>Here’s a little interesting side-by-side (or top-over-bottom)…

An excerpt from Pennebaker’s documentary on Bob Dylan, Dont Look Back (1967):

Cate Blanchette as Dylan in the upcoming Tod Haynes film, I’m Not There (2007):

Personally, I think it kinda works for Cate to play Bob, especially from his “androgynous” years. But it still looks like a woman portraying a man. In that sense, it may “work” even better.