A native of Phoenix, Arizona, Flemons grew up listening to his parents' vintage R&B collection. A gifted guitarist and harmonica player by his teens, he quickly expanded his musical boundaries, listening to artists like Bob Dylan, the Beatles, and Chuck Berry, as well as seeking out such early progenitors of American roots music as Woody Guthrie, Tom Paxton, and Jack Elliott. After high school, Flemons attended Northern Arizona University in Flagstaff, where he played locally, often busking on the street. It was while in Flagstaff that he came into contact with veteran percussionist, banjo player, and folklorist Sule Greg Wilson, a local musical oracle who had played with everyone from famed Nigerian percussionist Babatunde Olatunji to such legendary Piedmont blues artists as fiddler Joe Thompson and guitarist/vocalist Algia Mae Hinton. Wilson became a mentor to Flemons and helped him develop his playing and historical understanding of blues and folk music.
In 2005, at Wilson's behest, Flemons attended the Black Banjo Gathering, a four-day festival celebrating the African, Afro-Caribbean, and African-American origins of banjo music. During the gathering, Flemons befriended fellow roots music enthusiasts vocalist/banjo player Rhiannon Giddens and vocalist/violinist Justin Robinson. Inspired by their festival experiences, the trio formed the Carolina Chocolate Drops and released several highly acclaimed albums including 2006's Dona Got a Ramblin' Mind, 2010's Genuine Negro Jig, and 2012's Leaving Eden, among others. As a solo artist, Flemons continued to perform and record, debuting in 2007 with Dance Tunes Ballads Blues. In addition to producing a number of other artists, he also released a collaborative album with guitarist Boo Hanks called Buffalo Junction. After amicably parting ways with the Carolina Chocolate Drops in 2012, Flemons refocused on his solo work, releasing the album Prospect Hill on Fat Possum in 2014. The next couple of years saw him building his reputation as popular touring act, landing prestigious gigs at Carnegie Hall as part of a Lead Belly tribute and at the opening ceremonies for the National Museum of African American History and Culture in Washington, D.C. In 2016, Flemons joined legendary British guitarist Martin Simpson on the album Selection of Ever Popular Favourites. His 2018 album, Black Cowboys, was released as part of Smithsonian Folkways' African-American Legacy Recordings series and unearthed material pertaining to African Americans' role as pioneers of the West. 2020 saw an expanded reissue of Flemons' Prospect Hill album that included the rare What Got Over EP and a selection of instrumentals. ~ Matt Collar, Rovi