Video of Madonna

1986–1991: True Blue, Who's That Girl, and Like a Prayer

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 resulted in three singles making it to number-one 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, and became her best-selling studio album of her career to this date with sales of 25 million. In the same year, Madonna starred in the critically panned film Shanghai Surprise, for which she received her first Golden Raspberry Award for Worst Actress. She made her theatrical debut in a production of David Rabe's Goose and Tom-Tom; the film and play both co-starred Penn. The next year, Madonna was featured in the film Who's That Girl. She contributed four songs to its soundtrack, including the title track and "Causing a Commotion".

Madonna embarked on the Who's That Girl World Tour in July 1987, which continued until September. It broke several attendance records, including over 130,000 audience in a concert near Paris, which remains her biggest concert attendance ever. Later that year, she released a remix album of past hits, titled You Can Dance, which reached number 14 on the Billboard 200. After an annulment in December 1987, Madonna filed for divorce from Penn in January 1989, citing irreconcilable differences.

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 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. 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. Madonna received positive feedback for the album, with Rolling Stone writing that it was "as close to art as pop music gets". Like a Prayer peaked at number one on the Billboard 200 and sold 15 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 MTV, Billboard and Musician magazine.

Madonna starred as Breathless Mahoney in the film Dick Tracy (1990), with Warren Beatty playing the title role. Her performance led to 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 U.S. number-one song "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, Madonna began her Blond Ambition World Tour, which was held until 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 Laserdisc release of the tour won Madonna a Grammy Award in 1992 for Best Long Form Music Video.

The Immaculate Collection, Madonna's first greatest-hits compilation album, was released in November 1990. It included 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 U.S. and top ten worldwide. Its music video 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. Madonna responded to the banning: "Why is it that people are willing to go and watch a movie about someone getting blown to bits for no reason at all, and nobody wants to see two girls kissing and two men snuggling?"

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. Around this time, Madonna had an eight-month relationship with rapper Vanilla Ice; he ended their relationship because of Madonna's Sex book. Her first documentary film Truth or Dare (known as In Bed with Madonna outside North America) was released in May 1991. The documentary chronicled her Blond Ambition World Tour.