From 1985-87, she turned out a stream of irresistibly catchy hit singles. 'Crazy For You' was co-written by ex- Carpenters collaborator John Bettis, while she and Steve Bray wrote 'Into The Groove'. These were followed by 'Dress You Up' and 'Papa Don't Preach', with its message of generational rebellion. 'True Blue', 'Open Your Heart' and 'La Isla Bonita' were later successes. Like an increasing number of her songs, 'Who's That Girl' (1987) was tied-in to a film - in this instance, a poorly received comedy in which she starred with Sir John Mills. Madonna's film career had begun in 1980 with a minor role in the B movie A Certain Sacrifice before she starred in Desperately Seeking Susan (1985). In Shanghai Surprise (1986), Madonna appeared with Penn, from whom she separated in 1988. In that year, she also appeared on Broadway in the play Speed The Plow by David Mamet. Madonna continued to attract controversy when, in 1989, the video for 'Like A Prayer', with its links between religion and eroticism, was condemned by the Vatican and caused Pepsi-Cola to cancel a sponsorship deal with the star. The resulting publicity helped the album of the same title - co-produced with new collaborator Patrick Leonard - to become a global bestseller.
In 1990, her career reached a new peak of publicity and commercial success. She starred with Warren Beatty in the blockbuster film Dick Tracy, while the extravagant costumes and choreography of the Blond Ambition world tour were the apotheosis of Madonna's uninhibited mélange of sexuality, song, dance and religiosity. The tour was commemorated by a documentary film, Truth Or Dare On The Band Behind The Scenes, And In Bed With Madonna, released in 1991. Among the hits of the early 90s were 'Vogue', devoted to a short-lived dance craze, 'Justify My Love' (co-written with Lenny Kravitz) and 'Rescue Me', produced by Madonna and Shep Pettibone. Madonna's reputation as a strong businesswoman, in control of each aspect of her career, was confirmed in 1992 when she signed a multi-million dollar deal with the Time-Warner conglomerate, parent company of Sire. This guaranteed the release of albums, films and books created by her Maverick production company. The publication of her graphic and erotic book Sex put her back on top of the charts, though this time it was in the best-selling book lists. The book was an unprecedented success, selling out within hours and needing an immediate reprint. On Bedtime Stories she teamed up with Soul II Soul producer Nellee Hooper, who wrote the title track in conjunction with Björk. It was prefaced by the Top 10 performance of 'Secret', and boasted 11 tracks that combined, by her own description, pop, R&B, hip-hop and Madonna. In 1996 her need to shock had mellowed considerably with a credible movie portrayal of Eva Peron in Evita. Later that year she became 'with child' on 14 October with the birth of Lourdes Maria Ciccone Leon. She returned to music with 1998's Ray of Light, one of her finest recordings to date. Collaborating with dance producer William Orbit, Madonna positively revelled in a newfound musical freedom. Her voice had also matured into a rich and expressive instrument.