Ah ha!!
1933 Hallelujah, I'm A Bum
Starring Al Jolson with Madge Evans, Frank Morgan, Harry Langdon and Chester Conklin.
Quite a different movie, Jolie plays Bumper, a hobo whose close friend just happens to be the mayor of New York. The interesting sidenote to this picture is the title, itself, which was changed to Hallelujah, I'm A Tramp for release in England, where "bum" has a more vulgar meaning.