Bobby McFerrin vs. George H.W. Bush
Song: "Don't Worry, Be Happy"
Controversy: The VP used the a cappella chart-topper as his presidential campaign theme, but McFerrin was a Dukakis supporter, and asked team Bush to stop. The Republican candidate went on a charm offensive, telling McFerrin he loved the song and inviting him to dinner, but the singer was unmoved. To drive home the point, he even stopped performing the song for a while.
Result: The Bush campaign dropped the tune, and "This Land Is Your Land" by Woody Guthrie became its official song instead.