Reynolds is thought to have been born in Tallulah, Louisiana in 1904, although his death certificate stated his birthplace as Arkansas in 1900. He was blinded by a shotgun blast to the face in Louisiana in the mid-late 1920s, which resulted in the physical loss of his eyes. Despite this handicap, Blind Joe became known for his distinctive bottleneck style as well as his reported accuracy with a pistol, with which it is said he could judge the position of a target by sound alone. After years of travelling and performing on street corners, Reynolds was eventually discovered in 1929 by musical talent scout H.C. Speir and is known to have entered the studio at least twice, recording four songs on each occasion.
In November 1929, Speir took Reynolds to a small studio in Grafton, Wisconsin where he recorded the songs "Cold Woman Blues", "Nehi Blues", "Ninety Nine Blues" and "Outside Woman Blues". These were recorded under the name Blind Joe Reynolds and released as two 78rpm records by Paramount Records.
In November 1930, Reynolds entered the studio once again, this time in Memphis, Tennessee. There he recorded the songs "Goose Hill Woman Blues", "Married Man Blues", "Short Dress Blues" and "Third Street Woman Blues" under the name "Blind Willie Reynolds" for Victor Records. However, only two of these songs were released, on a single 78rpm record. The recordings of "Goose Hill Woman Blues" and "Short Dress Blues" are thought to be lost forever.
The song "Outside Woman Blues" would later find fame when it was recorded by Cream for their 1967 album, Disraeli Gears. The group became aware of the song after guitarist Eric Clapton heard it featured on a blues compilation album (Origin Jazz Library OJL-8). Curiously, on their version, Cream gave the writing credit to 'Arthur Reynolds'.
Reynolds' "Ninety Nine Blues"/"Cold Woman Blues" 78rpm recording for Paramount was thought to be lost until 2000 when a copy, which had been purchased in 1976 at a flea market for one dollar.
Reynolds is known to have been polyamorous, as is apparent from a number of his recordings. He was also known to be outspoken and flamboyant, often using his music as a medium to attack society. Blind Joe Reynolds was the nom de disque of a Louisiana street singer by the name of Joe Sheppard, who devised his false recording names primarily to keep one step ahead of the law. He was blinded in the mid-'20s during an altercation with another man who shot Reynolds in the face with a shotgun. Throughout his life, Reynolds was known throughout the South not only as a singer, but for his open disrespect for police and the legal system, his contempt for conventional morality, and his pursuit of trouble. His surviving recordings are characterized by Reynolds' shrieking, high-pitched vocals; his rolling, generous, and infectiously rhythmic slide work; and his lyrics, which tend to focus on unfaithful women. Throughout his career, Reynolds travelled the country performing under various aliases as a way of evading the police, as he had served two jail sentences in his early life, as well as "escaping [his] enemies. In March 1968, Reynolds was admitted to a hospital in Monroe, Louisiana following a stroke, where he died on March 10. The cause of death was pneumonia.