For me I think it was Jack Black in King Kong. I just wasn’t prepared for Jack Black being in a more serious role.
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Kind of a cliche answer now, but at the time, everyone was shocked by Heath Ledger’s casting as Joker.
Similarly, I was initially skeptical when Robert Pattinson was announced for The Batman. But I thought he did a fantastic job!
Seems to be a tradition. Back when Michael Keaton was announced as Batman nobody could see him in that role either. He was only doing comedies at that time.
Robin Williams in One Hour Photo. He did such an amazing job but it was just so unexpected at first to get over that he was doing a serious role that was a psychopath.