On July 22 1989, Madonna’s Express Yourself reached #2 on the Billboard Hot 100 Singles Chart. Express Yourself was the first song that Madonna and producer Stephen Bray collaborated on for the Like a Prayer album.
“The message of the song is that people should always say what it is they want. The reason relationships don’t work is because they are afraid. That’s been my problem in all my relationships. I’m sure people see me as an outspoken person, and for the most part, if I want something I ask for it. But sometimes you feel that if you ask for too much or ask for the wrong thing from someone you care about that that person won’t like you. And so you censor yourself. I’ve been guilty of that in every meaningful relationship I’ve ever had. The time I learn how not to edit myself will be the time I consider myself a complete adult.”
—Madonna talking to Stephen Holden of The New York Times.
Today In Madonna History 
With Express Yourself, Madonna left behind her reckless youth! Her first truly-and daringly-adult song!
She got ripped off it should have went to number one. The video was off the charts one of the greatest of all time and sheps remix was on point as well.
I believe Toy Soldiers by Martika and She drives me Crazy by the Fine Young Cannibals blocked EY from the number 1 spot. Both artists now are forgotten, but I agree it should’ve hit the top. But, regardless, all six singles were top 20 hits. It’s the only album where i believe all the songs could’ve been singles except Contrition.