You Are My Sunshine / Singing in the Rain by Caravan of Thieves

First recording and first release by The Pine Ridge Boys (August 22, 1939 / October 6, 1939)

First recording by The Rounders [US1] (April 26, 1929)

First theatrical release by Cliff Edwards, Brox Sisters, Rounders and MGM Chorus (July 20, 1929)