"Justify My Love" was released in November 1990 as the first single from Madonna's greatest hits project The Immaculate Collection. MTV banned the promotional video due to sexual content. This created an immediate rush to see the video. It was released for sale as a video single and became an immediate bestseller. ABC's TV news magazine Nightline aired the video in its entirety and invited Madonna on to discuss the controversy. Commercially "Justify My Love" became another #1 hit for Madonna.
The second single from the greatest hits project The Immaculate Collection was "Rescue Me." The song was co-written and co-produced by Shep Pettibone and generated none of the controversy that swirled around "Justify My Love." It was officially released in February 1991 and peaked at #9 on the Billboard Hot 100.
"This Used to Be My Playground" is a battle that was used as theme music for the movie A League Of Their Own which starred Tom Hanks, Geena Davis, Rosie O'Donnell and Madonna. It was recorded during sessions for the upcoming Erotica album. Released in June 1992, the song reached #1 on the Billboard Hot 100 in August to become Madonna's tenth #1 hit.
"Erotica" arrived as the first single and title song from Madonna's album Erotica in October 1992. A slightly altered version of the song titled "Erotic" was packaged with Madonna's controversial Sex book. The frank sexual content of the song caused Vatican City to ban Madonna from the state and remove her music from any radio stations that broadcast there. "Erotica" debuted at #13 on the Billboard Hot 100 but only managed to rise to #3 for its peak.
"Deeper and Deeper" was the second single from the Erotica album and a straightforward disco style song. It was co-produced and co-written with Shep Pettibone. The accompanying video is an homage to pop artist Andy Warhol and his films with Madonna's performance obviously owing a debt to Edie Sedgwick.
After two singles from Erotica failed to make the top 10, Madonna returned with the single "I'll Remember," a ballad and theme song for the movie With Honors, in March 1994. Madonna worked with her old collaborator Patrick Leonard in writing and producing the song. "I'll Remember" was prevented from reaching #1 by All-4-One's smash hit "I Swear."
"Take a Bow" was the second single from Madonna's Bedtime Stories album. It is a ballad co-written and co-produced by R&B star Babyface. The song reached the top of the charts and spent the longest at #1, seven weeks, of any of Madonna's hits. In addition to being her 11th #1 pop single, "Take a Bow" became Madonna's fifth adult contemporary #1.
"You'll See" was the first single released from Madonna's 1995 ballad compilation Something To Remember. The accompanying video was a sequel to the clip put together for "Take a Bow" featuring Madonna and a bullfighter. "You'll See" became a massive international hit peaking at #6 in the US.
Many eyebrows were raised when Madonna successfully lobbied for and received the lead role in the film version of the musical Evita about the life of Argentina's Eva Peron. Despite the concerns Madonna received mostly positive notices for her performance and she turned the musical's best known song "Don't Cry for Me Argentina" into a pop hit. Dance remixes aided in the song's success, and it became an international pop smash.