Actor: Bing Crosby

Bing Crosby won Best Actor for Going My Way and was among the most commercially successful entertainers of the twentieth century in any medium.

White Christmas, which he introduced in Holiday Inn, remains the best-selling single ever released. The Country Girl gave him a serious dramatic role as an alcoholic, and he was an early investor in videotape technology, which is a genuinely consequential business decision nobody credits him for.