1. Madonna Kisses Britney Spears and Christina Aguilera (2003)
Nineteen years after Madonna's iconic "Like a Virgin" performance, the stage was set with a wedding cake once again — only this time there were three brides. Joining Madonna for a rendition of the track were Britney Spears and Christina Aguilera, both of whom were trying to break out of their teen-idol boxes by proving how they were not, in fact, that innocent. Madonna decided to help both of them in that department, giving them mouth-on-mouth kisses — although the Britney one was steamier, and would be later teased in the video for their collab "Me Against The Music."