YEAR 1987 - 1989

At the beginning of 1987, she had her fifth number one single with "Open Your Heart," the third number one from True Blue alone. The title cut from the soundtrack of her third feature film, Who's That Girl?, was another chart-topping hit, although the film itself was another box office bomb. 1988 was a relatively quiet year for Madonna as she spent the first half of the year acting in David Mamet's +Speed the Plow on Broadway. In the meantime, she released the remix album You Can Dance. After withdrawing the divorce papers she filed at the beginning of 1988, she divorced Penn at the beginning of 1989.

Like a Prayer, released in the spring of 1989, was her most ambitious and far-reaching album, incorporating elements of pop, rock, and dance. It was another number one hit and launched the number one title track as well as "Express Yourself," "Cherish," and "Keep It Together," three more Top Ten hits. In April 1990, she began her massive Blonde Ambition tour, which ran throughout the entire year. "Vogue" became a number one hit in May, setting the stage for her co-starring role in Warren Beatty's Dick Tracy; it was her most successful film appearance since Desperately Seeking Susan. Madonna released a greatest-hits album, The Immaculate Collection, at the end of the year. It featured two new songs, including the number one single "Justify My Love," which sparked another controversy with its sexy video; the second new song, "Rescue Me," became the highest-debuting single by a female artist in U.S. chart history, entering the charts at number 15. Truth or Dare, a documentary of the Blonde Ambition tour, was released to positive reviews and strong ticket sales during the spring of 1991.