Ukelele Ike, Singin’ in the Rain, 1929
Ukelele Ike, aka Cliff Edwards, best known as the voice of Jiminy Cricket, also had a hit in 1929 with Singin’ in the Rain, later used in the 1952 film of the same title.
Here he is performing the song in the film The Hollywood Revue of 1929, one of the earliest talkies, with the Brox Sisters, the Rounders, and the M&M Chorus.
I first saw this clip in a set of dvd extras on the history of the movie musical. There’s a mix of dreamlike and goofy about it that I find delightful.