Christopher Cross (1980)
The most-maligned Grammy winner of the pre-Milli Vanilli era. Christopher Cross won five awards for his mega-mellow debut. "We're not the new Jimi Hendrix," he admitted to Rolling Stone. "We're just a commercial pop band. I used to apologize for pop music, but I don't anymore." Right on, C.C. Yet you can't step to the smooth-osity of "Ride Like the Wind" or "Sailing," and the man's greatest hit was yet to come: "Arthur's Theme (Best That You Can Do)," i.e., the one that goes, "When you get caught between the moon and New York City." For a year or so there, he was a one-man C+C Music Factory (who were nominated for this category once, as were Kris Kross). He came back last month to play Jimmy Kimmel Live, jamming on "Ride Like the Wind" with his fan, Ron Burgundy.