1992–1997: Maverick, Erotica, Sex, Bedtime Stories, Evita, and motherhood
In 1992, Madonna appeared in the film A League of Their Own as a member of an all-women's baseball team. The film reached number one at the US box office in its second weekend of release. Madonna also recorded its theme song, "This Used to Be My Playground", which became her tenth Billboard Hot 100 number-one single, the most for a woman at the time. In April 1992, Madonna established the entertainment company Maverick, which included a record label, film production unit, and divisions for music publishing, television, book publishing, and merchandising. The venture was a partnership with Time Warner and provided her with a $60 million advance and a 20 percent royalty rate—the highest in the industry at the time. Maverick went on to become one of the most successful artist-run labels in history, signing successful acts such as Alanis Morissette and Michelle Branch.
Later in 1992, Madonna co-sponsored the first museum retrospective of her former partner, artist Jean-Michel Basquiat, at the Whitney Museum of American Art in New York. She released her fifth studio album, Erotica, on October 20, 1992, in the US, and published her coffee table book Sex a day later. Sex featured sexually provocative and explicit images photographed by Steven Meisel and drew strong negative reactions from critics, the general public, and conservative, feminist and anti-porn groups; initial interest propelled the book to the top of The New York Times Best Seller list. A writer from The Washington Post described it as an "oversized, overpriced, [and boring] coffee table book of hardcore sexual fantasies".
The widespread backlash overshadowed Erotica, which became her lowest-selling album at the time. It reached number two on the US Billboard 200, and received favorable reviews from critics. The singles "Erotica" and "Deeper and Deeper" reached the top ten of the Billboard Hot 100 and number one in Italy. During this period, Madonna was in a relationship with rapper Vanilla Ice, to whom she proposed. The pair separated following the release of Sex, with Vanilla Ice claiming he had been included in the book without his consent. Her performances in the 1993 films Body of Evidence and Dangerous Game were poorly received. The former featured scenes of sadomasochism and bondage, while she played the abused wife of a filmmaker in the latter.
Madonna launched her fourth concert tour, the Girlie Show, in September 1993, during which she appeared as a whip-cracking dominatrix and performed alongside topless dancers. She made a highly publicized appearance on the Late Show with David Letterman in March 1994, using profanity that required broadcast censorship and handing Letterman a pair of her underwear while urging him to smell it. The sexually explicit releases of Sex and Erotica, along with her film roles and controversial Letterman appearance, prompted commentators to question her dependence on provocative imagery. Madonna briefly dated rapper Tupac Shakur and basketball player Dennis Rodman around this time. Biographer J. Randy Taraborrelli viewed Madonna's ballad "I'll Remember"—recorded for the film With Honors (1994)—as an effort to soften her provocative image. It peaked at number two on the Billboard Hot 100.
With her sixth studio album, Bedtime Stories, Madonna embraced a gentler sound and image to regain public favor. Released in the US on October 25, 1994, the album debuted at number three on the Billboard 200 and produced the singles "Secret" and "Take a Bow", which peaked at numbers three and one on the Billboard Hot 100, respectively. "Take a Bow" spent seven weeks atop the chart, making it her longest-running number-one. Madonna sponsored the first major retrospective of Tina Modotti's work at the Philadelphia Museum of Art in 1995, and later supported exhibitions of Basquiat's paintings at London's Serpentine Gallery and Cindy Sherman at New York's Museum of Modern Art. In November 1995, Madonna released Something to Remember, a compilation album that comprises Madonna's ballads across the past decade. The record debuted at number six on the Billboard 200 and has sold ten million copies worldwide.
In February 1996, Madonna began filming the musical Evita in Argentina. Having long aspired to portray Argentine political leader Eva Perón, she wrote to director Alan Parker to express her interest in the role. After being cast, she undertook vocal training and studied Argentina's history and Perón's life. During production, Madonna experienced several bouts of illness related to pregnancy and the emotional demands of the film. Upon its release in December 1996, her performance was met with positive reviews from critics. Richard Corliss, writing for Time, described the film as well cast and visually impressive, lauding Madonna's ability to exceed expectations. Her portrayal earned her the Golden Globe Award for Best Actress in a Motion Picture – Musical or Comedy.
The Evita soundtrack, which peaked at number two on the Billboard 200, contained songs primarily performed by Madonna. These included "You Must Love Me" and "Don't Cry for Me Argentina", the latter of which topped the European singles chart. On October 14, 1996, she gave birth to her daughter, Lourdes "Lola" Maria Ciccone Leon, with fitness trainer Carlos Leon. According to biographer Mary Cross, Madonna—who had expressed concern that her pregnancy might jeopardize Evita—fulfilled significant personal goals: "Madonna had at last triumphed on screen and achieved her dream of having a child, both in the same year [...] reinventing herself and her image with the public". Her relationship with Carlos ended in May 1997, and she stated that they were "better off as best friends".