Composer Jimmy Webb was first to record "The Highwayman" for his 1977 album "El Mirage" produced, arranged, and conducted by George Martin, . Among his bona fide hits: Up, Up and Away", "Didn't We", "By the Time I Get to Phoenix", "Wichita Lineman", "Galveston", "The Worst That Could Happen", "All I Know", and "MacArthur Park". According to wikipedia Jimmy Webb is the only artist ever to have received Grammy Awards for music, lyrics, and orchestration. Why he was never successful as a performer/recording artist is beyond me.

"Super group" The Highwaymen (Willy Nelson, Waylon Jennings, Kris Kristofferson and Johnny Cash) recorded the hit version in 1985 breaking into the top one hundred and it peaked at the top of the country chart.