By our count, Bing Crosby sang 14 nominated songs in their original films --
4 Best Song winners:
"Sweet Leilani" from Waikiki Wedding (1937)
"White Christmas" from Holiday Inn (1942)
"Swinging on a Star" from Going My Way (1944)
and "In the Cool, Cool, Cool of the Evening" from Here Comes the Groom (1951) (w. Jane Wyman)
Crosby also performed the following 10 Best Song nominees:
"Love in Bloom" from She Loves Me Not (1934)
"Pennies from Heaven" from Pennies From Heaven (1936, uncredited)
"Only Forever" from Rhythm on the River (1940)
"Ac-Cen-Tchu-Ate the Positive" from Here Come the Waves (1945)
"Aren't You Glad You're You" from The Bells of St. Mary's (1945)
"You Keep Coming Back Like a Song" from Blue Skies (1946)
"Zing a Little Zong" from Just for You (1952) (w. Jane Wyman)
"Count Your Blessings Instead of Sheep" from White Christmas (1954)
"True Love" from High Society (1956, uncredited)
"The Second Time Around" from High Time (1960, uncredited).