1. McCabe & Mrs. Miller
2. Moulin Rouge
3. Midnight Cowboy
4. In the Realm of the Senses
5. Last Exit to Brooklyn
6. Hustle & Flow
7. Leaving Las Vegas
8. Taxi Driver
9. Mysterious Skin
10. Unforgiven
L.A. Confidential has a potential Top 5 movie prostitute, but is not a top film about prostitution
While True Romance is a great film, its view of prostitution is such male wish fulfillment fantasy that I disqualified it from this list. Same for Sin City.