"Open Your Heart" began life as a rock song titled "Follow Your Heart" intended for Cyndi Lauper. However, after Madonna helped re-orient it as a dance-pop track, "Open Your Heart" became the fourth single from the album True Blue and ultimately went all the way to #1. The music video generated both acclaim and criticism with its depiction of Madonna as a peepshow dancer befriending a young boy.
"La Isla Bonita" was released in February 1987 as the fifth single from True Blue. It was the first of Madonna's top 10 singles to incorporate a Latin feel. The song was first offered to Michael Jackson. Madonna worked with Patrick Leonard to re-write some of the lyrics and "La Isla Bonita" became another top 5 pop hit. The accompanying video included an appearance by actor Benicio del Toro.
"Who's That Girl" is the title song from the movie starring Madonna. The film did poorly both critically and financially, but that did not hurt the fortunes of the song. It continued Madonna's interest in Latin and Spanish influences incorporating Spanish lyrics. "Who's That Girl" became Madonna's sixth #1 hit single, and she became the first woman to have six #1 hits as a solo artist.
"Causing a Commotion" was released in August 1987 as the second single from the Who's That Girl soundtrack. The song was co-written and co-produced by Stephen Bray and an acclaimed remix was released by Shep Pettibone. "Causing a Commotion" peaked at #2 on the pop singles chart kept out of the top spot by Michael Jackson's "Bad."
More than a year passed before the release of Madonna's next single. When it did appear in February 1989, the single "Like a Prayer" was acclaimed as a stunning achievement. It went straight to the top of the pop singles chart and is often cited as the top song of Madonna's career. The arresting video created by Mary Lambert to accompany "Like a Prayer" intensified tension between Madonna and the Roman Catholic Church. Among the images that appear are Madonna with stigmata, suggestion of making love to an iconic saint, and burning crosses.
Madonna made her support for empowerment of women absolutely clear with the release of the song "Express Yourself." Future film director David Fincher put together the promotional video for "Express Yourself" utilizing imagery inspired by the classic silent film Metropolis. With a budget of $5 million it was the most expensive music video made up to that point in time. "Express Yourself" is frequently hailed as one of the top music videos of all time.
"Cherish" was released in August 1989 as the third single from the Like a Prayer album. It has a distinctly lighter feel from the album's two previous singles. The accompanying music video is in black and white and directed by fashion photographer Herb Ritts. It includes an appearance by model Tony Ward, a former lover of Madonna's who also made a notable appearance in the video for "Justify My Love." "Cherish" was Madonna's record-setting 16th consecutive top 5 hit.
Madonna began the 1990's by missing the top 5 of the pop singles chart for the first time since 1984. Her single "Oh Father" failed to even make it to the top 10. "Keep It Together" was released as the fifth single from the Like a Prayer album and returned Madonna to the top 10. "Keep It Together" lyrically is an inspirational and impassioned tribute to the importance of family and supporting those who are close to you. It was the final collaboration with songwriter and producer Stephen Bray released as a single.
Reportedly created as a hurried B-side for the "Keep It Together" single by Madonna and dance music producer and remixer Shep Pettibone, "Vogue" was presented to record company executives and they decided to hold it back as its own single release. Released in March 1990, the song is partly inspired by a style of dancing called vogueing common in the gay underground in New York. David Fincher put together a black and white old Hollywood style video to accompany the single, and "Vogue" became Madonna's biggest worldwide success to date topping the charts in over 30 countries.
"Hanky Panky" was the key single release from the soundtrack to the film Dick Tracy starring Madonna and Warren Beatty. It generated controversy with its racy lyrics and Madonna's statement that the song is, "about a spanking, but not the kind that you get when you're bad."