Band: Starship
Song: Nothing's Gonna Stop Us Now
Film: Mannequin
Year: 1987
May not exactly be official music video montages but....
Artist: Aimee Mann
Song: Wise Up
Film: Magnolia
Year: 1999
Artist: Aimee Mann
Song: Save Me
Film: Magnolia
Year: 1999
Team America Montage; 2004