7. Dustin Hoffman - Tootsie
In Tootsie, Dustin Hoffman plays a failing New York actor who, having tried everything else, decides to pose as a woman to get more roles. Because obviously there's plenty of roles for middle-aged non-beauty queens. Surprisingly, a soap opera casting director likes her pluck, and Tootsie becomes one of the most popular new actors on the scene. I see no possible way this could go wrong. Dustin Hoffman has recently opened up about this role, discussing his journey from man to relatively unattractive woman. When they finalized the makeup design, he recalled asking to be made prettier, only to be told "that's about as good as it gets". Playing this somewhat frumpy-looking character made him reconsider how he viewed women in the future, and created an all-time comedy classic along the way. Not too shabby!