The Rise and Fall of Heidi Fleiss, Hollywood's Most Notorious Madam

When it comes to society's attitudes toward sexual expression, the 1990s were a formative time in American culture. David Friend's fantastic and wonderfully exhaustive new book, The Naughty Nineties, takes a deep, deep dive into everything sex when it comes to 90s American culture—from Baywatch and Bill Clinton to Sex and the City and the proliferation of digital smut. Today, we're sharing an excerpt from Friend's book—specifically focusing on notorious Hollywood madam Heidi Fleiss and her fascinating rise (and fall) in the public eye.

"Lookit—my life," she says. "I've had tremendous highs. I spent one evening with Princess Diana. I've had dinner with Nancy Reagan. I also spent [part of] 1997 in solitary confinement in the penitentiary in Dublin, California."

I am at the desert hacienda of Heidi Fleiss. My host gained national notoriety after her high-profile arrest in 1993 on charges connected with running LA's toniest prostitution ring. She would become widely known as the "Hollywood Madam." People magazine would refer to her as the "sex broker to the stars." Kid Rock would sing about her ("Start an escort service… find Heidi Fleiss."). Indeed, her operation had been such a sine qua non in the sin cycles of many of the world's power brokers that on any given night she would have "Heidi girls" on at least three continents and not infrequently aboard a private or corporate jet.

Chez Fleiss—surrounded by cacti, brush, and desolation—is located in a frontier town named Pahrump, Nevada. It consists of two trailers, which have been converted into a spacious ranch house. To get here, I have driven an hour along the parched perimeter of Death Valley without spying a human soul. And then, like some portent out of Castaneda, I see a vision. A titty bar. And its adjoining billboard announces her: "Ex–Hollywood Madam Heidi Fleiss book 'Pandering' autographed and sold at the Kingdom, All Nude Gentlemen's Club." Tempting, yes; but I decide to drive on to my destination.

Fleiss's property, on the barren outskirts of Pahrump, finally appears, up a winding dirt road. New signs await me: "Do Not Enter," "Keep Out." I park and Heidi Fleiss emerges with a macaw on her shoulder. "It's my Robinson Crusoe house," she says playfully as she greets me. She ushers me inside for Perrier. I notice macaws and exotic birds of every color—I count twenty—on perches and ledges. I also spot splotches on the floor.

Fleiss shows little hint of her sleek former glory. She looks wan, her facial features sunken. She has recently gotten off crystal meth—"the white trash drug," she tells me. She has completed a stint on TV's Celebrity Rehab with Dr. Drew. (The public humiliation, she claims, was actually therapeutic.)

Indeed, she has reality TV in her blood. Mike Fleiss, a cousin, is one of the giants of the genre, having produced the breakout successes Who Wants to Marry a Multi-­Millionaire?, The Bachelor, and The Bachelorette. Heidi, too, has appeared on a string of such programs ( Celebrity Big Brother, Sober House, even Animal Planet's Heidi Fleiss: Prostitutes to Parrots). She is a woman straddling two cognitively dissonant lives: one tethered to the here and now, one pure façade; one steeped in addiction and criminality, one in sexual fantasy.

Then again, she is funny and whip-smart. Her opinions spew out in burbles. She is cocky and coquettish, though painfully self-conscious. She is also darkly transfixing, with an almost lupine spirit. "Charles Manson was captured a half hour from here," she says, as if to spook me.

Today, Heidi Fleiss is wearing gray Superbad sweatpants, house slippers lined in fluffy pink, and a blue sweatshirt speckled with macaw caca. Her two housekeepers, she explains, have "up and quit" two days before. She acknowledges her current state with a bright pop of self-deprecation: "I'm in my sweats cleaning up bird shit." But she is sanguine nonetheless. "My life [is] finally balanced out right now. Sure, it is a very unconventional and dysfunctional lifestyle I have, living with these birds. But, somehow, I make it work."

Initially, Fleiss had moved to Nevada (where prostitution is licensed and legal in certain counties) hoping to open an all-male brothel catering to women. But "Heidi's Stud Farm" went off the rails when she came up against local resistance, some legal issues, and, oddly, a new preoccupation. Fleiss, it turns out, had befriended Marianne Erikson, a neighbor who was elderly and bedridden. An ex-madam, Erikson used to run the exotic bird department at the Tropicana Hotel in Vegas, and upon retiring maintained a menagerie in her home trailer. "I would go and visit her," Fleiss recalls. "She had all her birds in cages with these big Frankenstein bolts, and the birds would be
screaming and rattling the bolts."

In 2006, as Erikson lay dying, Fleiss called the paramedics. "Her last words were, 'You take care of my birds.' I told her, 'No.' But this is where I am. I fell in love with these birds and I lost interest in the sex business. …I'll never turn my back on them." Most nights, she says, she is alone in this place on the edge of the desert. "In the evenings, they fly around here. I don't clip their wings….I don't keep them in cages."

I am introduced to Paulina, Paul, Rodin, Freddie, and Simon. Golly used to work in a furniture store and likes to declare, "Half-off!" Suzy speaks Spanish; two others speak Mandarin. Reggie, Heidi insists, is gay. She describes his habit of pecking at another male, occasionally finding him in dirty-bird flagrante: "He turns him upside-down, sixty-nines him." Now and again, her feathered friends break into conversation, their calls suggesting a sort of cacophonous Greek chorus.

Between 1991 and 1993, Heidi Fleiss ran a ring of high-end call girls, some five hundred at one time or another. They charged upwards of $1,500 a night. (Fleiss says she pocketed 40 percent.) Clients ranged from Fortune 500 execs to dissolute young heirs and royals, from rock icons to the free-spending studs at the studios. The typical Heidi "type," she explains, "look[ed] clean-cut and perfect….I want[ed] a guy to know that she was born and raised in Beverly Hills, stepped off the cover of Seventeen magazine, but she's going to fuck like Jenna Jameson in the bedroom. She's going to be the nastiest girl on the planet. She's going to bring in other girls—do this, do that, do things you never even heard of. That's the girl."

Even so, Fleiss maintains, the sex itself was never hyper-kinky. "At the levels and money I'm dealing with," she says, "there is no time for anything like that—where people are going to [try] asphyxiation and die. There was nothing so abusive or so degrading that someone was going to, the next day, feel shameful or hurt….If drugs and drinking [are] involved, there's, like, people you don't expect, all of a sudden, will want to suck a dick or whatever….That kind of thing wasn't as weird as you thought. [Or] all of a sudden you want anal sex—a tennis racquet, but which end? Stuff like that… Okay, yeah, you'd never understand that this billionaire wants to wear lingerie. But so what?"

Her heyday, like the mayfly's, was brief. In her early twenties, she started turning tricks for the legendary Madam Alex. "I wish I was a better hooker," she laughs. "I couldn't compete with the other girls." She soon realized that her aptitude was not in servicing clients but in the service business. Before long she was running the show, then setting off on her own, and for two or
three heady years, she had cornered L.A.'s top-tier sex trade.

Her original objective, she says, had been to make enough capital to switch careers (possibly to real estate), a dream of many a young entrepreneur. But she got hooked on the glamour, the octane, and the power. She fell in, she says, with "people who are 1 percent of the wealthiest in the world….I remember when one client paid me $10,000 in $500 bills. A palette of silver bars showed up at the house [one day] that weighed like seven pounds each. I used to use them as doorstops…. I had one girl on the cover of Seventeen magazine, Harper's Bazaar—all working for me."

She recalls dispatching her troops to the Clinton inaugural in 1993; to Argentina, for polo season; to yachts in Acapulco and Monte Carlo. She had four phone lines at her house in Benedict Canyon; lovelies lounging by the pool; drugs aplenty. At her trial, a real estate grandee described shuttling
Fleiss's damsels on his private plane. Even heads of state, she bragged, would phone her directly. "If I really came out and talked," she told Lynn Hirschberg in Vanity Fair, "I could have stopped NAFTA."

Today, Fleiss speaks with astonished wonderment. "It seems like another world ago. I was living in a world that was really not realistic. I mean, not too many twenty-five-year-olds go and buy a [multi]million-dollar house up in Beverly Hills like that and just live that lifestyle….My neighbors were Bruce Springsteen, Bernie Brillstein, Jay Leno, and Jack Lemmon."

She shifts from past to present tense, as if reliving the rush. "It just keeps getting better and better, like the wave is never going to crash. I remember some days—I hate to put it [in] financial [terms]—I'd be, like, 'Okay, let's see if I can make $200,000 by the end of this week.' And I'd be, 'Oh my God, I made $300,000.'…Like you get in a zone….Everything was fun. I mean, girls are getting paid to fuck Charlie Sheen."

And the parties. "They didn't have sex for money at my house, but they would come hang out. It was social….You've got people like Jack Nicholson and Mick Jagger partying at your house"—not to imply that any of these guests partook of her stable's services. "I remember coming home and Prince was dancing in my living room."

Surely there had been flesh-peddlers who catered to the elite. But Fleiss was a new, '90s breed. She was in her twenties. She was hardly inconspicuous, driving around town in a '92 Corvette or a '67 Mustang. And she personified call-girl chic at a time when hookers were in sudden favor—in films like Pretty Woman, in fashion, in rap. Just months after making bail, she started a casual clothing line—Heidi Ware. She entertained offers for movies-of-the-week. She granted interviews. She posed in her Vette (in black boots and her signature shades) for Annie Leibovitz. She wore Norma Kamali and Dolce & Gabbana to the courthouse, and her state trial drew the likes of columnist Dominick Dunne and Sydney Biddle Barrows (the Mayflower Madam, dressed in Chanel).

She stood out in another way too. In her insular sisterhood, discretion had always been the watchword. But Fleiss was a slave to her addictions—and her ego. And she would eventually see it all implode because she was, at twenty-seven, a woman of her times: a chatterbox in an era of braggadocio.

In December 1992, she crowed to the Los Angeles Times, "Look, I know Madam Alex was great at what she did, but it's like this: What took her years to build, I built in one. The high end is the high end, and no one has a higher end than me….In this business, no one steals clients. There's just
better service." Her gloating immediately put the LAPD on her tail. (She would eventually be jailed on federal charges of evading taxes and laundering money.)

"I sunk my ship—I did," she now allows, blaming no one but herself. "I was an idiot. And I have to take responsibility….We all knew what we were doing. The girls knew it was illegal. The guys knew it was illegal. I knew it was illegal. I didn't think I'd end up in…a federal prison. For sex? But [that's what happened]. They can say it was [for tax charges by] the IRS. There's nothing else to it but sex."

Fleiss went down fighting. She struck back when her black book was fought over by the law and the press. (The "black book," she tells me, consisted of a few red-bound Gucci day planners.) She lashed out when former lovers or members of her aviary tried to feather their nests by dangling secrets (interviews, audiotaped phone calls, incriminating videos) in front of the tabs and tabloid TV.

The main reason for her overnight celebrity? Her flock serviced celebrities. And if anyone personified flagrant sexual indulgence in the '90s it was her client Charlie Sheen. In video testimony at Fleiss's trial, the actor admitted that in a year's time he'd spent $53,000—two dozen occasions' worth—for Heidi-caliber companionship. (Though Sheen had ridden an '80s wave to stardom in movies like Platoon and Wall Street, he became a '90s caricature of self-destructive behavior.

Known, as he once put it, for "banging seven-gram rocks," Sheen told Maxim that by the year 2000 he'd bedded some five thousand partners. Fifteen years later, he would announce he was HIV-positive.) "He's the most well-known client [of mine]," Fleiss says, "because his traveler's checks were in my purse…when I was arrested. [Otherwise] there was no reason to give him up….I had people who spent a lot-­lot more money with me."

Comparable offenders might have managed to get off lightly. But Heidi Fleiss had no such luck. She would serve three years, hard-core. And she survived it, she concedes, by adapting to her environment. Of prison, she reports, "It's lesbian hell. I had a girlfriend"—an airplane mechanic, she says, who was in on drug charges. "[Now] she has a huge company that's worth a few million dollars." Her second lover "looked like J-Lo. Men are my preference, but you're there, and you just do what you're going to do."

Her takeaway from the decade, she says—as a woman running her own business, as a sexual creature, and as a strong-willed individual—is that the era gave females new command over sex and power. "The world has changed with women and independence and money. [During] the '90s, I was living with Victoria Sellers in my house in Beverly Hills and [we'd] say stuff like this: 'Do you want a blonde or a brunette tonight?' A blond or a brunet guy. I'd go, 'I don't care, as long as they don't call me back. I have work to do in the morning.' It just became a thing, I think, where women didn't feel so pressured that they have to marry the first guy that they have sex with. I don't know if [the attitude was more] casual—or realistic."

Men, she contends, cannot not sleep around. "Men will fuck mud," as she puts it. But in the '80s and '90s, she says, women became more pragmatic about the interpersonal hypocrisy that had previously been a largely male preserve. "Women [became more] confident. A woman felt, 'I can act on my impulse.' " She attributes much of this brave new sense of authority and self-possession to a single role model. "Madonna has a lot to do with everything. From 'Like a Virgin,' all her songs—I think Madonna is a catalyst, an incredible force of nature, [teaching] women, 'Be yourself' and 'Do what you want to do' and 'Express yourself.' "

Fleiss turns reflective. "I have very low self-esteem….I listen to everyone. But [in the end] I'm going to make my own decision, no matter what….My image is: I'm associated with something bad—illegal, prison. So I have a different kind of stigma attached. I'm aware of it and it doesn't bother me. Look, I don't care what people think. If you care what people think or say—you're a prisoner. Your life is over."

Now that the dazzle and the crime and the punishment are behind her, I ask, what lasting mark did she make, in the end, on the decade and the culture?

She says she managed to relieve some pressure on the American conscience—on millions who were struggling with their angst and qualms surrounding infidelity. "Everyone has something," she figures, "a little bit of scandal. Everyone really does. It's just whether you find out about it or not. It's human nature. You cannot help yourself. In the '90s, when people found out about what I was doing with my operation, it made everyone breathe a little bit easier: 'Phew, it's not only me.' They didn't feel they had a dirty little secret. All men will cheat. Women too."

Moreover, her own scandal, she believes, helped create and define a market for exposing the dirtiest secrets of public personalities—for better and for worse. "It was the time that Hard Copy, Inside Edition, and A Current Affair were exploding. They were so hardcore gossip. And so I was plastered on all of that. Everyone wants to be famous. So anyone could make an accusation about me. And many people did—and got paid for it. Some were true and some weren't true. I don't really care now—I can only laugh about it." But, looking back, she says, she sees herself as something of a tabloid trial balloon. "It was a weird celebrity time. My situation was on the cusp of that tabloid explosion. I went to prison from 1997 to the millennium. And that's when the Internet came. Paris Hilton. The Bachelor—which my cousin owned….A lot of this reality stuff is based on whatever went down with my arrest—and the tabloid culture of the era, which I'm not too proud of. I [helped] spawn this brain-dead television thing."

"Movie star," Gina, a scarlet macaw, cries out, as if listening in.

"I love Gina," Heidi says, shaking her head. "I just don't know how I wound up here. In Death Valley. With twenty macaws. I just don't know."

From the book THE NAUGHTY NINETIES. Copyright 2017 by David Friend. Reprinted by permission of Twelve/Hachette Book Group, New York, NY. All rights reserved.