A Trailer for Every Academy Award Winning Movie Ever/WMG

Who would really be playing the film's characters?
Post your theories. This troper's:
 * Wealthy, Successful Protagonist - George Clooney
 * Free-Spirited Girl - Kate Winslet(almost too obvious)
 * Disabled Guy(desperately trying for an Academy Award) - Edward Norton
 * Older actress trying for a comeback - Holly Hunter
 * I say if they don't get Kate Winslet, they probably would get Natalie Portman. I don't think they would get George Clooney (he's a little old), probably either Eric Bana or Christian Bale.
 * How about George Clooney in drag for Older Actress Trying For A Comeback?