Buddy Holly and Waylon Jennings, two Texans, grew incredibly close friends having met randomly while both were dining in a restaurant as teenagers.

Their friendship, built on their love for music, would see Holly take Jennings under his wing while his popularity began to rise considerably as became a central and pioneering figure of mid-1950s rock and roll.

Holly would contribute some guitar samples to Jennings’ first recording session in 1958 and, in return, Jennings joined Holly’s band as part of his three-week tour titled the ‘Winter Dance Party’—a tour which would infamously end in severe disaster.

Prior to embarking on their tour together, Holly and Jennings were hanging out in New York City and played around in a photobooth located in Grand Central Station, posing for a pictures as the two smoked cigarettes and joked around.

Skip to February 3rd, 1959, one of the single largest damaging moments in musical history befell some of rock and roll’s most promising stars and will forever be known as ‘The Day The Music Died’. Ahead of their tour, Holly’s band had repeated issues with the tour bus freezing over and breaking down. Opting to find an easier way to make their scheduled tour, musicians Holly, Ritchie Valens, and ‘The Big Bopper’ J. P. Richardson decided to fly to Moorhead, Minnesota.

However, their flight would never reach the destination and instead fatally crashed and killed all those on board.

Jennings, with the photobooth pictures in his pocket, was due to be on the flight but instead opted to swap with Richardson as ‘The Big Bopper’ was suffering from flu. Holly, joking with his good friend, told Jennings: “Well, I hope your ol’ bus freezes up!” as he prepared to head to the airport.

Jennings, laughing and readying himself for a long road trio, replied: “Well, I hope your ol’ plane crashes!”

With words that haunted him for the rest of his life, Jennings was left with music, memories and photographs of his ol’ buddy. Below, enjoy one of the last known pictures of two friends taken:

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