Two months after Pepsi signs Madonna to a $5 million multiyear endorsement deal, the company features her in a TV commercial. The following day "Like a Prayer", one of the singer's most controversial videos, debuts with images of her kissing a black saint and dancing in front of a field of burning crosses. Backlash from religious groups forces Pepsi to pull the campaign, but Madonna keeps the cash.
Madonna brings young district attorney John F. Kennedy Jr. to a party she throws for art-world types at younger brother Christopher Ciccone's downtown New York loft. Onlookers say Madonna spent most of the party cozying up to John, but that he left alone to dine with girlfriend Daryl Hannah.
Madonna stars as nightclub singer opposite Warren Beatty in Dick Tracy, and they begin a short-lived romance. She soon takes up with rapper Vanilla Ice and her interpretation of Stephen Sondheim's "Sooner or Later" on the Dick Tracy soundtrack wins an Oscar for Best Song. That October, Forbes celebrates Madonna as "America's Smartest Business Woman," estimating that she has earned $125 million between 1985 and 1990.
MTV bans Madonna's five-minute "Justify My Love" video, which features S&M, bondage, lesbian sex and rampant nudity. "I think the video is romantic and loving and has humor in it," Madonna tells the New York Times. "Why is it that people are willing to go to a movie and watch someone get blown to bits for no reason, and nobody wants to see two girls?"
Madonna and Michael Jackson walk the red carpet together on Oscar night – he in his gold-tipped cowboy boots and blinding diamond brooch and she, dazzling in a pearl-encrusted Bob Mackie gown and $20 million worth of Harry Winston diamonds. At the post-Oscar party, though, she makes a beeline for Beatty, and Jackson hangs with Diana Ross.
The black-and-white documentary Truth or Dare chronicles many intimate moments during her 1990 Blond Ambition tour and receives an R rating. Entertainment Weekly calls Madonna "a natural egomaniac whom stardom completes." Indeed, an exasperated Warren Beatty is captured on film exclaiming, "She doesn't want to live off-camera!"
Departing from her sexy persona, Madonna turns in an endearingly sweet performance in A League of Their Own, a box-office grand slam about baseball's first female professional league. Off-screen, she strikes a close friendship with costar Rosie O'Donnell.
Madonna celebrates her liberation from prevailing social mores with Sex, a book of erotic pictures of herself by fashion photographer Steven Meisel. It is a commercial success but causes a passing image problem. "My rebellion happened, instead of in my teens, when I was 30," Madonna later tells PEOPLE. "I just wanted to go, 'Don't tell me what to do just 'cause I'm a girl. Don't tell me I can't be sexual and intelligent at the same time.' "
Madonna, who was raised a strict Catholic, becomes an avid devotee of Kabbalah, a form of Jewish mysticism. She will later draw future husband Guy Ritchie and Demi Moore into the practice. "He understands there are laws of the universe one has to live their life by," she tells PEOPLE in 2004. "That's the glue that will hold us together."
Madonna gives birth to Lourdes Maria Ciccone Leon, her daughter with personal trainer Carlos Leon. "I've never seen her happier," Rosie O'Donnell tells PEOPLE. "Lola has helped her to become more grounded, to leave the star part behind." Her relationship with Lola's father, however, ends within a year of the baby's birth.
BIOGRAPHY (top to bottom): Buena Vista Pictures/EVERETT; Ron Galella/WireImage; Fitzroy Barrett/Retna; Robin Platzer/Getty; Richard Young/REX USA; RAMEY