I think the moustache worked. And that was the hip thing for questionably gay guys, having a moustache in the late seventies/early 80's. Besides, could you expect them to have the same look for 20 years, plus look at the evolution of the sideburns.

Anne Hathaway arguably has the prettiest eyes in movies, but yes that wig was hideous. For a much more "natural" looking Hathaway, I'd recommend Havoc, certainly a much more sexually charged role. As for the instigator of the relationship here, I'm not surprised either. From the outset Jack was the wild talkative one, so not surprising on that end. Hearing so much about Heath Ledger's performance, I'm actually a little sorry for Jake Gyllenhaal who's probably never been better, and may never be better.