prolly not his best but certainly most underrated is burn after reading he is hilarious in it. a great comic actor in general.
i think he's the low point of tree of life (not that that's saying much) as i don't think he conveyed the vulnerable side of the father character which made the whole family dynamic more 2D than it was designed to be.
zero use in dwelling on what could have been but ledger was perfect casting and if he'd lived to do the role i think the film would have gone supernova