Bing Crosby was loaned out from Paramount to Columbia for this film and Columbia did no better for him in the way of budget than Paramount. Again relying on Crosby's personality to bring in the box office, if anything Columbia probably spent less money than Paramount on his films.
What they did do was give Crosby a good supporting cast, a role tailor- made for him and a good score of tunes to sing, topped by one of his immortal hits, the title tune Pennies from Heaven. This was the second of 15 movie songs introduced by Bing that were nominated for the Academy Award as best song when that award actually meant something.
Crosby's Larry Poole is a more delineated character than most of the ones he did in the 1930s. He's asked by a prisoner who's on death row to look up the family of a man he murdered and give them the key to an old house that the prisoner owned. He meets up with the family which consists of juvenile Edith Fellows and grandfather Donald Meek. He also tangles with social worker Madge Evans, but in the end all his righted.
In the real world I can't believe that civil servant Evans would ever take up with a vagabond character like Larry Poole, definitely not in this day and age. But if he's played by Bing Crosby, well.........
The film has one other interesting feature. Donald Meek mentions to Crosby a few times that while he's down on his luck now, he expects to come into a regular source of income soon. Finally Bing asks just what is this expected windfall and Meek replies, "The Townsend Plan."
Today's audience would not get that dated bit of humor, but the Townsend Plan was the brainstorm of a Doctor Francis Townsend who was a retired physician who came up with a scheme in which the elderly were to be paid in scrip (in other words money that had to be spent) and then that money would be taxed through the sales which would in turn pay for another month's scrip and so on and so on. At the time of the filming of Pennies from Heaven this plan had a lot of followers in the country which was in a depression.
Of course Townsend never got his plan passed, but a lot of historians credit him with raising such a fuss over what we did with our elderly that the result was Social Security.
One of Bing's best.