Bill Emerson had been a member of the Country Gentlemen, one of the defining Washington DC-area bluegrass acts of the late 1950s and 1960s, bringing a technically accomplished and stylistically flexible banjo style to a band known for its adventurous repertoire choices. Cliff Waldron was a guitarist and vocalist active on the same Washington-area circuit, part of the dense network of bluegrass pickers who performed at parks, clubs, and radio stations throughout the DC, Maryland, and Virginia region during the genre's postwar growth years.

Their 1968 Rebel Records release — "Deep River" / "Over Yonder Stands Little Maggie" (Rebel F 281) — documents the Lee Highway Boys configuration, a group named for the route running through Northern Virginia that had become something of a symbolic address for the area's bluegrass community. The single places them squarely within the Rebel Records roster of the era, a label that had made the DC-area scene its particular province and was in the process of building what would become an authoritative catalog of traditional and progressive bluegrass from the region.

The pairing of "Deep River," a gospel-inflected number, with "Little Maggie," one of the oldest and most widely recorded pieces in the bluegrass and old-time repertoire, reflects a programmatic approach common to bluegrass singles of the period — balancing sacred and secular material, traditional and contemporary within the same release. Emerson and Waldron would continue as a working partnership into the early 1970s, recording additional material for Rebel and contributing to the sustained vitality of Washington-area bluegrass during a period when the scene was developing its own distinct identity within the genre.

Session details drawn in part from the Bluegrass Discography.