Pennies from Heaven
In prison, Larry Poole (Bing Crosby), a self-described troubadour, is approached by an inmate named Hart (John Gallaudet) who is on his way to the electric chair. Hart asks Larry to deliver a letter to a family called Smith near Middletown, New Jersey. After finding the family, which consists of a grandfather (Donald Meek) and a young girl named Patsy (Edith Fellows), Poole tells them that the letter holds a key, reveals that the condemned man had unintentionally killed Patsy's father and that he is giving the Smith family his old house and former hideout, the only thing he has to give as atonement.
Susan Sprague (Madge Evans) represents the county welfare department and it is her job to see that Patsy is raised "properly", or the girl will go to an orphanage. A variety of misadventures befall Larry as he tries to help "Gramps" out with Patsy to save her from the orphanage, all while Susan and he are falling in love, paternally.
To get cash for a restaurant license, Larry gets a stunt job at the circus, but is injured. While he is in hospital Gramps comes to let him know that the county has taken Patsy away. Larry believes Susan went behind his back and had Patsy placed in the orphanage. It is discovered that Susan had no part in it, but she loses her job defending Larry and his care of the child.
Larry has the circus perform for the children so that he can 'break Patsy out', when Patsy lets Larry know how Susan feels about him. Their attempt to free Patsy fails. Afterwards, Larry finds out that Susan has gone to New York and he goes there to find her.
While in New York, Susan is approached by two policemen looking for Larry, not to arrest him as she suspects, but to bring him back to the head of the County Welfare Department to help deal with Patsy, who has gone on a hunger strike. The policemen are watching Susan's apartment in the hopes that Larry will show up. When he does, they make him leave with them, after he and Susan reveal their feelings for each other.
When they return to the orphanage, the head of the welfare department begs Larry to help them with Patsy. Larry agrees to adopt Patsy and raise her with the help of Susan, who agrees to marry him and be a mother to Patsy.
depressing