64 Rare Historical Photos

Waylon Jennings, Buddy Holly and someone's middle finger goofing around in a NYC photo booth, 1959.
Source: Pinterest
Holy cow - look at these two hipsters. This photo looks like it was taken last week. But this is actually Waylon Jennings and Buddy Holly circa 1959 - having a laugh in a NYC photo booth. Not only were these two music icons friends, but Jennings was slated to be on the doomed plane that crashed and killed Holly, The Big Bopper, and Ritchie Valens in 1959. Don McLean deemed it the day the music died in his song, American Pie.

Jennings was hired by Holly to play bass for him on the Winter Dance Party Tour - which was on route from Clear Lake, Iowa to Minnesota. Jennings gave up his seat on the plane to The Big Bopper - and took the tour bus instead.

Before taking off, Holly jokingly told Jennings that he hoped the bus broke down. In jesting manner Jennings replied, “I hope your ol’ plane crashes.”

And the rest is history.
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