Pennies from Heaven(1936)

FUN...when Crosby croons himself out of jail and lands on a merry-go-round with the meanest of brats!

Larry Poole, in prison on a false charge, promises an inmate that when he gets out he will look up and help out a family. The family turns out to be a young girl, Patsy Smith, and her elderly grandfather who need lots of help. This delays Larry from following his dream and going to Venice and becoming a gondolier. Instead, he becomes a street singer and, while singing in the street, meets a pretty welfare worker, Susan Sprague. She takes a dim view of Patsy's welfare under the guardianship of Larry and her grandfather and starts proceedings to have Patsy placed in an orphanage.