This one's actually a little tricky. No one had won three Oscars
for a single film when Leo McCarey won Best Director and Best Original Story
for Going My Way in 1944, a film he also produced. Going My Way was also
named Best Picture, and since that award usually goes to the producer,
McCarey would seem to be the answer.

Not quite. In the days of the studio system, studio heads sometimes
accepted the Best Picture Oscar instead of the producer. This was the
case with Going My Way, when Paramount head of production Buddy DeSylva
accepted the award instead of McCarey (Bob Hope was on suspension
by Paramount at the time, and when DeSylva went to the stage to receive the
Oscar, Hope got on his knees and feigned shining the executive's shoes).

Billy Wilder was the first to actually take home three Oscars for a single film,
for writing, directing and producing the Best Picture of 1960, The Apartment;
and he is cited by most sources as the answer to the question. But since we
made you read this lengthy answer, full credit if you said McCarey instead.

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