Perhaps a little known fact is that Buddy Holly gave a teenaged Waylon Jennings his start in music, and was his mentor. This was after a contract dispute with the record company that forced Holly to go on tour without his backing band. Tour was taking place during horrible conditions in a busted up tour van during the dead of winter. Buddy Holly chartered a plane for his 3-piece band to fly to their next show just to but time to rest and do laundry.
A 19yo Jennings gave his seat up to the Big Bopper, who had the flu at the time. The other bandmate gave his seat up to Richie Valens. In keeping with how much **** they talked to each other, Holly left for the plane and told Jennings that he hoped the bus would break down. Jennings told the 22yo Holly that he hoped his plane would crash, which it did, killing all on board. This became the inspiration for the Don McLean song, "American Pie". Jennings blamed himself for the accident for a long time and quit music altogether for a couple of years and moved to Arizona, before his brother encouraged him to get back into it. Which he did, eventually becoming the leader of the "outlaw" country music genre in the 1970s, along with Willie Nelson and a few others.
These pics of and with Buddy Holly were taken in 1959 in a Grand Central Station photo booth.