Heidi Fleiss Reflects on 25th Anniversary of Her Arrest, Ex Tom Sizemore and What Charlie Sheen Really Spent on Girls

It’s hard to believe it took until 1993 for someone to earn the nickname “The Hollywood Madam.” That honor went to Heidi Fleiss, one of six children born to Paul Fleiss, a popular Los Feliz pediatrician. In 1987 and at age 22, Heidi was taken under the wing of Madam Alex, a procuress to the stars, to whom Fleiss was introduced by her filmmaker boyfriend. She first worked as one of Alex’s call girls but quickly absorbed the business and launched her own prostitution service in 1990. With a knack for recruiting high-end talent, Fleiss by 1991 had amassed a stable of 500 girls — the look was “clean-cut and perfect, [like] she was born and raised in Beverly Hills,” she once explained — who charged clients about $1,500 a night ($2,800 today), of which Fleiss took 40 percent. Soon she was clearing $300,000 a week ($560,000 now) as she kept an A-list roster of celebrities and Hollywood executives very satisfied. Her infamous “black book,” which contained the names of her famous clients, was actually a 28-page red Gucci planner.

The party did not last long: On June 9, 1993, Fleiss was arrested and charged with five counts of pandering. “The other players like Madam Alex were all working with the LAPD, giving lists of their clients on a weekly basis,” says Nick Broomfield, director of the 1995 doc Heidi Fleiss: Hollywood Madam. “Heidi wouldn’t play the game. She broke all the rules. She kind of did it for fun, which was why she was so successful.” The case went to trial, where Charlie Sheen testified he’d spent $53,000 a year on Fleiss’ services. A jury convicted her on three counts, for which she received a three-year sentence. That conviction was overturned in 1996, but a federal tax-evasion case the next year led to a 20-month stint in prison in Dublin, California.

Today, the 52-year-old Fleiss lives with dozens of exotic birds on the outskirts of Pahrump, Nevada. She spoke to The Hollywood Reporter about her lasting place in show business infamy. 

So it’s the 25th anniversary of your arrest.

That didn’t cross my mind until you mentioned it. I feel like this: Everything in my life — even my fuck-ups, and there’s been a ton of them — everything worked out right because it led to exactly where I am right now. Most people would think I’m a kook, because my heart goes out to the captive macaws. You know what a macaw is?

It’s an exotic bird?

Yeah, a parrot. The big ones. I think every day in prison was important because it made me realize how awful it would be if someone forced you to live your entire life inside a box. And that’s what happened to these captive macaws. It’s not a popular subject matter. They need someone who’s a little bit kooky like me to stand up for them.

How did you end up taking up the macaw cause?

I moved to Nevada to get it back into the sex business. I rented a house that unluckily for me happened to be next door to a retired madam who was bedridden. At one time she ran the exotic bird department for the Tropicana Hotel. So she had all these birds. One night she called me up at three in the morning saying she couldn’t breathe. I went there as a helicopter was taking her away. As she’s dying, she says, “Heidi, you take care of the birds.” 

At the time of your arrest, it seemed like you were leading a pretty glamorous existence.

It was a lot of fun. Of course looking back, you see how stupid you were. It’s easier to look at all your mistakes. But I definitely say if you’re going to live in L.A., I don’t see how anyone can do it better than I did. You want to go out to every nightclub. You want to meet famous people. Have sex with different people. Eat at the best places. All that kind of stuff. And I don’t see how it could have been any more fun, that’s for sure.

You came from a fairly conservative background. Your dad was a doctor.

I was born and raised in L.A. My dad was a famous pediatrician. When he died, they donated a bench to him at the Griffith Park Observatory.

Did he know about your escort service?

No. But I got him in big trouble. I felt shitty about that. Dad gave me really the best childhood possible and all of the opportunity in front of me. I wish that I took school seriously and went a different route, but it was not my father’s fault at all.

You learned a lot from another famous madam, Madam Alex.

Hell, yeah, she was crazy. She was out of her mind. But it took a lot more than just learning from someone. There’s a lot more thought that goes into the escort business than people realize. You have to learn how to make people feel secure in dealing with you.

So you’ve let go of this idea of running a male brothel?

I think a male brothel wouldn’t work, but a transvestite brothel would probably do really well. I live in Pahrump, Nevada. It’s kind of near where [Khloe Kardashian’s ex-husband Lamar Odom] overdosed in a brothel. My good friend Dennis Hoff owns all the brothels in Nevada. He has an extra license he’s not using. So I was thinking maybe we could make it a trannie brothel. I can see people driving an hour away to the middle of the desert if there’s this beautiful trannie waiting there for them.

Are you dating anyone or single?

Not right now.

I saw some headlines that your infamous “little black book” was being sold on eBay. 

I called eBay and I stopped them. That’s stolen property. It was the same weird people that were once latched on to Stormy Daniels — [Daniels’ ex-manager] Gina Rodriguez and [Daniels’ former lawyer] Keith Davidson. They’re really strange. They were the ones that were doing it.

How did they get it?

A TV director had a couple pages. That’s what I figure they were selling. 

So you still have the little black book?

No. Kind of. Why does this even matter anymore?

Was it not subpoenaed as evidence? How come the prosecutors never got their hands on it?

I don’t know, actually. It was just something that seemed very private and personal that was no one else’s business. That’s just how I feel about it today and I always felt. I was offered a lot of money to sell that book. And there were times when I really needed that money. But that was never something I would do.

What do you think about Harvey Weinstein’s accusers and the #MeToo movement?

I’m not going be like Donna Karan and kill my career, or like Pamela Anderson. They say it’s the women’s fault. I will never do that because, look, every girl has been sexually taken advantage of. I think he’s disgusting and a pig. He handled this thing terribly. But some of it doesn’t make sense to me. Especially when they say, “Oh, it happened six times.” That’s weird. I think in certain instances, women slept with him in exchange for a part, and he kept his end of the bargain. 

Have you kept in touch with former client Charlie Sheen?

No, I’m not friendly with Charlie Sheen. But I like Charlie Sheen. I like that he just does what he wants and he pays for women. But I think it’s terrible they blackmailed him [over his HIV diagnosis]. Big deal. It’s not like AIDS is a deadly disease anymore. It’s better than having asthma. You just take a medication. Diabetes is worst than AIDS. It just has a stigma attached to it, but it’s not a big thing.

Why did Sheen end up going public as a client during your trial?

The only reason his name came out is that when I was arrested, I had travelers’ checks in my purse with his name on them. On the stand he said a much lower amount than he actually spent with me. He probably spent closer to $300,000 or $400,000 on girls. He said something like $60,000.

How are things with your ex-boyfriend Tom Sizemore, convicted of abusing you in 2003?

We had done those drug addiction shows together — Dr. Drew. Afterward we were friendly and he’d call me every now and then. He’d act like he had his stuff together. But it was all a lie. Everything is a lie. I brought him to a Humane Society event at Paramount Studios last year. He was just such a mess. So out of it. He stole money from my purse. He’s such a drug addict because he’s so afraid of being fat.

Fat?

Yes. He once did some movie with Will Smith, Enemy of the State, where he was, like, 280 pounds. I like a heavyset guy. But he is so afraid of being fat. That’s what his addiction is about. It’s all narcissism. It’s gross. I guess after #MeToo, some reporters were calling me about Tom touching a prepubescent girl — like an 11?year?old little girl — inappropriately. I don’t know what to say. I don’t know if that really happened. If it did, he should be castrated. That is so disgusting to me.

Did he ever show signs of that when you were together?

No. He liked horse porn, though. He did like horse porn. This one woman that would have sex with a horse on the internet, he told me that’s his favorite actress. “Better than Meryl Streep.”

Have you stayed sober?

I struggle. I struggle with my addiction. And it’s tough because I’ll be doing so well. And I don’t know what will make me flip. 

Maybe being isolated in the desert doesn’t help.

I don’t know. Sometimes I’m really glad that I’m here. We all have a lot of pain. And I really hurt for these birds. I wish I can do more for them. I know I’ll never be able to help all of them, but maybe if I could just create a place where, when people don’t want them, they can live out their life without a cage.

A version of this story first appeared in the June 6 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.