When the Grammys hit the air this Sunday night, I don’t expect to see anybody up on TV announcing the winner in the Best Historical Album category–I’m sure it’ll be one of the many awards dispensed with inconspicuously, like Best Spoken Word Album for Children. But it’s one of the most interesting categories this year.

Reissues of Lester Young’s work with Count Basie and Nina Simone go up against three sublimely obscure collections, including one that isn’t even music–Debate ’08: Taft and Bryan Campaign on the Edison Phonograph (released by Archeophone, a Champaign-Urbana label I profiled in 2007) compiles 22 Edison wax cylinders cut in 1908 by the presidential campaigns of William Jennings Bryan and William Howard Taft.

The third nominee is Art of Field Recording Volume I: Fifty Years of Traditional American Music Documented by Art Rosenbaum, a typically terrific release on the Dust-to-Digital imprint that compiles recordings overseen by the record collector named in its title. (The label has just released the equally impressive second volume.) But the fourth, Polk Miller & His Old South Quartette (Tompkins Square), is probably the weirdest. Inside its beautiful package–Susan Archie, who worked on Revenant’s amazing Charlie Patton box, handled the art direction–is a fascinating and disturbing relic of the minstrelsy era. Miller, a white southerner from a slave-owning family, toured and recorded in the early 20th century with a black vocal quartet, singing the songs of the plantation.

Bearing in mind who’s performing this music, it’s hard to imagine something more fucked-up than the opening track, a former Confederate battle anthem called “The Bonnie Blue Flag.” (Like the six tracks that follow it, it was recorded in November 1909.) As David Wondrich wrote in his 2003 book Stomp and Swerve, “One wonders what the poor bastards in the OSQ thought about this one. It couldn’t have helped that their record company singled Miller out for his efforts ‘to bring the ruling race an appreciation of the characteristics of the Negroes.'”

Miller was born in Virginia in 1844, grew up on his father’s plantation, played guitar and banjo, fought for the Confederacy, and owned a pharmacy. He formed this act sometime between August 1899 and April 1903. The OSQ toured the country, particularly the eastern seaboard, and became quite popular. Mark Twain called their song “The Watermelon Party” (which is just as tasteless as the title implies) a “musical earthquake,” which won’t surprise you if you’ve read Innocents Abroad and know what a bigoted jerk he could be.

Miller clearly wasn’t any sort of civil rights advocate either. In a story in the Richmond Journal on January 3, 1912, where he announced his decision to break up the group, he insisted that his presentations were intended to be educational–for the benefit of those “who never enjoyed as I did the kind ministrations of the old Negro mammies and Uncle Toms of ante-bellum days.” Then he made sure everyone knew he didn’t see the singers in the quartet as his equals: “They were subservient to my will.”

The last seven cuts on the disc were recorded in 1928 by a later version of the Old South Quartette, which continued to perform on its own after Miller threw in the towel. But those tracks aren’t all that different, displaying many of the same unfortunate “coon song” characteristics. Throughout the collection the group does a fine job, especially considering how hackneyed the songs are, but compared to blues and jazz–African-American forms that were evolving swiftly during the decades bookended by this release–the material is pretty hard to swallow, a white racist idealization of the music of the “southern Darkey.”

This music has been available previously through the Austrian label Document, but without this reissue’s liner notes, photographs, and other images–background material that makes it much easier to get past the songs’ often overt racism and reflect more thoughtfully and deeply on a dark period in American history.

Today’s playlist:

Girolamo de Simone, Shama (Die Schachtel)
Raymond Scott Quintet, Ectoplasm (Basta)
Hank Roberts, Green (Winter & Winter)
Chris Dench, Beyond Status Geometry (Tzadik)
Harold Melvin & the Blue Notes, Wake Up Everybody (Philadelphia International/Legacy)