11. "Like a Prayer" (1989)
"Like a Prayer," with its dramatic lyrics and gospel choir backup, is undoubtedly one of Madonna's biggest hits of all time. But the video, complete with burning crosses and Madonna making out with a black saint, was just a tad controversial.
Pepsi had signed a deal to use Madonna and the song for a soda commercial, but they backed out when they saw the scandalous video. Still, the song topped the charts in every major music market in the world, and the video won an MTV Viewers Choice Award, sponsored by -- you guessed it -- Pepsi!
12. "Express Yourself" (1989)
A call to women everywhere to stick up for what they want, "Express Yourself" was a top-five hit around the world, peaking at number two in the States. The notorious conical bra made its debut in the video. Designed by Jean-Paul Gautier, the pink corset with the pointy cups was worn under a black suit in the video and throughout Madonna's Blonde Ambition Tour as well.
13. "Cherish" (1989)
The third hit single off the Like a Prayer juggernaut, "Cherish" is a song that finds Madonna in an innocent frame of mind, singing about the joys of true love. The song reached number two in the States, her seventeenth single to reach the top ten on U.S. charts.