian Tropic girl. And, you guessed it, so had Dalene, who was discovered by Playboy after appearing in the Miss Hawaiian Tropic Pageant!

Revelations about "Adrianna"/Dalene:

  • Became a centerfold almost immediately, so the other girls were mean to her

  • Wasn't close to Holly, but wasn't mean either

But most importantly...DRUMROLL PLEASE...


"Vicky" = None other than miss natural beauty herself, Tiffany Holliday.

How do I know?

  1. Holly says that right around Halloween 2002, "Vicky" and the "mean girls" went and got Playboy bunny tattoos. When they got back, Hef confronted them about their rule-breaking moneymaking scheme: they had been caught SELLING invites to mansion parties, something that was very much off-limits. The invites were supposed to be for close friends and family, but "Vicky" and co. would write down the name of anyone who was willing to pay up, claiming that the person was their cousin, friend, whatever.

  2. In Izabella St. James' book, she describes a night around Halloween when she, a girlfriend she calls "Emma," and a girlfriend she calls "Tammy" all went and got Playboy bunny tattoos. And that upon returning, Hef was mad at them, having discovered their invite-selling business. She goes on to say that "Tammy" was kicked out because of it. St. James claims that Holly tattled. Holly denies this.

  3. Writing about the forced departure of "Tammy," St. James writes, "I knew [Hef] cared about [“Tammy”]. He was also sorry to see her pets go. After all, he had bought her Pinky, the capuchin monkey, just a few months earlier."

  4. Now, who has a capuchin monkey named Pinky? TIFFANY HOLLIDAY. In one interview, when asked about her pet monkey, she said, "Her name is 'Pinky' and she's a black-capped capuchin, native to Brazil. She was a gift from Hef while I lived at the mansion."

If "Vicky" = "Tammy" and "Tammy" = Tiffany Holliday, then by the transitive property, "Vicky" = Tiffany Holliday.

Revelations about "Vicky"/Tiffany:

  • At first nice to Holly, but turned cruel as soon as she moved in. Was the queen of the mean girls in the house.

  • Kept a steady stream of new girls coming up to sleep with Hefner, which she had realized was good for her because then SHE didn't have to do it as often.

  • Tried to recruit Holly to become an escort. Holly notes that she came to believe that Vicky was working as a recruiter for famed Hollywood madam Michelle Braun, who was known for having a number of Playmates as "employees" and had told a reporter in 2009, "At one time, seven of the eight girls living in the Mansion were working for me. I had one of his girlfriends in the Mansion just to recruit for me.” Holly concludes that "Vicky" must have been said recruiter girlfriend.

  • Other girlfriends confided in Holly that "Vicky" had also asked them to become escorts. One said that Vicky got a cut/fee for every new girl she introduced to Braun.

  • Once had sex with Jennifer Lopez's ex-husband, Cris Judd, by asking him if he wanted to come upstairs and "see her monkey"


(Above: "Mean girl" Izabella St. James)

Besides Vicky, the two other "mean girls" who went and got tattoos and were participating in the invite-selling business were Izabella St. James (as she admits in her own book) and a girlfriend who is referred to by St. James as "Emma." I did some snooping and "Emma" is Zoe Gregory Paul (St. James tells a story of how Emma lied in an interview back home in Britain about a night with Justin Timberlake in the Grotto...who else did this very specific thing? Zoe Gregory Paul!)

123456 + Down the Rabbit Hole by Holly Madison + Bunny Tales by Izabella St. James

Buzzfeed/other websites if you steal this without permission and/or crediting me I swear to god...

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