20 Questions: Heidi Fleiss

She was among the most powerful women in town. From 1990 to 1993 she had a direct line to A-list stars and studio execs, running the most exclusive call-girl service in Los Angeles. At one time, Heidi Fleiss employed more than 100 women. She did well. So well, in fact, that she soon moved from a two-bedroom West Hollywood apartment to a $1.6 million Beverly Hills home. Among her neighbors were Bruce Spring-steen and Jay Leno.

Then in June 1993, the dark-haired daughter of a prominent pediatrician was busted for pandering and drug trafficking. In December 1994 Fleiss was convicted on three of five counts of pandering but was found not guilty of the drug charges. The penalty: a possible eight years in jail. Federal charges of income tax evasion, conspiracy and money laundering followed, of which she was also found guilty. We sent Contributing Editor David Rensin to meet with Fleiss and see what the former Hollywood madam had to say for herself as her sentencing date loomed.

1.

[Q] Playboy: By the time this interview appears, your sentence will have been determined. Care to predict the outcome?

[A] Fleiss: I read the report. I know my probation officer recommended seven years and three months in a federal institution, and that I'll serve six complete years. It's terrible, it's awful. Somehow I seem to piss off an awful lot of people. I know I was power-tripping and that I made the wrong kind of enemies. But I've been good. I was arrested three years ago. I've been a model citizen. I pay my taxes, I employ 15 people at my store. I'm a perfect example of a reformed criminal, and I think that the system could actually use me. I'd be better used in some kind of community service than to be stuck in a cage some-where. I had hoped that there would be some bigger minds out there. Being imprisoned for consensual sex is archaic. Child molesters and murderers get probation. It's not fair. I was arrested, I stopped what I was doing. I live a totally different life now. The police accomplished their goal.

2.

[Q] Playboy: When guys go to prison they are afraid of being raped. What do women think about?

[A] Fleiss: I wish that I knew. I have all these attorneys and no one knows of a good women's facility to recommend because they have had little experience with women's federal crimes. I don't know where they sent Leona Helmsley, but if she could handle it I can handle it.

3.

[Q] Playboy: In Nick Broomfield's documentary Heidi Fleiss: Hollywood Madam, there was talk of a $40,000 fantasy night ordered by one customer. What does a guy get for that kind of money?

[A] Fleiss: He gets me in attendance, talking. That's the bonus. We had a lot of fun during the fantasy nights. We did them once a week. One of my customers liked this certain girl, and I would go there with her and two other beautiful girls. She would start stripping by the fireplace. We'd each take a quaalude. Everyone would get loose. Then she would give the guy head while I made up stories—some were true and some weren't—about things that went on while she did tricks. She would make him come, then the other girls would make him come. I guess for $40,000 you get a sex orgy. Everyone had a good time. There was nothing humiliating or degrading. How could you not be satisfied with the evening? If a guy comes ten times a night, he's a happy guy.

4.

[Q] Playboy: When did you realize, growing up, that you were different from other girls?

[A] Fleiss: I was 16 when I "strayed." I was at the racetrack instead of deciding what sorority to join. I was always hanging out with boys. I liked sex. Although I didn't have sex until later. I liked gambling. I was attracted to risk. It was something that got my heart pumping. Being at the racetrack thrilled me more than whatever other girls were doing. But I didn't have trouble relating to women. I had tons of girlfriends, and I was always the group leader. That's probably why it was so easy for me to make the transition to what I call being a go-between. I don't view what I did as running a prostitution ring. It was more like a dating service.

5.

[Q] Playboy: Should prostitution be legal?

[A] Fleiss: Yes. It could be regulated. It should be a woman's choice so long as it's not used to feed a drug habit, and no one should be forced into it. Beautiful girls come here from everywhere and want to be actresses and movie stars. To me, prostitution is a steppingstone, not a career. I can't mention names, but maybe somebody worked for me once or twice, and that was enough to get her the money she needed to jump ahead. But you never hear the success story of the girl who fulfilled her fantasy of sleeping with a famous guy, traveling through the Caribbean for $2000 a day, having a great time that one time, then going on and being successful at whatever she does in life. All you hear are the loser stories.

6.

[Q] Playboy: Rate the best-seller You'll Never Make Love in This Town Again. Given the book's success, are you sorry you passed up the offer of a million dollars to write your own book?

[A] Fleiss: I read some of the book and it cracked me up. Some of it's funny, much of it is old news. Who really cares? I believe that when you get home and close your door, whatever you do behind it is your business. Plus, the four authors are so stupid. I saw Liza Greer on Geraldo talking about how many times she tried to kill herself. It's not Hollywood's fault she tried to kill herself. That's her fault. No one made her take a razor blade to her arm. You can come to this town and be whoever you want. She chose to be a freebase head, a crackhead. I saw the contracts before the book was published. Samantha Burdette was living with me at the time, and Michael Viner, the publisher, faxed over her contract. I told her, "You know, if you do this book you can't live with me anymore." "Oh, but Heidi...," she said. They're very stupid girls. I was offered a $5 million package for a book and a movie, and I have the faxes to prove it. But I didn't write a book. I never named one name. When I was arrested, everyone said my clients were so scared. No one was scared. They all knew I wasn't going to say anything. There are some scumbags I truly would like to hurt, but I just don't have it in me. I believe there's a future in making money without hurting people.

7.

[Q] Playboy: After you were arrested, what fabulous offers did you get to keep quiet? What would you like to say to all the guys you didn't name?

[A] Fleiss: No one ever helped me out with a dime toward my legal fees. No one has done anything. Don Simpson spread a rumor that he paid my legal fees. When I met with private investigator Anthony Pellicano, who needed some information from me, I said, "By the way, tell Don to either quit telling people he's paying my legal fees or to really pay them, because maybe there's someone out there who will pay them and he's hindering it." So here's what I'd like to say: Please pay my legal bills. I'm with Gibson, Dunn and Crutcher. Just call them. You can wire money right into the account. I think the outstanding bill is up to 200 grand. Please, just wire the money right over.

8.

[Q] Playboy: Most men imagine that beautiful women are incredible in bed. Some contend that beauty is no indication of prowess. Give us your expert opinion.

[A] Fleiss: One guy will go, "Oh my God, you've got to sleep with Amy. She's the best fuck on earth." You sleep with Amy and she's a dead fish. It's all chemistry. It's between your ears. I'll tell you what a guy does not like. Say he's paying $2500 for a girl, and he gets one who looks like Elle Macpherson. She walks in with the attitude of, "You are lucky to be paying for me. You're lucky." A guy would rather be with a B-level or C-level girl who comes in and says, "Hey, come on! Let's whatever—watch a porno film or drink some wine." He wants someone who has energy and starts doing a 69. Who wants to be with someone who wants you to think that you're lucky? Take a fucking hike. Who said you have a golden pussy?

9.

[Q] Playboy: Which actress who has played a hooker might make a good one in real life?

[A] Fleiss: Elizabeth Shue. She looks like a few hookers who worked for me. It was tough to see Leaving Las Vegas because I wanted Nicolas Cage to go into rehab saying to Shue, "I love you and I'll get better and marry you, and we will be happy." Instead they did the story realistically.

[A] Julia Roberts, too. In my attorney's closing arguments he said to the jury: "Pretty Woman was one of Hollywood's biggest blockbusters. Did you hate Julia Roberts? Were you mad at her and Richard Gere for playing those parts?" The jury giggled, as if thinking, Why should we be mad at Julia Roberts for playing a hooker? I loved Pretty Woman. It's weird how our society is so hypocritical. Maybe the message is that the laws have to change.

[A] I'd also say Michelle Pfeiffer because she's beautiful—not that she played a hooker. But she was practically one in Scarface, which is one of my all-time-favorite movies. When I was arrested I thought I was Scarface. I said, "Set my bail, any bail. I'll make bail in two hours. I don't care; make it any price." I'm tripping on like I'm Tony Montana.

10.

[Q] Playboy: What are your rules for surviving in Los Angeles?

[A] Fleiss: Pretend. The town is too small to have enemies, especially if you're in show business. Even if you don't like someone, make believe you do. It doesn't mean you have to do business with them. Also, you don't want to make enemies with the police. If I had it to do again I wouldn't make those enemies. A bizarre example is the death of Don Simpson. I read what some people said about him after he died, and the hypocrisy kills me. Some of the people who eulogized Don hated him. To me, Don Simpson was an inspiration. Here's a guy who was from a shoe box in Alaska, poverty stricken, weirdest parents on earth, told him every day he was going to hell. Then he came to Hollywood and made his dreams come true. It shows that people can do anything they want if they apply themselves. Some said, "Oh, well, Don was into weird sex." Yeah, well, these people sat and watched with him. Simpson just wrote the checks. So he liked to do kinky things. I didn't supply him with the kinky girls. Don was Madam Alex' client. Actually, her bread and butter.

11.

[Q] Playboy: Where are your little black books? Does the law enforcement community know something the rest of us would like to know?

[A] Fleiss: [Smiles] The FBI has them. They took four. They can't understand anything in them. I wrote everything in code—I was probably high out of my mind, writing the best gibberish on earth—and they can't break it. They've called their top people. I don't think I'll ever get them back. I would like them back. They are decent Gucci books. They probably cost $400 or $500 apiece. Come to think of it, I could probably sell little black books in my store. Day Runners. Hmmm.

12.

[Q] Playboy: Say the first things that pop into your head. Charlie Sheen. Billy Idol.

[A] Fleiss: Sheen: hate him. He did his deposition on video. He didn't even have to go into a courtroom because he's Mr. Hotshot. When they asked him sexual questions, he got all excited. I bet he had a hard-on during the interview. He said, "Oh yeah, I saw a different girl every day for two months straight, and gave them two grand at a time in cash." That's a complete lie. He never, ever paid cash. He always wrote checks. Good thing they never bounced. I think his career is over. That guy is the biggest loser.

[A] Billy Idol would get so fucked up and high, he'd want girls to shove everything in sight up his butt. I don't think a girl gets too much pleasure out of that, to be honest. Plus, he wouldn't even pay. Billy Idol was my groupie. He would hang out where I was. I found him repulsive.

13.

[Q] Playboy: What are the ideal features for one of Heidi's girls?

[A] Fleiss: A hard body is ideal. It doesn't matter what kind of hair, what size tits. Just a beautiful face and a hard body. Every man has something that turns him on. Some guys say, "I must have a girl in red high heels and those fingernails, and a garter belt." Some guys say, "Tell her to come in jeans and tennis shoes." I like older men; everyone knows that's my preference.

14.

[Q] Playboy: You used to live with international financier Bernie Cornfeld. What's the most romantic thing someone with millions of dollars can do for a woman like you?

[A] Fleiss: Some of the châteaus in weird parts of France and Switzerland have been converted into restaurants. We'd have dinners there: a 12-course meal with wines so old they're from before George Washington's time. I've experienced things that some people will never get to do. I remember waking up in Bernie's castle and looking out a window that some king once looked out of. Those are things you never forget. I (continued on page 149) Heidi Fleiss (continued from page 116) remember the first time I saw Bernie's house, the Greyhall mansion in Beverly Hills. I said to another girl in the car, "Just show me who owns this house." Then I saw Bernie, this little man who looked like Santa Claus. I was like, "Ah! My life, easy street." Little did I know it was the roughest street I was ever going to travel. I was so young when I fell in love with him. I didn't quite understand sex. I was exposed to this world of private jets and helicopters and money. We're buying a hotel here, we're doing something else there. I went to homes that had staircases made of 24-karat gold. And soon it became normal. I guess I got into it so young that I got caught up and expected things to be like that forever. But after a while I got tired of Bernie's whole show. When I met Ivan Nagy and Madam Alex, they were the two creepiest, weirdest people I had ever met in my life. But in a real sick way I was fascinated by something other than Bernie's helicopters and jets and châteaus. The fascination with the bizarre made the transition easier. I had no idea that the consequences would be so severe or that I would become infamous. And still, kids come into my shop all the time and say, "You're my idol, Heidi. You're the coolest." When that happens I say, "No, I'm not. You be good. Don't do drugs. Stay in school. Listen to your parents." I don't know if I'm telling them the right stuff, but I try. I wouldn't want anyone to go to sleep at night and think of what I think of: prison. It's no way to live.

15.

[Q] Playboy: Your relationship with the legendary Madam Alex—before you, she was the queen of Hollywood madams and you worked for her and learned the trade—was clearly volatile. Did she have any final words for you before she died?

[A] Fleiss: "I love you, you're my baby." She kept crying, "Mommy, Heidi, Mommy," and when she did the hospital called me. I'd go and also sign T-shirts for everyone on the floor—the doctors, the intensivecare staff. They called me so much—I was about to start my federal trial and be put in jail for maybe up to ten years—that I finally told the hospital, "Look, I'm not even family." I did what I could. It was a weird love-hate relationship, but I guess I loved her more than I hated her. We had a bond that only she and I could share. She was wise. She was negative. In a sick way, I was the daughter she never got to abuse. Or she did abuse, maybe. I was there to the end.

16.

[Q] Playboy: Your dad, who is a pediatrician, lectures against circumcision. Do you have a position on that issue?

[A] Fleiss: When you think of it as a part of the body being cut off, it's strange and frightening. He's probably right. A man is probably born with a foreskin for a reason. I couldn't care less if a guy is circumcised. I've had sex with plenty of guys who weren't circumcised, and it was good sex.

17.

[Q] Playboy: As a service to the American business community, tell us which management skills were most important in your former occupation: recruiting? accounting? matchmaking? How did you choose among job applicants? Who were the best clients: rock stars, movie stars, studio execs, athletes, retired athletes?

[A] Fleiss: I didn't recruit. Girls came in droves, wanting to work for me. Sometimes I didn't know what to do, there were so many of them. Looks are an obvious head start. Also, you get vibes from the women who can do the work. Sometimes women thought they were tens and they weren't. Breaking the news was the hardest part. I never just came out and told them the truth. I would say, "I'm sorry, but I don't get requests for the sort of exotic beauty you have."

[A] The men never gave me money, they gave the women money, so I was probably ripped off all the time on my percentage. A typical client was a wealthy guy who didn't have the time to go out and meet a "decent" girl. I was able to come up with decent girls and wealthy guys, and introduce them. What they did from then on was strictly up to them. Maybe they had wild sex, maybe they had no sex. Maybe they got married, maybe they didn't. One out of 40 times my matchmaking was off. I was just able to get it right.

[A] I owned a nightclub with Victoria Sellers called On the Rox. We had parties. I'd meet a girl who, say, worked for a modeling agency. She'd take a trip for me, and afterward she'd tell a friend, "Guess what I did?" Instead of going, "Ooh, why'd you do that?" the friend would say, "Could I meet Heidi?" So all of a sudden—this is hypothetical, of course—I have 14 girls from a big modeling agency working for me. But it doesn't only go on there. It goes on at Beverly High and in Westlake.

[A] I personally slept with everyone in the occupations you mentioned [smiles], but as a group the girls preferred men from Fortune 500 companies. The real moneymakers, the people who could change the economy. Old money. The money that's not going to go away. That's also the type of man the women would fall in love with. Someone like Charlie Sheen, of course, the women would have fun fucking the hell out of him and his friends, all those other little actors, but they knew that's all it was. In terms of sexual prowess, I would have to say that Jack Nicholson is a goddamn great lover.

18.

[Q] Playboy: What's the worst time of the year in your former profession to take a vacation?

[A] Fleiss: One year I thought, OK, Ramadan is coming up, I think I'll go to Hawaii. Ramadan is when Arabs don't eat, don't sleep, don't drink, don't breathe for 30 days or something. So I expected things to be slow. But for some reason, it was so damn busy I couldn't leave. If it wasn't the Arabs, it was the studio execs. Someone was going absolutely crazy.

19.

[Q] Playboy: What's the fastest way to get a guy off?

[A] Fleiss: Since it's all mental, it's probably a combination of giving him head and talking dirty. But it has to be the right kind of dirty. You have to know what turns on a particular guy to hit those fantasies. Maybe a guy fantasizes about having another guy watch him have sex. Maybe he likes to hear about how many men his woman has fucked, so she tells him about a prince and his entourage. But he has to remember that it's all made up, so afterward he shouldn't disrespect her for it.

20.

[Q] Playboy: Tell us how to intensify the male orgasm.

[A] Fleiss: You need another participant no matter what. [Smiles] That's why phone sex isn't bigger than just phone sex. You absolutely still need that warm body next to you.

The former hollywood madam talks about hooking, hubris and what you can get for $40,000 a night