As a young boy he learned to play 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 the local television station, 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. After Eddie Cochran had his first hit record with Loudermilk's song "Sittin' in the Balcony", Loudermilk's career path was firmly set.