The Top 10 Best Movie Sex Workers

5. Vanessa- Deadpool and Deadpool 2

Before she was in a committed relationship with the Merc with the Mouth (Ryan Reynolds), Vanessa (Morena Baccarin) “bumped fuzzies for money.” In fact, that’s how the two first met. See, Wade had a wad of cash to blow after a big job, and Vanessa saw an opportunity to make rent for the month. The two didn’t realize that night of exchanging sex for cash (along with a yogurt card and a Voltron Defender of the Universe Ring) would be the beginning of a beautiful relationship. Despite breaking the number one rule for movie sex workers, Vanessa deserves a spot on this list because she is legitimately a wonderful woman who finds a healthy, loving relationship with another weirdo like her. Some people think that Joker and Harley Quinn are the ultimate comic book couple, but I’m team Vanessa and Wade. She’s funny, smart, confident, and beautiful, making her the kind of escort that makes you wonder if prostitutes accept credit cards.  

4. Gail- Sin City and Sin City: A Dame to Kill For

Not all movie sex workers are victims of the industry. In fact, Rosario Dawson’s Gail runs the industry in Sin City and rules the city’s red-light district with an iron fist. Her merry band of sex workers roams the streets packing heat and taking care of their own. They even have their own ninja-samurai enforcer who quickly takes care of any guys who think they can rough up the ladies of Old Town. Not even cops dare enter “Old Town” without Gail’s permission, and she’s not exactly on good terms with them. Dawson is no stranger to comic book roles, but Gail is definitely her most iconic with the colorful costumes, femme fatal sex appeal, and trigger-happy attitude. She’s earning a high spot on this list of cinematic sex workers because she organized her fellow streetwalkers into urban Amazons that keep their turf the safest in the city. She’s easily the most badass character here.     

3. Ophelia- Trading Places

One of the biggest tropes in Hollywood is the hooker with a heart of gold character. Well, no one else on this list embodies that description quite like Ophelia (Jamie Lee Curtis). Louis Winthorpe III (Dan Akroyd) finds himself destitute and homeless thanks to a bet made by his insane bosses to swap his life with a smooth talking conman, and all his former friends turn their backs on him. Despite being a pretty smart guy, Louis is an idiot when it comes to street smarts. Luckily, he runs across Ophelia who can’t bring herself to let the guy freeze on the streets over Christmas. She takes him in and helps him get back on his feet, even though he’s a bit of a pain in the ass. Hell, she even helps Louis exact his revenge on his former bosses. Ophelia’s life as a streetwalker wasn’t glamorous, but she proved that sometimes those who have had the roughest lives have the biggest hearts, making her one of my favorite movie sex workers of all time. 

2. Vivian Ward- Pretty Woman

Some people have called Pretty Woman a reimagining of the classic Cinderella story, which is a little disturbing if you really stop and think about it. However, there’s no arguing that it isn’t a 90sclassic. When corporate raider Edward Lewis (Richard Gere) needs a bit of arm candy, he turns to Hollywood Blvd hooker Vivian Ward (Julia Roberts) to escort full time for the week. In his mind, a professional means all the benefits of a relationship with none of the commitment. Vivian surprises him when she defies his preconceived notions of sex workers. Over the course of the week, she charms her way into his heart and helps make him into a better man. As I mentioned, the number one rule of sex work is to never fall in love with the client. Well, the same can be said for the clients as well, because Edward goes and falls in love with Vivian. When it comes to movie sex workers, it’s hard not to have a bit of a crush on this iconic character.  

1. Sera- Leaving Las Vegas

I don’t mean to get all philosophical, but it seems to me that one of the main reasons people employ sex workers is because they want to be accepted for who they are. That’s why I have to give the number one spot on this list to Sera (Elisabeth Shue) from Leaving Las Vegas. She has quite the week when a suicidal author (Nicolas Cage) hires her to assist him in drinking himself to death. Basically, all she has to do is hang out with him, be his designated driver, keep feeding him booze, and make sure emergency services don’t resuscitate him when he dies. The only rule is that she can’t judge him for his drinking, and he won’t judge her for her profession. At first everything goes to plan, but Sera starts to feel for the guy and can’t let him go through with it. The choice isn’t hers to make though, and in the end she has to accept him for who he is in order to love him in his final moments. Shue earned an Oscar nomination for her performance in this gut-wrenching tragedy.   

Honorable Mention: Mona Stangley- The Best Little Whorehouse in Texas 

Look, I’m not going to try to say that The Best Little Whorehouse in Texas is a great movie by any stretch of the imagination, but Dolly Parton is a national treasure, and there’s just something that feels right about her in the role of a kindly matriarchal madame of a Texas bordello. Old Mona has a pretty solid operation going thanks to her “intimate relationship” with local law enforcement, and they’re happy to look the other way when it comes to the whole sex-for-money thing. While the film might not be great, Parton is delightful even in the worst movies, and I figured she deserved an honorable mention based on her natural charisma alone.   

Shout-Out: Elizabeth Shelley- Frankenhooker 

There is a movie out there called Frankenhooker and it is just as incredible as it sounds. It is quite literally the tale of Frankenstein but with a prostitute instead of, well, a creature. How could I not do a list of movie sex workers and not mention this insane, entertaining flick? I can guarantee that there are no other cinematic ladies of the night quite like Elizabeth Shelly (Patty Mullen). Frankenhooker might not have won a lot of awards, but for sheer craziness alone, I’m giving its cobbled together streetwalking protagonist a shout-out.  

Dishonorable Mention: Deuce Bigalow- Deuce Bigalow: Male Gigolo and Deuce Bigalow: European Gigolo

Rob Schneider’s sense of humor is almost as off-putting as his personality, which is why I’m glad to give his Deuce Bigalow character a dishonorable mention on this list of movie sex workers. The joke is that his character becomes a gigolo to make some extra cash, but all his clients are “weird and gross.” The problem is that Schneider kind of embodies the idea that “beggars can’t be choosers” (he gets cast as obnoxious, disgusting jerks a lot. I mean, A LOT), and it’s just uncomfortable watching his exploits play out on screen. The thought alone of Deuce Bigalow brands a painful scowl across my face, and while I don’t believe in shaming sex workers, I’m making an exception for this wretched character.

That rounds out my list of the best movie sex workers of all time. That’s just the tip of the iceberg when it comes to cinematic prostitutes, and if you have one you think deserves a spot on the list above, leave a comment below. As always, I’ll be updating this list as new movie sex workers light up the silver screen. So, be sure to check back from time to time in order to see how the rankings might change. Until then, keep it safe and keep it consensual.