Soon the virgin gave way to the sexual provocateur. Jacobs says this period from the late '80s to the early '90s was his favorite. "She came into her own," he said. "She wasn't just a sex symbol, she was sexually provocative."
A defining image of that time was Madonna dressed in an exaggerated conelike bra designed by Jean-Paul Gaultier for her "Blond Ambition" tour. "That was her most iconic look," Parmenter said. "No one else was wearing massive conical bras. It was completely different."
Madonna also allowed a camera to follow her on tour and turned it into the hugely successful documentary "Truth or Dare." "It felt like she was showing you her private life," Parmenter said.
But the real reveal was yet to come, with her 1992 book "Sex," which accompanied her fifth studio album, "Erotica." The soft-core pornographic photos, which included simulations of homosexuality and sadomasochism and later turned up in Madonna's video for the album's title song, drew heaps of controversy. In a now-famous interview with "Nightline," Madonna defended her actions.
It didn't matter. All 1.5 million copies of the book's first edition sold out worldwide in the first week, making "Sex" one of the most successful coffee-table books ever released.
"It's a very collectible piece," said Parmenter.
Don't Cry for Me
In 1996, Madonna switched gears again, this time taking the lead role as Eva Peron, the popular wife of Argentinean dictator Juan Peron, in the musical film "Evita." Though she appeared in several films, it was her first major role and her most acclaimed -- she won a Golden Globe for her performance.
"'Evita' was definitely much more of a serious phase," Parmenter said. "She got proper vocal training for that, moved to London to record the soundtrack. I think it was her best performance. It's like one big continuous pop video."
Jacobs believes Madonna is frustrated that her film career hasn't been bigger. "I think she'll continue to push on that front," he said.
Madonna Becomes a Mom and Sees the Light
After "Evita," Madonna dropped out of sight for a while and gave birth to daughter Lourdes with trainer Carlos Leon. Her drive to become a mother is famous. She reportedly even considered Dennis Rodman as a baby-daddy at one point.
"One time I was in Las Vegas at the craps table doing my thing when I got this frantic call," Rodman wrote in his autobiography. "It was like the 'Somebody died call' from New York. I picked up the phone and Madonna was like, 'I'm ovulating, I'm ovulating. Get your ass up here.'"
When she re-emerged on the music scene, it was clear she was dabbling in a newfound spirituality. She produced the well-received "Ray of Light" album, performing in Hindu garb with henna tattoos or long gothlike black robes and black hair.
"It was a total shock," Parmenter said. "I never expected that from her. I turned on [the television] and there was Madonna. She'd turned into a kind of witch with the black hair and gothic clothing."
Lady of the Manor
After marrying British filmmaker Guy Ritchie in 2000, she turned into Lady Madonna, moving to the English countryside, writing children's books about tea roses and even bird hunting.
"She had the English country tweeds," Parmenter said. "She even started doing the bird shooting and was photographed with a shotgun slung over her shoulder. Maybe she's just enthusiastic about the English countryside."