Chalie Boy is a Southern rapper and singer from Central Texas who made his major-label debut in 2009 with the breakout hit single "I Look Good." Born Charles Williams in the vicinity of Calvert (the hometown of his father) and Hearne (the hometown of his mother), two small cities in Robertson County, Texas, he began singing in his church choir at the age of three and cites musical influences that include seminal rappers UGK, Run-D.M.C., and Grandmaster Flash & the Furious Five, as well as blues legends Bobby "Blue" Bland, B.B. King, and Johnnie Taylor.
As a rapper, he joined the stable of Dirty 3rd Records in 2000 and initially established himself on the mixtape scene as a member of the Freestyle Kingz. Full-length solo efforts such as Making My Way (2004) and Versatyle Child (2006) paved the way for a major-label recording deal with Battery/Jive. His first single, "I Feel Good," was first popular on the Houston radio station KBXX and the Dallas stations KBFB and KKDA before getting nationwide airplay. As the song became a breakout hit for Chalie Boy, a remix was released featuring well-known Southern rappers Slim Thug, Juvenile, and Bun B. The song eventually peaked at number 20 on Billboard's Hot R&B/Hip-Hop Songs chart.
Although Chalie Boy didn't release an album for Jive, he maintained a steady mixtape release schedule with independent titles like Life of an Entertainer (2010), a third volume in his Versatyle Child series (2011), and Chalie (2014).