 After a stint in the army, he moved to Nashville and began managing a Holiday Inn near Music Row when he was discovered by Kelso Herstin, a producer working for United Artists, on the recommendation of Bobby Bare.In his recording career, Darrell established a trend of introducing "lyrically adventurous" songs that later became major hits for other artists.His first single, a version of Curly Putman's "Green Green Grass of Home" was issued in 1965, followed by "As Long as the Wind Blows" in 1966 which made the country Top 30 and saw Darrell being named "Most Promising Male Artist" by Cashbox.