Just before her disastrous European tour last month, the infamously addicted singer entered a rehabilitation centre on doctor's orders, ostensibly to ensure that she would be ready to perform. She left a week later, with her publicist announcing she was "raring to go."
She clearly wasn't. At the concert's kickoff June 18 in Belgrade, Serbia, Winehouse struggled to remember the words to her songs, stumbled around the stage and even tried to get one of her background singers to warble for her.
Her tour was soon cancelled. A little over a month later, she was dead.
There's a long history, to be sure, of performers who wither away due to addiction while the world watches, but Winehouse's death on Saturday at age 27 has rekindled questions about the role the music industry should play in helping stars kick self-destructive habits.
Why, for example, was Winehouse still being booked for concerts even though she was battling a devastating addiction? Could the entertainment community have done more to save one of its most gifted young artists?
Natalie Cole thinks so.
A former heroin addict herself, Cole was critical of the industry after Winehouse won five Grammys in 2008, including record and song of the year for "Rehab," the song in which Winehouse rebuffed help for addiction.
Winehouse performed triumphantly during the Grammy telecast that year - but did so via satellite from London, in part because she couldn't get a visa to go to the United States, and also because she was in rehab at the time.
Her treatment facility gave her a brief reprieve so she could perform for a worldwide audience and receive her accolades.
Cole said the entire episode sent a bad message. "Her life was at stake. I mean, she was trying to get off heroin, which is probably one of the most difficult drugs to recover from," Cole said.
"I just don't get it. What more can we do other than everybody needs to grow up? Hollywood needs to grow up and stop glorifying this kind of behavior and thinking it's cute," she said.
Cole said Winehouse shouldn't have been trying to perform, given her condition. Winehouse had been in and out of rehab and battled a host of problems since her Grammy triumph, had not released another album and was performing only sporadically.
Pax Prentiss, founder of the Malibu, California.-based Passages treatment centre, said it's often in an addicted performer's best interest to be working, rather than living an unstructured lifestyle without getting help.
"It keeps them busy. ... I don't think it's good to have idle time," said Prentiss, a former addict himself. "But in saying that, Amy was not ready to go back to work. ... She clearly was not ready for the stage, or for life in general."
Winehouse's management and record label did not respond to requests seeking comment for this story.
Prentiss said Winehouse's problem may have been that the underlying causes leading her to take drugs were not dealt with. But he added that he didn't think the music industry "should try and manage Amy's personal life."
Cole disagreed. She said the industry has a responsibility to step in and push an artist out of the spotlight until they get their personal act together.
"Somebody in that circle needs to be there to go, 'Uh uh, you're going to have to sit down and get some help,'" she said. She said she has seen past examples of a record label halting production of new albums until an artist gets clean.
"There's too many yes people around these artists. They're very easily influenced, they're very vulnerable," she said.
Neil Portnow, CEO and president of the Recording Academy, which puts on the Grammys, agreed that musicians who are battling drugs are sometimes given guidance from people who may not have their best interests at heart. But other times, he said, it's not that simple.
"Sometimes, that becomes a challenging decision to make," he said. "Do you say to an artist, 'Come off the road, don't make records, don't do endorsements, don't do anything on a business level because you have to deal with your health'?
"But at the same time, that will immediately cut off all income, not only to the artist but also to their representatives?"
Portnow added that those close to an artist sometimes don't know how to handle the situation, that sometimes it takes the artist to want to get better and do the work to achieve that. Yet the addiction may not let that happen, he said.
Clearly, Winehouse did try; despite her famous song, she attempted rehab several times.
Describing her own battle against addiction, Cole said she was at her worst when she was still performing. She said people in her camp "would be sitting back there with their fingers crossed, praying that I would get through a show.
"I even had a few people who no longer wanted to work with me, because they just didn't want to see me self-destruct," she said.
The Recording Academy's MusiCares assistance programme is designed in part to help musicians battling such addictions, providing anonymous financial and other support. Portnow said there are also guides to help the people around an artist deal with such situations.
"The most basic premise is the welfare and well-being of a musical artist, or any artist, or any human for that matter, is paramount," he said.
Portnow said the academy thought Winehouse was getting the help she needed when they had her perform during the Grammys.
"Our understanding at the time was that she was cleared medically to perform," he said. "It was a performance of a lifetime for her, and it certainly appeared that she was in fine form to do that."
Cole said she wished Winehouse would have skipped the Grammys and other events and concentrated on getting clean. After years of abuse, Cole said, it took three members of her own business team to take her aside and threaten to quit working with her until she got help.
She remains grateful for that ultimatum.
"They cared. And that's all we have to do. We have to care," she said. "Somebody needed to care about that girl, and I don't know if she had that."
