“America’s reigning pop princess has a firm grip on fame, fortune and, more important, reality.” At least that’s how it looked the last time Glamour profiled Britney Spears, in December 2003, when we named her one of our Women of the Year. Back then, the 22-year-old was a certified pop music powerhouse. With her most recent CD perched on top of the charts, she’d already sold 28 million albums in the United States alone, was pulling in a staggering $39 million a year and had created an arts immersion camp for underprivileged children.

And then the trouble began. Over the past five years, our hearts have broken again and again for Spears. No, not because of her career (she continues to be a hit-making machine), but because of everything else. To recap: two failed marriages, a custody battle and what seemed like a slow-motion breakdown. In 2006 she called herself an “emotional wreck” in an interview with Matt Lauer, then flashed the entire world in numerous no-underwear paparazzi shots. In 2007 she stunned us by shaving her head for the cameras, made several visits to rehab and attacked a photographer’s car with—remember this?—a green umbrella. She attempted a sexy “See, I’m OK” performance on the VMAs that September,only to be ravaged by critics and fans for her drowsy dancing and off-time lip-synching. Her peers went public with their concern: “She can call me and come live in our house with us for a couple of months,” Heidi Klum said in a show of support. “I would help set her straight.”

Of course it wasn’t that easy. Within a month, Spears was charged with a misdemeanor hit-and-run and lost custody of her kids to K-Fed. Then, on January 3, 2008, the pop star was carried out of her L.A. home on a gurney and whisked to Cedars-Sinai Medical Center. Her diagnosis was widely rumored to be bipolar disorder, but her mother, Lynne Spears, has a different opinion. “I believe Britney had postpartum depression, which [in addition to]…the end of her marriage to Kevin and the enormous pressures of her career, brought her to the breaking point,” Lynne claims in her tell-all book, Through the Storm. “Something inside of her had broken and needed to be healed.”

Spears was released January 5 but hospitalized again within a few weeks. (That ambulance ride was attended by a dozen motorcycle officers, a pair of police cruisers and two helicopters.) The next day, while she was in a psychiatric ward, her father, Jamie Spears, signed documents in a Los Angeles court that stated his daughter was “in an immediate and substantial medical emergency.” He then became her court-appointed temporary conservator, with a say in her medical care and control over her financial and personal decisions.