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He met Buddy Holly at school, and they were both learning instruments.

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There were a lot of duet harmony records we liked, bluegrass stuff.

We started playing those songs in school talent shows and we eventually had our own little radio show on KDAV."When they had earned a little money they recorded demonstration records in Wichita Falls and at Norman Petty's studio in Clovis, New Mexico.

He wrote two hits for British artists: "Somebody Else's Girl" (Billy Fury, 1963) and "Wind Me Up (Let Me Go)" (Cliff Richard, 1965).

Montgomery produced and published "Honey" for Bobby Goldsboro, which was written by Bobby Russell.

His son, Kevin became a singer and songwriter who recorded a duet of "Wishing" with Mary Chapin Carpenter, produced by his father, for a Buddy Holly tribute album.