Published June 20, 2023

Heidi Fleiss is an USA born, former madame. She ran an upscale prostitution ring based in Los Angeles and is often referred to as the “Hollywood Madame”.

In an exclusive interview with Fleiss, she reveals the price men would pay to spend the night with a woman playfully nicknamed ‘Barbie Doll’.

Heidi also divulges the unbelievable gifts her girls would receive from wealthy, sometimes famous, clientele.

Interview highlights:

  • $5k to spend the night with woman nicknamed the human ‘Barbie Doll’
  • Heidi had 2 girls who were given an apartment each from a client, as gifts for their talents

Heidi Fleiss became famous as Hollywood’s madame of choice in the 1990s. If you were a movie star or film-industry big-shot who wanted a prostitute, you called Fleiss and she sent over a girl who satisfied your desires.

While she’s generally too discreet to name names, at least one floats around. The actor Charlie Sheen outed himself when he testified to ordering girls from Fleiss at least 27 times. Names in her red Gucci book – including people who did not necessarily indulge in Fleiss’s favors – include the late billionaire Steve Bing and “Godfather” producer Robert Evans.

Following a headline snaring bust in 1993, Fleiss served time for her infractions. Now living a quiet life, north of Las Vegas, she spends most her days caring for dozens of macaws. Fleiss is indulgent enough to not care very much when the high-fliers all but destroy the interior of her red Bentley.

Away from the birds, Fleiss makes for a great running buddy in Vegas. I try meeting up with her whenever I’m in town and, invariably, we play blackjack together.

Fleiss is hilarious, engaging, and she vigorously enjoys gambling. She lets me count cards when she plays and generously allows me to jump in when the shoe gets good. Sometimes she’ll jack up her bets as I opt to play, but it still leaves her taking all the bad cards and sharing some of the good ones. For Fleiss, though, it’s mostly about taking shots, having fun, blowing off steam. Somehow, though, she wins more often than you’d expect.

Despite the fact that she has been out of the business of being madame for a number of years, she still knows plenty about the prostitution game. More importantly, Fleiss is happy to share details on the inner workings of commercial sex as well as how the girls should comport themselves and how much the guys should expect to pay.

These days, I wonder, how much would a customer have to shell out, per night, for a truly hot girl. “In the case of a girl I know, who I describe as a human ‘Barbie Doll’, for $5,000 she will spend the night with you,” explains Fleiss. “But by the time the night is over, if she is smart about things, she might leave with $20,000. When a guy has a girl he connects with, he doesn’t want to lose her and he’ll spend extra money to keep her.”

That said, adds Fleiss, the really smart hookers don’t go into a situation with a financial number in mind (from the customer’s perspective, however, proffering $5K is usually enough to close the deal for a tryst with the girl of your dreams). For the sake of the girl, however, says Fleiss. “The sum being paid should depend truly on how much the guy is willing to spend. The loser hustler asks for a sum of money up front” – say, $5,000.

A real hustler, a smart girl,” continues Fleiss, “if she knows that the guy is a billionaire or just garden-variety rich and willing to splash around money, she simply asks to meet him. No sum of money is discussed. She knows that if she meets him, anything is possible. Get inside the guy’s head and it won’t be just one night for $5,000 or $10,000. You can get a lot more – maybe even everything.”

Asked for an example of such a splurge, Fleiss doesn’t consider it for more than a couple seconds. “There was this one guy, I brought him two girls and they each got an apartment building after just a few weeks,” she recalls. “Of course, he had a lot of apartment buildings. But still…  The girls did not seem like they were hustling and got into his head. You let the guy pay you rather than laying down a number. Cap a night at $10,000 and you might want to kill yourself when you realize you could have gotten much more.”

For Fleiss, though, there was a major problem with the apartment building arrangement. “I couldn’t get my cut of the payment from the girls,” she said. “After that, I told the guys I dealt with, ‘No more houses, no more cars, no more buildings for the girls. Just give them cash.’ I don’t think anyone listened.”

Interesting as that may be, Heidi and I talk about more than commercial sex when we convene. We also talk about gambling. Following one of our blackjack binges, where I bet reds and greens while she wagers blacks, I confess to being such a nit that I won’t make a sports wager unless someone sharp gives me a pick or two.

“You have picks for this weekend?” she asks, reminding me that she is a longtime sports bettor who once provided girls for a party loaded up with players from the Cincinnati Reds, in town to play the Los Angeles Dodgers.

Figuring that the Reds would be exhausted after a night of frolicking, Fleiss bet $30,000 on LA. She lost the bet, though her thinking was in the right place.

I tell her I don’t have a bead on the coming weekend, but that I might be able to get NCAA sides from Alan Boston, a highly regarded college basketball handicapper who I met while reporting a March Madness story years ago. I visited his Vegas home to watch games with Boston and his crew. Placed on a coffee table was a bowl that appeared to be loaded with Smarties. I took a handful, dropped them into my mouth, and was surprised that at least one tasted bitter. I asked what was up and Boston distractedly told me that low-dosage muscle relaxers and opiates were mixed in with the sweets. As a pill’s pleasant effects crept on, I came to think of it as candy-roulette.

“Alan Boston?” she replies, familiar with him via a made-for-cable documentary. “I love that guy. He’s the sports bettor who takes care of dogs and wants to be an English teacher.”

I call Boston, requesting some picks, while knowing that he hates sharing them. It’s not because he’s tight with information, but because he’s an advantage player who makes his money by winning around 52%-53% or so of the time, which means that he loses 47%-48% or so of the time, and he hates to see recreational gamblers blowing money (that is impossible to earn back without always being in action) based on his say-so.

But when I mention Fleiss, his voice lights up. “Heidi Fleiss? She’s my last living hero.”

Suddenly, Boston turns as courtly as he gets. “Tell Ms. Fleiss I will give her some picks,” he says. “I respect what she does with the birds.”

It starts out great, with Boston going on a heater that has us running about 66% to the good. Every Saturday morning, Boston texts me the games to bet. I forward them to Heidi and we get down. Of course, she bets more than I do and keeps raising her wagers as wins pile up. By the start of March Madness, she’s ahead by some $35,000 and laying down thousands per game.

Boston is planning to visit Vegas for the waning days of March Madness. Coincidentally, I have plans to be there at the same time. Fleiss tells me, “If I was younger, Boston is a guy I could see myself going for.”

Boston confides to me that he wants to get a hug from Fleiss and hopes I can see how there would be resonance between them.

 I do.

Despite my telling Fleiss that she and Boston are approximately the same age, she insists that she’ll do something special for the man who has been feeding us these great picks. “I’m getting him a girl, maybe two,” she vows. “He’s going to have the best night of his life.”

Between that statement and the meet-up in Las Vegas, however, the wheels fall off for Alan Boston. I remember him once telling me about what happens when he “loses flow.” I witness it first-hand. My wins deteriorate, but things are worse for Fleiss, who’s betting peak sums at the start of March Madness, just as Boston loses his all-important flow. “I went from being ahead $35,000 to being down $25,000,” she tells me matter of fact. “But that’s okay. Alan Boston’s the best. He just hit a little bump.”

True to her word, on the night that we convene in Vegas, Fleiss has a girl for Boston. The girl, in fact, is Samantha, on whom deceased billionaire Steve Bing, according to Fleiss, spent $5 million over the course of three years. I suspect that she is the human ‘Barbie Doll’ Fleiss had referred to during our blackjack session. She surely looks the part.

Boston is unaware of Samantha’s purpose that night. We eat vegan Thai food (he and Fleiss both avoid meat) and talk about gambling adventures while an acoustic guitar player incongruously plays country classics in a corner of the restaurant. At meal’s end, Boston gets his hug from Fleiss, and he Ubers back to where he’s staying. I’m wondering what the hell is going on as Fleiss, Samantha, and I proceed to the D Las Vegas to play blackjack. I win a couple thousand, Fleiss wins $6,000, and Samantha keeps close enough track of Fleiss’s money that she corrects me when I comment that Heidi won $5,000.

Back in my room, I call Heidi to talk about how ill-fated the night was. “I’m definitely losing my touch,” she tells me. “All somebody had to do was take Samantha’s hand and she would have gone home with him. I already paid her $5,000 for the night.”

I remind Fleiss that nobody really knew how it worked and Samantha was indeed beautiful. Fleiss’ touch remains intact. She laughs it off and we both have a story.

The next day I tell Boston what unfolded, that Samantha was there for him. Despite her good looks and the generosity of Fleiss, he sounds unimpressed. “Getting oral sex from a stranger is the most uninteresting thing imaginable,” he says. “I was there to talk to Heidi.”

Never mind that things didn’t turn out as expected, Heidi is hoping to get picks from Boston for the coming NCAA season, Boston has since checked in to see about being put in touch with Heidi and Heidi has reached out to him. Meanwhile, she remains preoccupied with her birds and is engaging in a new form of procurement: finding blue-chip art for gold-dipped collectors, being the conduit between those who own rare multi-million-dollar paintings – think Jackson Pollock and Pablo Picasso – and those who want to acquire them.

How different is that from hooking up drop-dead gorgeous females with deeply generous males for sex? “They’re both advantage plays and not so different,” says Fleiss. “It’s knowing what people desire, treating them right, and making them fall in love—whether it’s with a canvas or a girl. It’s all the same thing.”

And, no doubt, she will not put a cap on the price of an artwork.


Michael Kaplan

Michael Kaplan is a journalist based in New York City. He had written for publications that include Wired, GQ and the New York Times. His article on Kelly “Baccarat Machine” Sun and Phil Ivey is being developed for a feature film. Michael received a BA in journalism from Glassboro State College — the very school that Patti Smith got kicked out of for getting pregnant.