Most Oscar award winning songs sung by the same person

According to Official Guinness Records,

During his career, Bing Crosby (USA, 1903– 1977) sung four Oscar winning songs from the films he had starred in between 1937 and 1951. The first was 'Sweet Leilani' from Waikiki Wedding (USA 1936), which won in 1937, followed by 'White Christmas' from Holiday Inn (USA 1941) in 1942, 'Swinging on a Star' from Going My Way (USA 1943) in 1944 and 'In the Cool, Cool, Cool of the Evening' from Here Comes the Groom (USA 1950) in 1951.
In second place is Bob Hope, Frank Sinatra and Jennifer Warnes (all USA), having sung three winning songs.

For a complete list of 1951 records, please visit 1951 Guinness Records in United States.

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