While she had been a staple of the British music scene since releasing her debut album, Frank, in 2003, it was her 2006 album that launched her as an international star and ushered in a new sound that harked back to the girl-group days of the '50s and '60s, leading to a number of copy-cat artists releasing albums around the same time.
On her 2006 track "Rehab," Winehouse chronicled her love of partying hard and her defiance to seek help for it, setting a course for the issues in her personal life. Midyear, Winehouse's camp began denying the singer had a substance-abuse problem, as she began to cancel dates, a string of events that would become commonplace in her short-lived career.
Even as the issues in her personal life began to cause speculation, her music career was thriving, with accolades flowing in from rappers like Jay-Z, who began appearing on remixes of her songs, broadening her appeal to a wider spectrum of audiences beyond retro-leaning hipsters.
But her legal troubles would make just as many headlines as her award wins and chart-topping success. In October 2007, she was arrested for marijuana possession, with her equally troubled husband, Blake Fielder-Civil, by her side in Norway.
As professional accolades flowed in, evidence of her drug problems became more and more evident. In January 2008, a video surfaced allegedly showing the singer smoking crack. Weeks later, she would check into rehab.
In February, she wasn't be able to attend the Grammys after her Visa was denied, however she did appear via satellite. At the show, she took home five trophies, including the big prize, Record of the Year.
As 2008 rolled along, authorities continually questioned the singer in a number of cases, including an assault case in April and a drug-related arrest in May tied to the video of her allegedly doing drugs. Those charges were later dropped.
In June of that year, she went public with the news that she had an early stage of emphysema, as confirmed by her father, who became her mouthpiece and her biggest supporter in the face of her personal adversities. Later in the year, she hit the stage again in shows that were both redeeming and disastrous.
Things did not slow down for Winehouse in 2009. Her husband filed for divorce in January of that year, and in March, she had to cancel her Coachella set after being charged with assault in connection with a 2008 incident.
Regardless of her legal and health issues, she kept booking gigs, though not necessarily to successful results. She walked out early on a gig in St. Lucia in May.
However, by December, she was once again charged with assault in connection with another incident at a theater in the U.K. where she heckled a performance of "Cinderella" and reportedly assaulted theater manager Richard Pound, who complained that Winehouse had pulled his hair, punched him and kicked him when he asked her to move seats.
After laying low for a good part of 2010, Winehouse appeared at a gig for her producer Mark Ronson in London, where she messed up the lyrics to their track "Valerie" and was seen drinking and being boisterous offstage. Despite the antics, she promised new music by early 2011, a promise she did not keep.
Her last stint in rehab was reportedly in May 2011, however, her attempts to get clean never truly helped her defeat her demons. At a disastrous show in Belgrade in June, she showed up more than an hour late, then repeatedly left the stage mid-performance, forgot lyrics to her songs and even dropped a microphone. Shortly after, the singer canceled more tour dates.
On Saturday, Winehouse was found dead at age 27, just five weeks after her last show, leaving behind a legacy of fame for both her musical influence and her troubles.