4. MIRA SORVINO AS LINDA ASH IN MIGHTY APHRODITE (1995)

In Mighty Aphrodite, Woody plays a sportswriter who seeks out his brilliant adopted son’s biological parents. As luck would have it, the boy’s birth mother is a sexy, seemingly ditzy, prostitute and porn actress played by Mira Sorvino, daughter of Goodfellas actor Paul Sorvino. Without revealing their connection, he tries to help her turn her life around, and eventually sleeps with her.

Now, we doubt that many women dream of bedding Woody Allen in real life or on screen, but as it turns out, signing on for the project was one of the best decisions that the beautiful blonde actress ever made, as she took home the Best Supporting Actress Oscar for it. Worth it? Definitely. Still icky? Obviously.