100 Greatest Men: The Complete List Waylon Jennings was the very embodiment of the country music outlaw movement in the seventies, demonstrating that legendary music can be made if artists are liberated to create it in the way that they want to. Jennings was born in Littlefield, Texas, and was playing the guitar and singing on the radio by the time he was twelve years old. Jennings dropped out of school at age fourteen, and picked cotton while pursuing music in his spare time. When he moved to Lubbock, he became friendly with rising rock star Buddy Holly, who took Jennings under his wing. Holly produced a single for Jennings and had him fill in as a bass player in the Crickets.