America’s Most Notorious Pimps and Madams

Making money off the world’s oldest profession might just be the world’s oldest business. With profits ranging from 40% to nearly 100%, pimping’s money lures in all kinds of characters. Women, in fact, have become just as notorious as men in the business–just ask Heidi Fleiss.

Whether they’ve run with criminals, serviced politicians, or owned a famous brothel, the pimps and madams below have earned themselves a spot in US history.

Kristin Davis

Image: Kristin Davis

Eliot Spitzer probably did more for New York’s pimping and madaming scene than any politician in history. “Manhattan Madam” Kristin Davis claimed that Client No. 9 frequented her services, comprised of a total of three prostitution rings: Wicked Models, New York Body Miracle, and Maison de L’Amour.

Davis, a savvy businesswoman, earned millions through her high-end business, with hourly prices that went over $1,000. She collected client details in a massive black book that would make most other madams jealous. On the side, she built in enough leisure time to date baseball star Alex “A-Rod” Rodriguez.

After spending four months on Rikers Island for promoting prostitution, she came out and decided to focus on running for governor instead of doing the governor. She now represents the Anti-Prohibition Party. Though chances of her being elected are remote, it’s worth noting that she wouldn’t be the first madam to make it in politics.

Fillmore Slim

Clarence Sims started his career as a small-time blues musician. During a gig in Texas, he met his first hooker. Sims, seduced by the pimp lifestyle, moved to San Francisco and soon became the city’s “Pope of Pimping.”

Sims became Fillmore Slim, named for the San Francisco street where employed what he says were thousands of prostitutes.

After some hard knocks, Slim was eventually rediscovered as a blues musician, but not before making an appearance in the movie American Pimp, sealing his name in the annals of American pimpdom.

Xaviera Hollander

Hollander, otherwise known as the “Happy Hooker,” started out as the secretary to the Dutch and Belgian consuls, according to her biography, but became a call girl, when she needed more income. The attractive Hollander must have done okay, because she used her earnings to buy a retiring madam’s $10,000 list of clients.

Hollander penned her famous “Happy Hooker” book in 1971. In 1972, Hollander started writing “Call Me Madam,” a popular Penthouse sex advice column. Hollander, something of a Renaissance woman, now speaks, writes books, produces theater shows, owns a bed and breakfast, and enjoys an established public career as a sex expert.

Jason Itzler

The self-declared “King of All Pimps” was netting $25,000 per night at his NY Confidential brothel before the cops, on a bust inspired by none other than the New York District Attorney himself, shut him down in 2005.

Call it a minor setback. Once Itzler was released, he set up a matchmaking service called DNA Diamonds, which helps ultra-rich men find trophy women.

When the Feds caught former DA Eliot Spitzer with his figurative pants down, Itzler jumped into the spotlight claiming he was Spitzer call girl Ashley Dupre’s pimp. You still hear him pipe up on occasion, most recently claiming he supplied Tiger Woods with one of his many mistresses.

Sally Stanford

Image: Sally Stanford’s obituary/The Tiger is Dead

Mabel Busby, a.k.a. Sally Stanford, started her black-market career in the 1930s, as a bootlegger. She then invested her bootlegging earnings into the prostitution business, starting with individual prostitutes, then moving on to create some of San Francisco’s most elite bordellos.

In the 1950s, Stanford moved to the restaurant business, running Sausalito’s swanky Valhalla restaurant. In the 1970s, the former lady of ill repute became Sausalito’s mayor. She also survived 11 heart attacks and 5 marriages before passing away at the age of 78. Her famous quote, “us sinners never give up,” pretty much sums up her life.

Dennis Hof

“America’s Pimpmaster General” runs Nevada’s famous Moonlite Bunny Ranch brothel, which HBO featured in its Cathouse reality documentaries and series.

Hof keeps a high enough profile that he might as well also call himself “America’s PR Master General.” In 2008, student Natalie Dylan announced that she would auction off her virginity. The winner would be honored at none other than the Bunny Ranch. The act was never consummated, but Hof once again hit the spotlight.

More recently, Hof loudly campaigned to expand Nevada’s legal prostitution, presently legal only in rural areas, to Reno and Las Vegas. As is appropriate for a PR pimp, you can even follow him on Twitter.

Jessie Williams

Heard of the musical The Best Little Whorehouse in Texas? Well, that whorehouse was Texas’ Chicken Ranch, “perhaps the oldest continually running brothel in the nation,” according to THSA Online.

Its madam, Jessie Williams, started the brothel out of a house in 1905. Williams, who made a point of letting in politicians and “lawmen,” but keeping out criminals, upgraded to a new 11-acre location when her political grapevine warned her about an impending crackdown.

When the Great Depression hit her business hard, Williams “began the ‘poultry standard’ of charging ‘one chicken for one screw,’” writes THSA. The name Chicken Ranch stuck after that, for understandable reasons.

In the 1950s, Williams, no longer able to run the Chicken Ranch, passed ownership onto former prostitute Edna Milton. Texas Governor Dolph Briscoe closed the Chicken Ranch in 1973, but its name and founder’s story remain.

Bobbi Davis

You’re driving through Nevada, near Death Valley. You see a sign from the road: Shady Lady Ranch. You’re in the mood. You walk in and find a hot 25-year…gigolo named Markus?

Yes, you heard right. The Shady Lady, run by madame Bobbi Davis and her husband, hired America’s first legal “prostidude,” as the SF Examiner refers to him.

In terms of social progress, he compares himself to Rosa Parks. Though this might be a stretch, Bobbi Davis’ struggle to license Markus in turn put the Shady Lady on the map. Markus has since been replaced with a stud named “Y.Not.”

Iceberg Slim

Iceberg Slim, or Robert Beck, or “America’s Pimp Laureate,” “credits his mother for having prepared him for the pimp lifestyle by pampering him during his childhood,” according to the Biography Project. Take note, pampered sons, because you, like Iceberg Slim, could spend nearly a quarter century as a full-time Chicago pimp.

The jail time afterwards may not be as easy, though. Nor would writing a smashingly successful autobiography like “Pimp: The Story of My Life,” becoming a Black Power icon, and having a movie made out your book.

Iceberg Slim probably also wrote the best pimp dictionary of all time, located in his book. It includes words like “bottom woman” and “chili pimp.” I’ll leave the definitions to you.

Deborah Jean Palfrey

“D.C. Madam” Deborah Jean Palfrey ran the $2 million, 130-employee Pamela Martin and Associates escort company between 1993-2006.

The madam, who ironically studied criminal justice in college, failed to make it big with her first escort business because she was arrested. A year and a half in jail gave her time to refocus her efforts. Once released, she created the successful agency that lured DC’s hungry men with $300/hour prostitutes. It later came out that clients included Senator David Vitter and Washington Times columnist Harlan Ullman.

After the Feds caught up with her for tax evasion, Palfrey hung herself to avoid her long prison sentence. Now, there’s a book out about how Palfrey was actually lynched by the cops and the media.

Polly Adler

Polly Adler published an autobiography a few years before her death.

New York City madam Polly Adler had the protection of prominent Mafiosos, including Lucky Luciano, when she opened her first brothel in the 1920s. During the course of her reign, Adler ran a total of nine brothels in the city. She counted mobsters, businessmen, and even the mayor as clients at her plush establishments, which included perks like card games and alcohol.

Although the cops were always after her—for kickbacks, as they were corrupt at the time—Adler burned out from madaming rather than being burned by the law. Along with Kristin Davis and 1980s “Mayflower Madam” Sidney Biddle Barrows, Adler has a place in history as one of the city’s most notorious madams.

Joe Conforte

Former taxi driver Joe Conforte and his wife bought Nevada’s Mustang Ranch in the late 1960s. In 1971, thanks in part, to Conforte’s lobbying efforts, it became the Nevada’s first legal brothel.

Staying legal, however, wasn’t Conforte’s forte. When he wasn’t trying to avoid taxes, bribe or buddy up with politicians, he was exploring other ways to bring in the mighty dollar.

He and his business parter-cum-wife, Sally, decided to promote heavyweight boxing champ Oscar Bonavena, according to this CNBC article. Bonavena developed a crush on Sally, then announced that he wanted to take over Mustang Ranch.

Joe, furious, told Bonavena never to set foot on Bunny Ranch again. When Bonavena appeared at the Ranch anyway, somebody shot him dead. A security guard took the blame, but the Confortes still weren’t that far ahead of the law.

In 1977, the IRS busted them for owing around $18 million in taxes. In 1990, after legal delays, the IRS seized the property, auctioned it, and sold it to a dummy company—headed by Joe Conforte.

Instead of ‘fessing up, the Confortes took off to Brazil, from which they couldn’t be extradited. In 1999, after pursuing the Confortes in court, the Feds shut down Mustang Ranch; it has since been reinvented by another couple.

Heidi Fleiss

Image: Daniel Dacumos

“Hollywood Madam” Heidi Fleiss managed her first prostitution ring at the tender age of 23, under the not-so-soft tutelage of “Madam 90210” Alex Adams, who took care of Beverly Hills’ needs through the 1980s. (Adams later referred to Fleiss as a “Jewish-American Princess,” probably out of jealousy of her protégé’s success.)

After managing Adams’ business for a while, Fleiss branched out on her own, using money and connections she’d gained during a relationship with 61-year-old elite financier Bernie Cornfield. Rich and famous men would call Fleiss, tell her where they’d be traveling and when, and Fleiss would set them up with the kind of company they wanted. The savvy Fleiss would earn 40% of each transaction.

After an LAPD sting put Fleiss in prison for 3 years, she gave up the madam life for other businesses, including a clothing line, a sex tape, a Laundromat and an appearance on Celebrity Big Brother. She came full circle, in a way, by becoming engaged to fellow pimp-type Dennis Hof in 2009.


John Dickson, more commonly known as Rosebudd, might just exemplify the 1970s pimp that we’re so fond of theming parties after.

The “American Pimp” star became famous not only as the movie’s centerpiece, but as someone who brought the pimping world closer to the viewing masses. He explained, for example, why he didn’t give his “hos” a cut of their earnings—and why that’s not exploitation.

The “Master of Pimpology” more recently published a book on his pimp life. He has retired to more mellow things, like running a tattoo parlor. His American Pimp costar Bishop Don “Magic” Juan also retired from pimpdom, ending up instead as a man of God. Not everyone can keep pimping into their golden years, it seems.

Honorable mention: Hugh Hefner

Image: Glenn Francis,

Although the Playboy founder never prostituted anyone that we know of, we had to mention him for his symbolic status as a cool cat, a man about town, a guy with three women on his arm. He’s one of the world’s few 84-year-olds who men still want to be, and women still want to be with. Now that’s a pimp.

Written by Drea Knufken

Currently, I create and execute content- and PR strategies for clients, including thought leadership and messaging. I also ghostwrite and produce press releases, white papers, case studies and other collateral.