Bing Crosby filmography – Wikipedia

Bing Crosby and Fred Astaire: A Couple of Song and Dance Men (1975) Songs nominated for Academy Award. From 1934, when the first Oscar was awarded for “Best Song”, until 1960, Bing Crosby introduced more nominated songs than any other singer. His fourteen nominations produced four Oscar winners, a record that has never been matched.

https://en.wikipedia.org/wiki/Bing_Crosby_filmography