In June 1986, Madonna released her third studio album, True Blue, which was inspired by and dedicated to Sean Penn. Rolling Stone magazine was generally impressed with the effort, writing that the album "sound[s] as if it comes from the heart".It spawned three number one singles on the Billboard Hot 100: "Live to Tell", "Papa Don't Preach" and "Open Your Heart", and two more top-five singles: "True Blue" and "La Isla Bonita". The album topped the charts in over 28 countries worldwide, an unprecedented achievement at the time. She also starred in the critically panned film Shanghai Surprise, and made her theatrical debut in a production of David Rabe's Goose and Tom-Tom, both co-starring Penn. The next year, Madonna's second feature film Who's That Girl was released. She contributed four songs to its soundtrack, including the title track and "Causing a Commotion". In June 1987, she embarked on the Who's That Girl World Tour which continued until September. Regarding the tour, Madonna commented "I realised that I could go from being unmoulded clay, and over time and with the help of people, I could turn myself into something else. This tour is the reflection of that belief and it's as if saying to me 'Who are you girl?' Hence the name, its the new me." Later that year, she released a remix album of past hits, entitled You Can Dance, which reached 14 on the Billboard 200.Madonna and Penn filed for divorce in December 1987, citing irreconcilable differences, with Madonna's lawyer pointing to Penn's drinking problem and his abusive nature. The divorce was finalized in January 1989. Of her marriage to Penn, Madonna later said, "I was completely obsessed with my career and not ready to be generous in any shape or form."
"In Like a Prayer I've been dealing with more specific issues that mean a lot to me. They're about an assimilation of experiences I've had in my life and in relationships. They're about my mother, my father and my bonds with my family about the pain of dying, or growing up and letting go. [The album] was a real coming-of-age record for me emotionally. I had to do a lot of soul-searching and I think it is a reflection of that."
—Madonna talking about the inspiration behind Like a Prayer.
In January 1989, Madonna signed an endorsement deal with soft drink manufacturer Pepsi. In one of her Pepsi commercials, she debuted her song "Like a Prayer". The corresponding music video featured many Catholic symbols such as stigmata and burning crosses, and a dream about 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. However, she was allowed to retain her fee of five million dollars.The song was included on Madonna's fourth studio album, Like a Prayer, which was co-written and co-produced by Patrick Leonard and Stephen Bray. Rolling Stone hailed it as "...as close to art as pop music gets". Like a Prayer peaked at number one on the Billboard 200 and sold 13 million copies worldwide, with 4 million copies sold in the U.S. alone. Six singles were released from the album, including "Like a Prayer", which reached number-one, and "Express Yourself" and "Cherish", both peaking at number two. By the end of the 1980s, Madonna was named as the "Artist of the Decade" by media such as MTV, Billboard and Musician magazine.
Madonna starred as "Breathless" Mahoney in the film Dick Tracy (1990), with Warren Beatty playing the title role. 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 U.S. number one hit, "Vogue", and "Sooner or Later", which earned songwriter Stephen Sondheim an Academy Award for Best Original Song in 1991. While shooting the film, Madonna began a relationship with Beatty which dissolved by the end of 1990. In April 1990 she began her Blond Ambition World Tour, which continued for nearly four months. Regarding the tour, Madonna commented "I know that I'm not the best singer and I know that I'm not the best dancer. But, I can fucking push people's buttons and be as provocative as I want. The tour's goal is to break useless taboos." Rolling Stone called it an "elaborately choreographed, sexually provocative extravaganza" and proclaimed it "the best tour of 1990". The tour was met with strong reaction from religious groups for her performance of "Like a Virgin", during which two male dancers caressed her body before she simulated masturbation.The Pope asked the general public and the Christian community not to attend the concert. A private association of Catholics calling themselves Famiglia Domani also boycotted the tour for its eroticism. In response, Madonna said, "I am Italian American and proud of it. 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"; she declared that the Church "completely frowns on sex ... except for procreation." The Laserdisc release of the tour won Madonna a Grammy Award in 1992 for Best Long Form Music Video.
In December 1990, Madonna decided to leave Jennifer Lynch's film Boxing Helena, which she had previously agreed to star in, without any explanation to the producers. From late 1990 to early 1991, Madonna dated Tony Ward, a model and pornography performer who appeared in her music videos for "Cherish" and "Justify My Love". She also had an eight-month relationship with rapper Vanilla Ice. Her first documentary film Truth or Dare (known as In Bed with Madonna outside North America) was released in mid-1991. The documentary chronicled her Blond Ambition World Tour and provided glimpses into her personal life.
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