 Ramba uchiverenga ndima ino - Jennings akatanga kuridza gitare aine makore masere uye akatanga kuridza pazera remakore 12 panhepfenyuro yeKVOW, pashure pacho akaumba boka rake rokutanga, The Texas Longhorns. Jennings akasiya chikoro chesekondari pazera remakore gumi nematanhatu, akatsunga kuva muimbi uye akashanda semutambi uye DJ paKVOW, KDAV, KYTI, KLLL, muCoolidge, Arizona, uye Phoenix. Muna 1958, Buddy Holly akaronga kurekodha kwekutanga kwaJennings, ndokumukweretesa kuti aridze bass. Jennings akasiya chigaro chake mundege ine ngwavairamuna 1959 yakadonha ndokuuraya Holly, J. P. The Big Bopper Richardson naRitchie Valens. 