The Great Gatsby,
I thought it would be time to post a picture of F Scott Fitzgerald (the subject of the movie) in college drag.
Buzzfeed reported that the photo was snapped in 1916 when the future "Great Gatsby" scribe was in his third year at Princeton University. Fitzgerald was then performing a play called "The Evil Eye," which he also wrote the lyrics for, with a musical-comedy troupe known as the Princeton Triangle Club.
I have no idea if this movie version of Fitzgerald's life covers his college years or female impersonation days but star Leonard DiCaprio just still may be pretty enough to pull it off!