First performed and recorded by Ukulele Ike (1929).
Also performed by Judy Garland (1940).
Most familiar version performed by Gene Kelly (1952).
From the wiki: “‘Singin’ In the Rain’ is a song with lyrics by Arthur Freed and music by Nacio Herb Brown, published in 1929. However, it is unclear exactly when the song was written; it has been claimed that the song was performed as early as 1927.
“We do know it was first performed by Doris Eaton Travis in the 1929 revue The Hollywood Music Box Revue. The song became a hit and was recorded on disc by a number of artists, first and most notably Ukulele Ike (Cliff Edwards) who would also perform the number on-screen with the Brox Sisters in the early MGM musical The Hollywood Revue of 1929. The song was recorded by Annette Hanshaw in her album Volume 6, and on film by Jimmy Durante in Speak Easily (1932), and by Judy Garland in Little Nellie Kelly (1940).”
Ukulele Ike & The Brox Sisters, “Singin’ in the Rain” from The Hollywood Music Box Revue (1929):
Judy Garland, “Singin’ in the Rain” (1940):
Gene Kelly, “Singing’ in the Rain” from Singin’ in the Rain (1952):