It would be hard to find two people more different from each other than Bing Crosby and David Bowie. They were both talented musicians, but that seems to be where the similarities ended. Crosby, the traditional crooner who wore suits and fashionable matching Bailey hats, couldn’t have been more unlike Bowie, whose over-the-top, glam rock persona and gender-bending style revolutionized the worlds of fashion and music. But the holidays are a time for people coming together, and in 1977, this unlikely pair did just that to make Christmas music history.

In September of that year, Crosby was putting together his CBS Christmas special, Bing Crosby’s Merrie Olde Christmas, which would feature special guests from the UK like Ron Moody, Stanley Baxter, and Twiggy. The network was also hoping to appeal to a younger audience, so they asked Bowie to appear as well.

The decision itself was sealed, not by marketing, but by the influence of the two stars’ respective families. Bowie’s mother had long loved Crosby’s music, while Crosby’s teenage children were huge fans of the rock star. Knowing it would make both their families happy, the two ultimately agreed to work together.

Crosby’s daughter recalled to Newsweek, “They sat at the piano and David was a little nervous. Eventually, Dad realized David was this amazing musician, and David realized Dad was an amazing musician. You could see them both collectively relax and then magic was made.”

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