Where the ‘Hollywood Madam’ Heidi Fleiss Is Now

In the new Netflix documentary, aka Charlie Sheen, Heidi Fleiss — who became known as the “Hollywood Madam” when she was arrested in 1993 — reflected on how she ended up in the business of sex and found so much success. 

“I’m born and raised in L.A.,” she said. “Everything was the perfect storm to make me the perfect madam. I was young. I was arrogant. I was the best.”

Later, the now-59-year-old asked herself, “How did I f— up the best job on earth?”

In the ‘90s, Fleiss’ “little black book,” which allegedly contained the secrets of her prostitution ring, made major headlines as people in Hollywood and around the world wondered who had used her services — and if she would start naming clients. However, only one client was ever revealed: Charlie Sheen.

The Two and a Half Men actor opened up about what went down in both his documentary and his new memoir, The Book of Sheen. 

How Heidi Fleiss ended up in the sex world — and under arrest

Fleiss was born in Los Angeles on Dec. 30, 1965. She was one of six kids, and her father was a pediatrician who ended up with major celebrity clients. Fleiss ”liked to be out there, admired. She wants to be the rock star,” a source told PEOPLE in our 1993 cover story about the drama.

Fleiss’ road to the world of sex work began when she was dating Ivan Nagy, a Hungarian director who was 27 years her junior. Madam Alex — another famed Hollywood madam whose real name was Elizabeth Adams — claimed to PEOPLE that Nagy sold Fleiss to her to pay off a $450 gambling debt. Nagy, however, who died in 2015, told PEOPLE that Adams was “a very evil woman.”

Fleiss, for her part, said Nagy received money for introducing her to Adams, but added of the madam, “There’s not one redeeming quality to her,” accusing her of being “jealous.” 

Adams, who died in 1995, explained to PEOPLE, ”I was fond of Heidi. But she has a streak that’s so vindictive.” Either way, Fleiss learned the business at Adams’ side and then took her contacts to start on her own. 

William Stadiem, a writer who was working on a memoir with Madam Alex, explained in 1993 that in Hollywood, sex work “was really a low-key, secret profession.” But Fleiss didn’t go to great lengths to conceal what she was doing. One of her former employees told PEOPLE, “The other madams don’t hang out with the stars. Heidi’s young and cool, and she can hang out.”

Los Angeles police captain Capt. Glenn Ackerman said the department went after her operation because of “her own big mouth.” In 1993, Fleiss was the subject of a sting operation, and when she brought her employees to a set meeting spot, she was arrested. Ackerman claimed, ”She told us that we should have better things to do than arresting a poor little party girl. She said we ought to be out arresting real criminals, not her.”

The police admitted that her “little black book” was just a list of names, and that unless she gave them the context of what the people in it actually did, they couldn’t make any definitive claims. But then they found checks from Sheen.

Charlie Sheen confessed to the police

Sheen, 60, writes in The Book of Sheen that he never felt “dastardly or corrupt” buying sex. He considered the payment “a convenience-tax for a guaranteed outcome the other dating scenarios couldn’t offer.”

He writes, “The women were never misdescribed or falsely represented with their age or personalities. Heidi knew the value of customer trust, and she built on that with her consistency. What most people don’t understand is if you took the financial component out of the equation, the women were just as classy as the terrific gals I’d meet at clubs, bars and parties.”

Then, one day, Sheen paid Fleiss using traveler’s checks. “I was fresh out [of cash] and thought it ‘coke-wise’ to use my checking account to settle my tab with Heidi,” he writes. When Fleiss was arrested, he realized the checks were his “only link” to her. He would ultimately admit to giving her over $53,500. 

When the feds spoke to Sheen, they told him he could face five years in jail for “pandering” because he bought sexual services for his friends. He claimed in aka Charlie Sheen that he would have taken the misdemeanor, but not the pandering charge, which was why he agreed to testify in exchange for immunity. He taped his testimony with Fleiss in the room and said he could see her feelings of “betrayal and sadness.”

Sheen said in the doc that he regrets it, noting, “Snitch is not a color I wear well.” He and Fleiss have not spoken since.

In the doc, Fleiss made it clear she doesn’t forgive him. “I wouldn’t have said anything. I’ve never said anything about anyone,” she said about keeping her clients’ secrets. Of Sheen, she said, “He’s a crybaby rich boy. He’s a rich kid from Malibu. They’re not gonna do s— to him. He’s Charlie Sheen. He was at his peak then. They’re not gonna do anything to him. Are you kidding me?”

Heidi Fleiss’ life after the trial

Fleiss was ultimately convicted of tax evasion in 1996 and sentenced to seven years in prison. She served 20 months at a federal facility and was then released to a halfway house in November 1998. 

In 2004, Fleiss told PEOPLE she was planning on opening a brothel for women near Las Vegas and had moved to Nevada. “It’s going to be called Heidi Fleiss’s Paradise,” she said. “I know this business better than anyone. I know what people want. It’s my one area of expertise.” She eventually abandoned those plans.

In 2003, then-boyfriend Tom Sizemore was arrested for domestic violence. The actor, who died in 2023, was sentenced to six months in prison. She and Sizemore both appeared on season 3 of Celebrity Rehab with Dr. Drew, filmed in 2009.

Fleiss settled in Pahrump, Nev., where she spends her time rescuing macaws. “I don’t care about people having sex now. I’ve been there and done that,” she told PEOPLE in December 2024. 

Explaining her passion for freeing and caring for parrots, she said, “These birds have no other option other than to live in a cage, die in a cage. Once I realized this problem existed, I couldn’t continue living my life without doing something about it.” She said she was inspired, in part, by her own experience living “in a cage” in prison.

“I’ve made mistakes, but I don’t mind a hurdle,” she said of her past. 

Aubrey Plaza is set to play Fleiss in a new film, The Heidi Fleiss Story. “I just think she’s an incredible person, incredible character,” she told IndieWire in August. “The story is insane,” she said, adding that Fleiss is “the ultimate bada– icon and she deserves the royal treatment.”