Amy Winehouse

One of the most talked-about performers of the mid-2000s, Amy Winehouse is a powerhouse English R&B vocalist and songwriter whose troubles have threatened to upstage her impressive professional accomplishments. Winehouse, a rebellious girl (she'd been expelled from theater school at 14 in part for piercing her nose) from Enfield, London, began her professional career at 16 when her demo reached an A&R man. By age 20, she'd released her debut, Frank (2003), a jazz-tinged album produced by U.S. hip-hopper Salaam Remi that became a big chart hit in England and earned her several award nominations, including a nod for the Mercury Music Prize. Winehouse was later ambivalent about the album, and in the light of the fearless Back to Black it's easy to see why: Frank seems safe by comparison.

2006's Back to Black followed a period of personal upheaval for Winehouse: she'd had a terrible relationship. She also started wearing her hair in a beehive, got tattooed up and lost a noticeable amount of weight. The songs on Black were raw and cut deep, and the grooves did too: Remi returned for some songs, while the bulk were handled by Mark Ronson, a New Yorker/Londoner who'd become a go-to DJ on the hip-hop party circuit and who favored tracks that sounded like they'd been cut in the mid-Sixties. The trio made for excellent chemistry, and with Winehouse's strong songs Black became an instant hit in England, with the prescient "Rehab" going to Number Seven on the U.K. charts. The album was released in the U.S. in March 2007 and went to Number Six; "Rehab" made Number Nine on the American pop charts.

Unfortunately, a series of stumbling live appearances, barely disguised chemical abuse and a life dogged by tabloids pointed to an uncertain future for the singer. After an overseas marijuana bust and a series of struggles with her beloved husband, Blake Fielder-Civil (who was jailed for an unrelated obstruction of justice charge in the U.K.), Winehouse emerged on a London stage via satellite — she was unable to secure a traveling visa — to perform "Rehab" at the Grammy Awards on February 10th, 2008. She won five trophies that night, including Best New Artist and Record of the Year for "Rehab," and gave a special shout-out to "my Blake incarcerated" in her acceptance speech. After her triumphant Grammy night, Black climbed to Number Three. In May 2008, rumors surfaced that Winehouse had begun working on a new album with fellow troubled U.K. songwriter Pete Doherty.