Tootsie

I don't care if this movie is about as old as I am, it's awesome. It is the hilarious story of a NYC actor who, desperate to get work so he can fund his friend's play, dresses up as a woman in order to get a part in a soap opera. Things only get more complicated from there. Wonderful writing, acting, casting, directing, you name it; still as great today as when it first appeared. Look for it here.