1. Aspasia
Aspasia was rocking the streets back when they weren’t really even streets. She ran one of the most hoppin’ brothels in Athens and strolling around with all its finest—even giving Pericles a lay now and then.
2. Russell Brand
Russell Brand is a man of many, uh… hats. He had that whole drug problem and he was (supposedly) also an escort occasionally to make ends meet. But look at him now! He married Katy Perry! For a while! And he’s super successful and funny. So it was totally worth it.
3. Calamity Jane
Calamity Jane wasn’t exactly trying to be a prostitute—at least not full-time. After all, she sorta looked like a dude. But anyway, when she wasn’t scouting and shooting Indians, which was what she was really known for, she made most of her bills sleepin’ with cowboys at Fort Laramie.
4. Sally Salisbury
Sally is probably the sassiest on this list (okay, well, second to Marilyn Monroe), known not just for shagging, but also stabbing a few people, and definitely contracting a few diseases along the way. She started her career in her early teens on the streets of eighteenth-century London, and she never looked back.
5. Marilyn Monroe
Marilyn ended up doing pretty well for herself—to say the least—but she didn’t exactly struggle to get to the top. She supposedly made about $500 a day “hanging out” with producers and directors, doing some porn as well as house calls. It’s hard to hold all that against her though. She was a good singer, after all.
6. Raquel Welch
Back when the dinosaurs still roamed the Earth, Raquel Welch was a little looser around the edges… according to her family. She apparently took Tijuana by storm back when she was Raquel Tejada.
7. Cora Pearl
Probably the classiest gal on the list, Cora was born in England in 1835 with much less than a silver spoon in her mouth. She pulled off a French education though, and she used her good looks and social grace to claw her way to the top… even if she had to dance naked and bathe naked in champagne a few times. Whatever.
8. Nell Gwyn
Prostitution ran in Nell’s family, but she put her “career” off for a few years and instead embarked into the magical world of theatre. Well, first she tried to sell fruits to make the rent, and would “give a little extra” for a tip. It worked out though—she caught King Charles II’s eye and became his mistress. Not bad.
9. Lulu White
Lulu was one of the staples of the New Orleans red light scene in the early 1900s. She wasn’t just a prostitute, she was an entrepreneur. She ran the most successful brothel in town, Mahogany Hall, and she only spent her nights with the most powerful men. Like a real dame.