In spite of his handicap, he overcame the odds by becoming a top-form bluesman, singing with a gritty, passionate vocal style and playing a mean bottleneck slide guitar. According to legend he was also quite adept with a pistol -- being able to judge the position of a target by sound alone -- and traveled across the country under a slew of aliases, as a means of avoiding the police. He was jailed at least two times.
As a recording artist, Reynolds began in 1929, after he was discovered by blues talent scout H.C. Speir. Reynolds visited Paramount Records in Grafton, Wisconsin on two occasions -- recording two sides per session. The four resulting sides, “Cold Woman Blues,” “Nehi Blues,” “Ninety Nine Blues,” and “Outside Woman Blues” are downright haunting and legendary. The last of these four sides, “Outside Woman Blues'' would go on to be covered by 1960s psychedelic rock band Cream on their second album, “Disraeli Gears.” “Cold Woman Blues/Ninety Nine Blues” were lost until 1976, when it was purchased at a flea market for one dollar. It was later resold for an undisclosed amount in 2000; it is, to date, the only known copy of the record in existence. In 1930, Reynolds would cut four more sides for Victor Records...those being “Goose Hill Woman Blues,” Short Dress Blues,” “Married Man Blues,” and “Third Street Woman Blues.” The first two of these sides are thought to be lost entirely; they have not been found to this day.
On March 10, 1968, Reynolds died of a stroke in a Monroe, Louisiana hospital. His artistry in blues, as exemplified by his visceral country blues style has withstood the test of time, proving to be just as powerful well into the 21st century.