British diva Amy Winehouse scored legions of fans with her 2006 album, Back to Black, which showed off her brassy, sweet-and-sour voice and taste for meticulously retro soul music.

But Winehouse soon made headlines for the wrong reasons. Suddenly, “Rehab,” a booming hit single about how she refused her handlers’ requests to get sober, didn’t seem so funny.

The London-born singer had a rebellious steak from an early age. Expelled from theater school at age 14 for piercing her nose, Winehouse began her career two years later when her demo reached an A&R man. She was signed to Island/Universal Records, and by the time she was 20, she’d released her 2003 debut, Frank. The jazz-tinged LP — helmed by U.S. hip-hop producer Salaam Remi — became a commercial and critical hit in England, earning Winehouse a nod for the prestigious Mercury Music prize.

Winehouse recorded Back to Black following a period of what seemed like personal upheaval: After ending a relationship, she lost an alarming amount of weight, got multiple tattoos, and started wearing her hair in a beehive. Winehouse channeled her dark feelings into her music, writing raw, emotional songs that Remi and up-and-coming London/New York producer Mark Ronson boosted with funky instrumentation and soulful Motown grooves. (One track, “Tears Dry On Their Own,” uses a Marvin Gaye/Tammi Terrell sample.) The trio had hit on a winning formula, and Black became an instant hit in England, with lead single “Rehab” shooting to Number Seven on the U.K. charts. When the album was released in the U.S. in March 2007, it hit Number Six on the pop charts (it peaked at Number Three a year later). Black’s reach was huge: it was the best-selling album of 2007, and it scored five awards at the 2008 Grammys, including Song of the Year, Record of the Year and Best New Artist.

But as her fame grew, Winehouse — who married sometime-boyfriend Blake Fielder-Civil in May 2007 — was dogged by a series of stumbling live appearances and barely disguised drug and alcohol problems. Tabloids chronicled everything from an overseas marijuana bust in 2007 to a series of violent public fights with her husband (who was jailed in 2008 for an unrelated obstruction of justice charge in the U.K.). After several well-publicized benders — plus a 2009 arrest for assault and hospitalization for a reported overdose — Winehouse went to St. Lucia in early 2009 to work on new music with Back to Black partner Remi.