He won twice, for The Awful Truth in 1938 and Going My Way in 1945.
Have you seen the video of Frank Capra presenting it to him and then trying to wrestle it away from him? It’s a priceless bit. Such good-natured, competitive comeraderie. Hope it still exists today.
Questjonmark
I have come to believe, (closer everyday to being convinced) that since Mr. McCarey was not nominated in 1937 for “Make Way for Tomorrow,” but for “The Awful Truth” instead; and since only picture directors vote for the director’s category; his fellows, (collaboratively, or not) voted to give him the Academy Award for this film (out of professional reverence) rather than for the one which he was actually nominated.