Bing Crosby recorded the biggest-selling single of all time, ‘White Christmas’, on 29th May, 1942. The session took just 18 minutes, and the song was not considered the standout from the album: everyone thought the Valentine’s-themed ballad ‘Be Careful, It's My Heart’ had a better chance of chart success.

The songwriter, Irving Berlin, was perhaps not an obvious person to pen the quintessential American Christmas song, given that he was a Russian-born Jew, who had never celebrated the holiday until his arrival in the United States. But the record’s airplay on US Army overseas radio stations during World War II struck a chord with homesick soldiers, and helped embed the tune deeply into the American psyche.

In this episode, Arion, Rebecca and Olly reveal why the version you’re almost certainly thinking of is NOT the version with which Bing initally topped the charts; unpick the confusing Russian Doll stack of genres into which the song has been repurposed; and explain why Berlin’s Oscar win became a pivotal moment in the Academy Awards ceremony… 

Further Reading:

• ‘'White Christmas' at 75: A Snapshot of the Most Successful Song In Music History’ (Billboard, 2017): https://www.billboard.com/culture/lifestyle/white-christmas-bing-crosby-history-8071111/#!

• ‘Is White Christmas the Best Popular Song Ever Written?’ (Smithsonian Magazine, 2012): https://www.smithsonianmag.com/smithsonian-institution/is-white-christmas-the-best-popular-song-ever-written-165989545/

• ‘Holiday Inn | Bing Crosby Sings "White Christmas"’ (Universal Pictures, 1942): https://www.youtube.com/watch?v=GJ36gbGlm8Y

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The Retrospectors are Olly Mann, Rebecca Messina & Arion McNicoll, with Matt Hill.
Theme Music: Pass The Peas. Announcer: Bob Ravelli. Graphic Design: Terry Saunders. Edit Producer: Ollie Peart.
Copyright: Rethink Audio / Olly Mann 2026.

This episode originally aired in 2024.

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