Pennies from Heaven
Starring Bing Crosby with Louis Armstrong (first top billing for a Black Perfomer in Film)
Directed by Norman McLeod
(also known for two Marx Brothers films)
1936
No White Christmas in this flick, but perhaps an even more timely weather metaphor. Bing Crosby plays a jailed busker from Mukilteo, Washington (Crosby was actually born in Tacoma and raised in Spokane). A death row inmate makes a final request of Crosby to assist the family of his victims, a young female 'orphan' and her grandfather.
Like many successful depression era movies it is upbeat, and a window into the time. It is no wonder that Crosby would go on to inspire many, including just about every American GI in WW2 and Frank Sinatra.
Below is the title song. The film's piece by Louis Armstrong is every bit as good and not to be missed.