I like the version of Man of Constant Sorrow on Oh brother...
Granted, i haven't heard any other versions...:0)

Just a thought on changing genders- it's a lot more fun not to. I once sung the Kinks' All Day and All Of THe NIght, including 'girl i want to be with you all of the time' and accompianied by a lot of, um, suggestive posturing...that got a good reaction. I did get hit upon by a couple of ladies afterwards, though! :0)

I recently heard the Whites Stripes song Fell in Love with a Girl sung as fell in love with a boy, and i just thought, 'well, it's ok-but what's the point?'