In November, 2005, the group members attended the first Black Banjo Gathering in Boone, North Carolina where the Carolina Chocolate Drops were formed by Rhiannon Diddens, Dom Flemons and Justin Robinson. They were formerly known as Sankofa Strings where the members were all in their twenties while fourth member Sule Wilson, who occasionally performed with the group, was a generation older.
The Carolina Chocolate Drops released their first album, Dona Got a Ramblin’ Mind in September, 2006 on the Music Maker label. Then they recorded the soundtrack to the film The Great Debaters, which was released in December 2007 on Atlantic Records. Their second album Heritage was released on the Dixiefrog label in February 2008 and a live album, Carolina Chocolate Drops & Joe Thomas, which was recorded at Merlefest in April 2008 was released in May 2009 on the Music Maker label. The group signed with Nonesuch Records and their third album, Genuine Negro Jig, was released in February 2010. This was followed by an EP, Luminescent Orchestrii, which was released in January 2011. In February 2012, the group released their forth album, Leaving Eden.
During 2012 the group was nominated for awards by the Chicago Black Theater Alliance for “Keep a Song in Your Soul: The Roots of Black Vaudeville”, written by Giddens’ sister, Lalenja Harrington and Sule Greg Wilson, and staged by the Old Town School of Folk Music in Chicago. The show told the story of the Great Migration through music and dance. That same year, a Carolina Chocolate Drops song, “Daughter’s Lament,” was featured on the soundtrack to The Hunger Games. The following year the Carolina Chocolate Drops has a song, “Day of Liberty,” on the double CD album Divided & United.
During their career the Carolina Chocolate Drops have opened for musicians such as Taj Mahal and Bob Dylan, performed on Mountain Stage, MerleFest, A Prairie Home Companion, FreshAir, BBC Radio, Bonnaroo Music Festival and made several appearance on the Grand Ole Opry.
The Carolina Chocolate Drops won a Grammy Award for Best Traditional Folk Album titled Genuine Negro Jig in 2012. They were nominated for the Duo/Group of the Year award from the American Music Association in 2010 and 2012 and a Grammy for Best Folk Album for Leaving Eden in 2013.