Dawayne Bailey is an American guitarist who has toured and recorded with Bob Seger & the Silver Bullet Band, Véronique Sanson, and Chicago.
While still attending Manhattan High School in Kansas, he founded the band Rathbone, which developed a strong regional fan base.
It was during this time that Bailey's former bandmate Jason Scheff called him to audition for the lead guitarist spot in Chicago.
Bailey toured and recorded with Chicago from July 1986 to January 1995, and was a contributor to their previously unreleased album, which was intended in 1994 to be titled Stone of Sisyphus.
The latter was not included on the eventual June 2008 Rhino Records release of Chicago XXXII: Stone of Sisyphus for unknown reasons.