stylistic:style_transfer, quality:corruption, quality:correction, structural:scholar_edition
1988–1991: Like a Prayer, Dick Tracy, and Truth or Dare

She made her Broadway debut in the production of Speed-the-Plow at the Royale Theatre from May to August 1988. According to the Associated Press, Madonna filed an assault report against Penn after an alleged incident at their Malibu home during the New Year's weekend. Madonna filed for divorce on January 5, 1989, and the following week she reportedly asked that no criminal charges be pressed.

In January 1989, Madonna signed an endorsement deal with soft-drink manufacturer Pepsi. In one Pepsi commercial, she debuted " Like a Prayer ", the lead single and title track from her fourth studio album. The music video featured Catholic symbols such as stigmata and cross burning, and a dream of making love to a saint, leading the Vatican to condemn the video. Religious groups sought to ban the commercial and boycott Pepsi products. Pepsi revoked the commercial and canceled her sponsorship contract. "Like a Prayer" topped the charts in many countries, becoming her seventh number-one on the Hot 100.

Madonna co-wrote and co-produced the album Like a Prayer with Patrick Leonard, Stephen Bray, and Prince. Music critic J. D. Considine from Rolling Stone praised it "as close to art as pop music gets... proof not only that Madonna should be taken seriously as an artist but that hers is one of the most compelling voices of the Eighties." Like a Prayer peaked at number one on the Billboard 200 and sold 15 million copies worldwide. Other successful singles from the album were " Express Yourself " and " Cherish ", which both peaked at number two in the US, as well as the UK top-five " Dear Jessie " and the US top-ten " Keep It Together ". By the end of the 1980s, Madonna was named as the "Artist of the Decade" by MTV, Billboard and Musician magazine.

Madonna starred as Breathless Mahoney in the film Dick Tracy (1990), with Warren Beatty playing the title role. The film went to number one on the US box office for two weeks and Madonna received a Saturn Award nomination for Best Actress. To accompany the film, she released the soundtrack album, I'm Breathless, which included songs inspired by the film's 1930s setting. It also featured the US number-one song " Vogue " and " Sooner or Later ". While shooting the film, Madonna began a relationship with Beatty, which dissolved shortly after the premiere.

In April 1990, Madonna began her Blond Ambition World Tour, which ended in August. Rolling Stone called it an "elaborately choreographed, sexually provocative extravaganza" and proclaimed it "the best tour of 1990". The tour generated strong negative reaction from religious groups for her performance of "Like a Virgin", during which two male dancers caressed her body before she simulated masturbation. In response, Madonna said, "The tour in no way hurts anybody's sentiments. It's for open minds and gets them to see sexuality in a different way. Their own and others". The live recording of the tour won Madonna her first Grammy Award, in the category of Best Long Form Music Video. In October 1990, Madonna lent her voice to a Public Service Announcement (PSA) supporting Rock the Vote 's efforts in voter registration.

Madonna's first greatest-hits compilation album, The Immaculate Collection (1990), was released in November including two new songs, " Justify My Love " and " Rescue Me ". The album was certified diamond by RIAA and sold over 30 million copies worldwide, becoming the best-selling compilation album by a solo artist in history. "Justify My Love" reached number one in the US becoming her ninth number-one on the Hot 100. Her then-boyfriend model Tony Ward co-starred in the music video, which featured scenes of sadomasochism, bondage, same-sex kissing, and brief nudity. The video was deemed too sexually explicit for MTV and was banned from the network. Her first documentary film, Truth or Dare (known as In Bed with Madonna outside North America), was released in May 1991. Chronicling her Blond Ambition World Tour, it became the highest-grossing documentary of all time (surpassed eleven years later by Michael Moore 's Bowling for Columbine).