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The best recent example I can think of in that category was 2012: Waltz (won his 2nd in the category), TLJ (previous winner), De Niro (previous Actor/SA winner), PSH (previous Actor winner), Alan Arkin (previous winner).Best supporting actor sure has some blockbuster names..
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This year: Pitt (hasn't won an acting Oscar), Hopkins (previous Actor winner), Hanks (previous 2 x Actor winner), Pesci (previous winner), Pacino (previous Actor winner)
And even though Pitt is the only non-winner of the 10 (shortly to be rectified), he has won an Oscar for producing a Best Picture.