Songfacts®:

• This song was one of the biggest hits of the 1930s, and reflects the history of that period. It starts with a reminiscence of when the best things were free (the Roaring Twenties), and ends with encouragement to not give up but to wait out the storm (the Great Depression) because good things will follow.
  
  Pennies from heaven are sign of serendipity. In this song, no matter how much it rains, it will all turn out OK in the end. This optimistic sentiment was especially relevant to a Depression-era audience.
• "Pennies from Heaven" was written by Johnny Burke and Arthur Johnston for a 1936 movie by the same name. This was the first of many hit lyrics that Johnny Burke wrote for Bing Crosby. The song, originally performed by Bing Crosby with Jimmy Dorsey and his orchestra, received the movie's only Academy Award nomination, but lost to "The Way You Look Tonight."
• Billie Holiday also released a version of this song in 1936. Since then, it has also been recorded by Frank Sinatra (two versions – one with Count Basie), Louis Armstrong, Tony Bennett, Dinah Washington, Arthur Tracy, Big Joe Turner, Stan Getz, Dean Martin, Louis Prima, Andy Williams, The Skyliners, Michael Bublé, and many other singers.
• Louis Prima recorded an abbreviated version of this song for his 1957 The Call of the Wildest album. His jubilant rendition was used in the 2003 movie Elf (when Buddy the Elf finds many fun new things in New York City, including revolving doors, discarded bubble gum on subway railings, and the world's best cup of coffee) and the 2008 movie Igor.