May 1989: Madonna Releases EXPRESS YOURSELF

By the spring of 1989, Madonna was among the biggest pop stars on the planet. The singer had turned up the heat considerably with the release of "Like a Prayer," the lead single and title track of her fourth studio album. The song generated a whirlwind of controversy with the release of the Mary Lambert-directed music video, which challenged racism with eye-popping imagery including burning crosses and Madonna kissing black actor, Leon Robinson, in a depiction of interracial romance. The divisive video was so hot that Pepsi decided to pull a massive advertising campaign that featured the singer and the song. Even the Vatican felt the need to decry the video's release.

So when it came time for Madonna to release a second single and video from Like a Prayer, she turned to longtime collaborator, Stephen Bray, and the song "Express Yourself." Madonna and Bray had much history together, having dated the singer during her time at University of Michigan in Ann Arbor, who eventually moved to New York and started the band Breakfast Club, which featured Madonna playing drums. "Express Yourself" was the first song Bray and Madonna worked on for her fourth full-length project. They penned the song as a tribute to late '60s/'70s funk-rock legends Sly and the Family Stone.

The song also signified Madonna's desire to write music more reflective of her own maturation as a woman and an artist.The strong female empowerment message found in "Express Yourself" was borne in part from the artist's divorce from first husband, actor Sean Penn, in January 1989.

"The ultimate thing behind the song is that if you don't express yourself, if you don't say what you want, then you're not going to get it," Madonna told writer Mick St. Michael in the book Madonna 'Talking': Madonna in Her Own Words. "And in effect you are chained down by your inability to say what you feel or go after what you want."

Released as a single on May 9, 1989, "Express Yourself" charged up the charts to peak at #2 on the Billboard Hot 100 for the week of July 15, 1989. The song that blocked Madonna and "Express Yourself" from #1? Simply Red with "If You Don't Know Me by Now."

Helping the power the song over the airwaves and up the charts was a splashy and big-budget music video (the most expensive clip at the time), directed by David Fincher. Inspired by Fritz Lang’s dystopian film Metropolis, the clip delighted viewers with its big, bold visuals of Madonna as the ultimate power broker, complete with her own toy-boy, model Cameron Alborzian.

“Madonna likes to play, so it made things a lot more fun,” Alborzian told EW in 2017 in regards to their steamy nude scene in the clip. “She was probably more naked than she needed to be.”

Alborzian recalled the overall vibe being fun and friendly throughout the video, despite long and late-night hours: “[Madonna’s then boyfriend] Warren Beatty was there, Herb Ritts was there, it was just an amazing time. We hung out in each other’s trailers and she was very positive about life, just living it up.”