From Colin Miller:
What individual was nominated a total of two times in a category and won two Oscars in that category but did not win an Oscar each time that she or he was nominated?
Oscar Countdown: Day 16
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Peter O'Toole?
Peter O'Toole has been nominated for 8 Oscars for Best Actor and has not (yet) won although he was awarded an honorary Oscar.
Here's a hint: The category was Best Cinematography.
Looks like it might've been Hal Mohr, who is the only successful write-in winner for an Academy Award ever. I wonder what the list of winners would look like today if the Academy hadn't changed the rules to prohibit write-in votes.
Yes, Hal Mohr is the correct answer. He was nominated for (1) "Phantom of the Opera" and won and (2) "The Four Poster" and lost. He was not nominated for "A Midsummer Night's Dream" because of his arbitration efforts during the Hollywood strike of 1933. Nonetheless, he won the award after a vigorous grassroots write-in campaign. The next year, the Academy decided that it would not longer accept write-in votes.