 He was the first to record the Mel Tillis song "Ruby, Don't Take Your Love to Town", which became a top ten hit for him in 1967 and later a hit for Kenny Rogers.This was followed by his performance of Dallas Frazier's "the Son of Hickory Holler's Tramp" in 1968, and the crossover hit "With Pen in Hand", which would later become a hit for Vikki Carr.In the 1970s, Darrell was associated with the Outlaw country movement.