Grigsby auditioned for the second season of American Idol where he sang "Overjoyed" by Stevie Wonder in the first semi-final group and was one of two contestants from the round to automatically advanced to the semi-finals.
On July 21, 2005, Grigsby released, Charles Grigsby, an EP self-titled consisting of six tracks. In 2008 he joined The Croonerz that performed in local venues across northeast Ohio. In September 2010, he then became the lead vocalist in Centric in the Hard Rock Cafe in Pattaya, Thailand.
On September 1, 2011, he released a music download single, "Headliner," from his upcoming new album and performed the song on WJW Fox 8 Cleveland News. A benefit concert featuring Grigsby was held at The First Church in Oberlin on September 11, 2011.