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The Greatest Tarts in New York History

An Illustrated Guide

Kristin Davis (1976–)

New York's latest famous tart is most likely destined to be a footnote to the Eliot Spitzer scandal, but the enthusiasm with which madam Kristin Davis rode Ashley Dupré's coattails to her own hooker fame is certainly charming. She also scores points for the amusingly (and yet somehow not) vague names of the three prostitution rings that led to her arrest: Wicked Models, Maison de l'Amour, and New York Body Miracle. And then there's this: Davis is about as close as you can get to looking like Amanda Lepore without actually being born a man.

Photograph: nypost.com

Ashley Alexandra Dupré (1985–)

If Bon Jovi wrote a song about a tough but sweet Jersey girl chasing a New York dream, that song would star Ashley Alexandra Dupré. Born Ashley Youmans, Dupré moved to New York at 19 to be a singer but wound up working for the Emperors Club prostitution ring as “Kristen” (it happens). Eventually this led her to the Mayflower Hotel on February 13—and you know the rest. But Ashley’s not letting go of those little-girl dreams: She put a few of her own pop songs online when the story broke, making more than $200,000 as of mid-March.

Photograph: myspace.com

Samantha Jones (1998–)

She's fictional, but so many New York women have so consciously embodied the Sex and the City aesthetic that Jones's influence might be greater than anyone else's on this list. Of the four ladies of SATC, she was the proud strumpet: As she rarely slept with the same man twice, her exploits are too numerous to list but, we can confidently say, included anything (legal) you can think of. And in a case of life imitating art, Kim Cattrall—the actress who plays Jones— has written two sex books herself.

Photograph: Courtesy of New Line Cinema

Amy Fisher (1974–)

Maybe the youngest—and most dangerous—of all our tarts, Fisher spent seven years in jail for the attempted murder of the wife of Joey Buttafuoco in 1992, with whom she had been having an affair since she was 16 years old. Upon her release, Fisher grew into her strumpet-y shoes: She reunited with Buttafuoco for the coin toss at the 2006 Lingerie Bowl, and in October of 2007, news of her sex tape hit the Internet—it reveals signs of breast augmentation. Girl’s been busy since the slammer.

Photograph: Getty Images

Madonna (1958–)

Does this need any explanation? Madge was born and raised in the Detroit suburbs, sure, but she made her name in New York City—and how do you suppose she did that? Talent and perseverance? Yes. Awesome fingerless lace gloves? Yes. Dry-humping a four-poster bed while wearing said gloves? Oh yes. Relentless reinvention of said dry-humping for the next two decades? Hell yes.

Photograph: Getty Images

Megan Marshak (1953–)

Nelson Rockefeller died of a heart attack in 1979 while having sexual intercourse, and underneath him at the time was his 26-year-old aide, Megan Marshak. But rather than call the authorities immediately, Marshak called a friend, and she had the brass ones to pick up the phone and call 911. Marshak has never commented on the circumstances of that night, but her talents speak for themselves.

Photograph: AP

Sidney Biddle Barrows (1952–)

Barrows ran Cachet escort service from 1979 to 1984 and, during that time, catered to only the best: sheikhs, executives, diplomats. After all, she was a scion of Philadelphia’s upper-class Biddle family and a Mayflower descendent—she’s not messing around with cheap stuff. After being shut down in 1984 and pleading guilty to charges, she wrote the best-selling memoir Mayflower Madam, which was optioned into a TV movie starring Candice Bergen. Live the dream, lady.

Photograph: Getty Images

Bess Meyerson (1920–)

The first Jewish woman to win the wholesome Miss America pageant in 1945, Meyerson later became known as Ed Koch’s frequent walker companion during his 1977 campaign for mayor. She became a scandalous strumpet in the late eighties with what was known as the Bess Mess: her affair with millionaire tax cheat Carl Capasso, who then got divorced—and who later bribed a State Supreme Court justice to lighten up the alimony. To grease the wheels, Meyerson hooked up the justice’s daughter with a job. Indictments for everyone!

Photograph: AP

Xaveria Hollander (1943–)

Famous for her book The Happy Hooker: My Own Story, Hollander quit her job at the Dutch consulate in Manhattan in 1968 to become a $1,000-per-night call girl (wonder if that price would hold today with inflation?). A year later she went into business for herself as a madam, opening the subtly named Vertical Whorehouse brothel. She soon became a trampy superpower— until she was shut down in 1971. Now she runs a bed-and-breakfast in Amsterdam that caters to all of your nonsexual desires.

Photograph: Getty Images

Valerie Solanas (1936–1988)

She's best known as a radical feminist who attempted to assassinate Warhol (the movie I Shot Andy Warhol was about her), so why is she included on this list? First of all, Solanas is rumored to have supported herself in her itinerant, pre-Factory years as a prostitute. And more important, legend has it that in 1967 Warhol refused to produce Solanas's play Up Your Ass because even he found it too pornographic. An assassin-feminist-prostie who reclaims porn? Welcome, Valerie.

Photograph: AP

Gypsy Rose Lee (1911–1970)

When most burlesque dancers and prehistoric strippers were awkwardly ripping off their garters, Gypsy Rose Lee was making a name for herself at Minsky’s Burlesque with her casual, witty send-up of the striptease. She owned the stage there for about four years, where she was often arrested in police raids; eventually Lee went on to make a few Hollywood films, sleep with some men of import, and write a memoir that earned her the devotion of theatergoing gay men the world over.

Photograph: Getty Images

Polly Adler (1900–1962)

She was the American dream: A Russian immigrant who lived in complete poverty before opening her first bordello in 1920, Adler reigned as New York's most famous madam and a society fixture for 25 years. (Like Kathy Hilton, kind of, if Kathy were wittier and had lots and lots of Parises). Her brothels serviced cops and gangsters, writers and politicians, while Adler traded witticisms with Robert Benchley and Dorothy Parker. Makes us long for the good ol' days.

Photograph: AP