Elisabeth Shue playing a prostitute in Leaving Las Vegas.

In this article, Bernard Weintraub notes that “the first Academy Award for best actress was given in 1928 to Janet Gaynor for her performances in three films, including Street Angel, in which she played a prostitute”.  In fact, there is an interesting pattern of actresses garnering Oscar nominations for playing hookers-with-hearts-of-gold, including Helen Hayes, Julia Roberts, Elisabeth Shue, and Mira Sorivino.  Film scholar Molly Haskell calls Hollywood’s obsession with prostitute figures, “hooker chic.”

http://www.nytimes.com/1996/02/20/movies/play-a-hooker-and-win-an-oscar.html