Even for Amy Winehouse, it was a dramatic chain of events: After fainting and being rushed to a hospital, Winehouse's father said her crack and cigarette smoking had so damaged her lungs, she was risking emphysema and death if she didn't clean up.
Yet Winehouse — famous for her rebellious anthem "Rehab" — was photographed with a cigarette dangling from her lips as she left the hospital.
It was a potent symbol of how Winehouse's troubles have multiplied since February, when she was enjoying the triumph of her young career.
There she was, before a worldwide audience, surrounded by family after winning a record-tying five Grammys for her album "Back to Black." True, the 23-year-old Brit couldn't make it to the Los Angeles show — she had finally entered a rehabilitation clinic. But the Grammys were still a brilliant achievement after months of reported drug use, attempts at rehab, canceled performances and erratic behavior.
Immediately after the Feb. 10 ceremony, there was talk of relaunching her American tour. "There was a sense that maybe she was going to turn it around and she was going to get it together and it was going to be a great feel-good story," said veteran music journalist Alan Light.
"We all have a walk in life," legendary singer Chaka Khan, herself a past user of drugs, said backstage after Winehouse's wins. "We have hard and difficult times and going through that chaos often leads to clarity."
But since being released from the hospital this week, the only thing that's gotten clearer is how deeply troubled Winehouse remains. Police have investigated her for an alleged assault and for drug use; she's been photographed looking particularly wan and disheveled, with pockmarks on her face and marks on her arms; videotapes have been released showing disturbing behavior, including one where she sang a song full of racial slurs. Her father was quoted as saying she had only "70 percent lung capacity."
While drugs and music have a long history together, Winehouse's problems are remarkable given their prominence in a relatively short career (she made her U.K. debut in 2003 and her U.S. debut last year).
"It's definitely been a rough time for her," said Rick Krim, an executive vice president at VH1. The channel will broadcast taped highlights of a Friday birthday concert for Nelson Mandela; Winehouse was due to perform at the London show.
Cole: ‘I don't think she deserved it’
If she makes it to the venue, it's not clear which Winehouse will show up — the sultry, forceful singer or the bumbling, unfocused person who arrived an hour late to a June concert in Portugal. The brief set was marked by her croaking voice, highlighting the damage that smoking can cause to any singer's instrument.
After her stunning Grammy wins back in February, while there were lots of good wishes for Winehouse, not everyone thought The Recording Academy's coronation was a positive moment. Past Grammy winner Natalie Cole — who had battled drug addiction years ago — was quoted as saying: "I don't think she deserved it. ... I think she needs to get her life together first, and then get the awards later."
Noted Light: "It certainly doesn't look like the Grammys helped in any way for her to get cleaned up or figure it out at all."
But he cautioned against tying up an artist's personal conduct with getting awards, a notion shared by Recording Academy President Neil Portnow.
"Creativity and great artistry is really the benchmark of our evaluation and for our membership's judgment of their fellow artist's musical work," he said.
"We're always hopeful that a positive experience in the Grammy process is beneficial and uplifting for artists, on many levels," he added, "but we also know the stark realities of the difficulties of addiction and addiction recovery, and I think it would be naive for anyone to think that one event, even as much as a milestone for what it was, would erase those elements and circumstances that lead to those kind of difficulties in the first place."
Winehouse, born to a pharmacist mother and taxi-driver father, grew up in the London suburbs and attended performing arts schools. She found critical and commercial success with the release of her first album, the jazzy "Frank," when she was just 20 years old. But even then her alleged drug use was becoming fodder for London tabloids.
Dr. Charles Sophy, an addiction specialist who works with celebrity clients, said that shining moments can often cause a relapse: "The trigger can be the emotional discomfort of things being happy ... it becomes that uncomfortable self-sabotoge where they don't know how to deal with something so wonderful and they get scared."
When Winehouse performed at the Grammys from London via satellite, taking a respite from rehab, some wondered whether that distraction was wise for someone battling a serious addiction. Now that she is attempting to resume performing, the question remains.
But Sophy said it could be a boost for Winehouse to do something that reaffirms a positive aspect of her life: "Anybody building on their strengths is the best thing to do."
In addition, Krim believes Winehouse's management and record label have her best interests in mind: "If they're going to have her perform on (the Mandela show), I think the people around her feel she's ready to do it."
She may be ready for Friday's performance, but doubts linger about when — or if — she'll be ready to resume her career. She had been working in the studio but reportedly stopped even before her recent hospitalization: Producer Mark Ronson, who won a Grammy for his work with the singer, recently said she wasn't "ready to record any music."
Meanwhile, her near-tragic personal life is keeping her in the headlines. If her troubles remain, the public may lose interest in that part of her life, too.
"This is very early in a career to have now to deal with all of this stuff," said Light, pointing out celebrities who have had monumental crashes — Michael Jackson, Whitney Houston and even Britney Spears — were in the public eye for years before their downturns.
"Once you've been a train wreck longer than you've been the pop star," he said, "I don't know how long people really care."