Bob Montgomery was the songwriting partner and best friend of Buddy Holly. He met Holley (as his name was then spelt) at Hutchison Jr. High in 1949. Billed as "Buddy & Bob", they played junior high assemblies. Classmates included Jerry Allison, who later became one of the original Crickets.

Local radio advanced their reputation. KDAV, the nation's first all-country radio station, held a weekly show where Buddy and Bob's popularity grew so much they were given their own half-hour program each Sunday. Their repertoire remained basically country with Bob Montgomery singing lead. At every opportunity, the boys would cut demonstration records. Generally, they invited local musicians, including Larry Welborn on bass and Sonny Curtis on guitar, to join them. They sent their demos to record companies, hoping they'd be offered a recording contract.

In addition to airing the 'Sunday Party', KDAV also sponsored live country and early rock 'n' roll concerts in Lubbock. The station often chose the "western and bop" duo to open the shows, which headlined stars like Ferlin Husky, Marty Robbins, Porter Wagoner, even Elvis. One of these performances played a crucial role in the advancement of Buddy's career. On October 14, 1955, Bill Haley and the Comets starred in a show at the Fair Park Auditorium. Eddie Crandall, Marty Robbins' manager, spoke to Pappy Dave Stone, the owner of KDAV, and asked for some of Holley's demos after hearing his performance earlier on the same bill. The records ended up in the hands of Paul Cohen, head of Decca Records' Specialty Division. And from those hands came the contract offer, made out to "Buddy Holly".

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