In 1949 12-year old Waylon Jennings marched himself into the studios of 1490 KVOW-AM in Littlefield, TX to audition. GM J.B. McShan liked the kids routine and gave little Waylon a 30-minute weekly program. This was Waylons first band, The Texas longhorns which included Emil Macha on washtub bass and Roscoe Taylor on banjo and according to one source 'a 390 lb mandolin player named 'tiny'. True or not, it's sufficiently mythical to be included here for entertainment value.They recorded a demo at KFYO, and Jennings DJ'd briefly on the "Sunday Party" program on KDAV. When he turned 18 he relocated to Lubbock and got a steady gig behind the mic at KLLL a direct competitor for KDAV. It was there at KLLL that he met Buddy Holly. Buddy recorded a demo at KLLL and if Waylon asn't manning the reels I'll bet he was in the room.
Holly produced two songs for Waylon at Petty Studios in Clovis, NM. Holly played guitar on both, and the record was released on Brunswick in 1959. They became friends and Waylon was hired to be the bassist on Buddy Holly's Winter Dance Party Tour in 1959. That was the fateful tour in which Buddy Holly's plane crash killing him, Ritchie Valens, and the Big Bopper. The tour continued without Buddy with Waylon singing lead. More here.
After that fateful tour Waylon returned to DJing at KLLL. He and his family moved stopped over in Coolidge, AZ where they stayed with his wife Maxine's sister. He got another radio gig this time working for Earl Perrin of Gila Broadcasting on his fledgling radio network. Waylon worked out of KYCY right in Coolidge. KYCY had a strange dual heritage as both a Mutual radio network member and a Network of Arizona Station. Earl Perrin owned the latter. Earl Hickman owned the former.
Perrin ended up owing Gila something like 30,000 dollars and went nearly bankrupt. Waylon exited stage left and went to Phoenix. The stage was calling Waylon he became an outlaw country musician and never went back to radio. His album "the Outlaws" was the first country album to be certified platinum. He died in 2002.