Men played women's roles in Shakespeare's time because the theater was already controversial as it was much less with women actively participating in it by being members of troupes. Actors were looked down upon. I don't see how this convention was particularly brutal. It was the 16th century, the social codes of the day which were sexist. Women didn't perform Shakespeare until 1660. White people performed as black characters in plays but this did not involve emulation or caricature of supposed innate qualities of blackness like blackface minstrelsy did. Professor Shurtz was undertaking emulation but not necessarily caricature. Blackface as entertainment lasted in the US until the mid-1960's before civil rights groups raised awareness and people stopped doing it. 
Men dress in drag all the time so clearly it's not taboo. Also, I can't figure out the connection you are attempting to make between men cross-dressing and atrocities against women. You seem to be straining yourself a bit