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Duck was born Jimmy Charles Holmes on July 28, 1947 in Bentonia, Mississippi to Carey and Mary Holmes. His parents opened the Blue Front Cafe in 1948. Duck took over the cafe in 1970. After taking ownership, he encouraged Jack Owens and Bud Spires to play there more often. Duck was taught the Bentonia style of playing by Henry Stuckey, the originator of the style. With encouragement from Jack and Bud, he honed his style to become one of the leading practitioners of the style. Duck's first recording date to the late 1970s when he recorded "Devil's Blues" with Cornelius Bright for David Evans. In the 1980s, he began appearing at the Bentonia Blues Festival which had begun as a community event started by his mother, Mary, and grew into one of the longest running blues festival in America. In 2003, recorded his first album at Pluto Plantation for Shade Tree Records, though the company would fold without ever releasing the recording. In 2005, Jeff Konkel would visit the Blue Front Cafe and record Duck and these recordings would be released in 2006 as Back to Bentonia. The album would win to Living Blues awards for Duck. In 2007, he followed up with the album, Done Got Tired of Tryin'. The album received critical acclaim and was named by WXPN, World Cafe as one of the top ten albums of the year and was also nominated for a Blues Music Award.