His best-known songs include "Indian Reservation", a 1968 hit for UK singer Don Fardon and a U.S. No.
As a young boy, Loudermilk learned the guitar, and while still in his teens wrote a poem that he set to music, "A Rose and a Baby Ruth".
The owners of local television station WTVD, where he worked as a graphic artist, allowed him to play the song on-air, resulting in country musician George Hamilton IV putting it on record in 1956.
Working out of Nashville, Tennessee, Loudermilk became one of the most productive songwriters of the 1960s and 1970s, penning country and pop music hits for the Everly Brothers, Johnny Tillotson, Chet Atkins, the Nashville Teens, Paul Revere & the Raiders, Johnny Cash, Marianne Faithfull, Stonewall Jackson, Kris Jensen, and Sue Thompson.
Several singers recorded "Midnight Bus"; Loudermilk commented that the best was by Betty McQuade from Melbourne, Australia.
[7] After suffering from prostate cancer and respiratory ailments, Loudermilk died on September 21, 2016, at his home in Christiana, Tennessee.
[11][better source needed] A self-professed prankster,[1] he spun the tale that a Cherokee chieftain, "Bloody Bear Tooth" asked him to make a song about his people's plight and the Trail of Tears, even going so far as to claim that he had later been awarded "the first medal of the Cherokee Nation", not for writing the song, but for his "blood"; further fabricating that his "great-great grandparents, Homer and Matilda Loudermilk" were listed on the Dawes Rolls.