He hovered around the deep background of the New York music scene in the late '50s and early '60s, following the age-old career advice whose source is long forgotten: "Bang your head against the wall until you see a crack, then continue banging your head against the wall." The small cracks that appeared for Roy Benson include his absorbing song "Korea's Mountain Northland", covered by country singer Marvin Rainwater, and the signing of what was known as a "standard" six month contract with Beacon records as a member of a vocal group known as the Pageants. Rainwater is sometimes accused of exploiting his native American ancestry for country and western glory, nonetheless he is a solid performer and the Benson song can be considered either ahead of its time or the victim of a lack of exposure. Either way, the hit parade audience wasn't quite ready to grab onto such a stark depiction of wartime pathos, especially from an artist who was best known for the upbeat musical promise "Gonna Find Me a Bluebird". Yet later songs in exactly the same vein made a big impact on the charts, whether it was Barry Sadler and the "Ballad of the Green Berets" or any of the September 11, 2001 exploitation songs.
The Pageants represented Benson's most successful performing venture, and had the benefit of recording with a superb back-up band that included ace guitarist Larry Lucie, the well organized Sticks Evans on drums and bassist Bob Bushnell, the fellow who provided the bottom end throttle on quite a few classic Elmore James recordings. Benson's fellow bandmembers were Barbara Reeves, John Flores and Melvin Riley. The Pageants' recording pageant consisted of four songs, two of which were released on a Beacon single in 1963.