In 1987, Chapman released his first album, "First Hand". The album included the song "Weak Days", which peaked at No. 2 on the Contemporary Christian Music chart. In 1988, he followed with his second album, "Real Life Conversations", which earned him four more hits, including the No. 1 song "His Eyes". The song, which was co-written by James Isaac Elliott, earned the Contemporary Recorded Song of the Year award from the Gospel Music Association in 1989. That year, he also won a GMA Award for Songwriter of the Year.