Beginning in 1995, Madonna began one of her most subtle image makeovers as she lobbied for the title role in the film adaptation of Andrew Lloyd Webber's Evita. Backing away from the overt sexuality of Erotica and Bedtime Stories, Madonna recast herself as an upscale sophisticate, and the compilation Something to Remember fit into the plan nicely. Released in the fall of 1995, around the same time she won the coveted role of Evita Peron, the album was comprised entirely of ballads, designed to appeal to the mature audience that would also be the target of Evita. As the filming completed, Madonna announced she was pregnant and her daughter, Lourdes, was born late in 1996, just as Evita was scheduled for release. The movie was greeted with generally positive reviews and Madonna began a campaign for an Oscar nomination that resulted in her winning the Golden Globe for Best Actress (Musical or Comedy), but not the coveted Academy Award nomination. The soundtrack for Evita, however, was a modest hit, with a dance remix of "Don't Cry for Me Argentina" and the newly written "You Must Love Me" both becoming hits.

During 1997, she worked with producer William Orbit on her first album of new material since 1994's Bedtime Stories. The resulting record, Ray of Light, was heavily influenced by electronica, techno, and trip-hop, thereby updating her classic dance-pop sound for the late '90s. Ray of Light received uniformly excellent reviews upon its March 1998 release and debuted at number two on the charts. Within a month, the record was shaping up to be her biggest album since Like a Prayer. Two years later she returned with Music, which reunited her with Orbit and also featured production work from Mark "Spike" Stent and Mirwais, a French electro-pop producer/musician in the vein of Daft Punk and Air.

The year 2000 also saw the birth of Madonna's second child, Rocco, whom she had with filmmaker Guy Ritchie; the two married at the very end of the year. With Ritchie as director and Madonna as star, the pair released a remake of the film Swept Away in 2002. It tanked at the box office, failing to crack seven digits, making it one of the least profitable films of the year. Her sober 2003 album, American Life, fared slightly better but was hardly a huge success. That same year also saw the release of Madonna's successful children's book, -The English Roses, which was followed by several more novels in future years. Confessions on a Dance Floor marked her return to music, specifically to the dance-oriented material that had made her a star. Released in late 2005, it topped the Billboard charts and was accompanied by a worldwide tour in 2006, the same year that I'm Going to Tell You a Secret, a CD/DVD made during her Re-Invention Tour, came out. In 2007, Madonna released another CD/DVD, Confessions Tour, this time chronicling her controversial tour of the same name. She then inched closer to the completion of her Warner Bros contract with 2008's Hard Candy, an R&B album whose first single, "4 Minutes", topped the singles charts in several countries. ~ Stephen Thomas Erlewine, All Music Guide