Bailey got his first experience of musical performance as a member of his high school's Future Farmers of America string band.

After graduation, he married and had children immediately and had little time to pursue his career,[3] but he spent many years playing occasional gigs at honkytonks in Georgia and Alabama and developing his songwriting.

[2] The song failed to hit the charts at that time, but Bailey was encouraged, forming the pop trio Daily Bread which released a pair of albums on small labels.

[3] As his songwriting talents became known, Bailey signed with RCA Records and, in 1978, began releasing singles of his own songs.

[2] Bailey had three double sided number 1's in succession on the Country chart,[2] a feat never accomplished by any other artist.