The Billboard Roll Call is a listing of regional artists who have charted a song on the Billboard Top 40 from 1955-2009. The introduction has additional information.
Dewayne Bailey grew up in Manhattan, Kan. He founded Rathbone, a regional band, and moved to Los Angeles in the early 1970s.
In the mid-1980s, Bailey joined Bob Seger and the Silver Bullet Band. In addition to touring, he played on Seger’s Like a Rock album in 1986.
After he left the Silver Bullet Band, Bailey formed a band with bassist Jason Scheff. That band released one album, after which Scheff left to join Chicago and invited Bailey to audition. Bailey got the gig and was a member from 1986 to 1995.
As either a member of the Silver Bullet Band and Chicago, Baily has charted five songs on the Billboard Hot 100. The Seger songs are American Storm and Like a Rock, both of which were Top 15 hits in 1986.
With Chicago, Bailey was on the last three singles the band charted in the Top 40: You Are Not Alone (#10 in 1989), What Kind of Man Would I Be? (#5 in 1989) and Chasin’ the Wind (#39 in 1991).
In 2007, Bailey was inducted into the Kansas Music Hall of Fame. He is still active as a writer and recording artist in Los Angeles.
In the video below, Bailey is on the left side of the stage (wearing a headband) and plays the lead guitar parts.