As a youngster he fashioned his first fiddle out of a goods box strung with horsehair. Honing his musical skills in his family band, he began performing as a teen alongside Knoxville performers Ted Bogan and Carl Martin in groups like the Tennessee Chocolate Drops and the Four Aces. Armstrong's groups were exceptions to the rule of the era which dictated that black performers perform only material from the segregated "race music catalogs"; their repertoire included not only old-time jigs, reels, waltzes, rags, and minstrel show favorites, but also current jazz, blues, and Tin Pan Alley hits.

In 1930, the Chocolate Drops made their radio debut and cut their first sides for the Vocalion label. During the Depression, the trio of Howard, Bogan, and Martin lived on the road, playing throughout the Appalachian circuit and appearing with a medicine show headed by one Dr. Leon D. Bondara. By the early '30s they found themselves in Chicago, regularly playing the city's Southside and Maxwell Street flea market area; living on tips left them in dire financial straits, however, and they soon began "pullin' doors" -- playing stores and taverns in the white immigrant areas, where the Italian, Polish, and German which Armstrong learned to speak as a child growing up in multi-ethnic La Follette, opened doors that most other black performers found barred.

By the end of the decade, the popularity of radio and the emergence of the jukebox brought Armstrong's professional playing days to a halt; however, during the '70s his few recordings were rediscovered by folk music scholars, and he reunited with Bogan and Martin to tour college campuses, coffeehouses, and festivals. After Martin's 1978 death, the surviving duo forged on, and in 1985 they became the subject of the feature documentary Louie Bluie, a film directed by Terry Zwigoff. The accompanying soundtrack also introduced Armstrong's music to new fans through its mix of new recordings and vintage sides dating back to the '30s.

Armstrong continued to perform well into the new millennium. He and his wife/manager Barbara Ward married 1996 and took up residency in her hometown of Boston. She was also the drummer of Armstrong's band. His solo album, Louie Bluie, won a W.C. Handy award from the Blues Foundation a year prior. On July 30, 2003, Armstrong died from complications after a heart attack he suffered in March. He was 94. ~ Jason Ankeny