That opportunity led to her recording contract with Island Records. By the end of 2003, when she was 20 years old, Island had released her debut album, Frank. With contributions from hip-hop producer/keyboardist Salaam Remi, Winehouse's amalgam of jazz, pop, soul, and hip-hop received rave reviews. The album was nominated for the 2004 Mercury Music Prize as well as two Brit awards, and its lead single, "Stronger Than Me," won an Ivor Novello Award for Best Contemporary Song.

Following Winehouse's debut, the accolades and inquiring interviews appeared concurrently in the press with her tempestuous public life. Several times she showed up to her club or TV performances too drunk to sing a whole set. In 2006, her management company finally suggested that she enter rehab for alcohol abuse, but instead, she dumped the company and transcribed the ordeal into the U.K. Top Ten hit "Rehab," the lead single for her second, critically acclaimed album, Back to Black. Containing evocative productions from Salaam Remi and British DJ/multi-instrumentalist Mark Ronson, the album somewhat abandoned jazz, delving into the sounds of '50s/'60s-era girl group harmonies, rock & roll, and soul. The fanfare over the release was so great that it started to spill over onto U.S. shores; several rappers and DJs made their own remixes of various songs -- not to mention covers by Prince and the Arctic Monkeys.

One month after Winehouse won Best Female Artist at the Brit Awards in February 2007, Universal released Back to Black in the U.S. The LP charted higher than any other American debut by a British female recording artist before it, and it remained in the Top Ten for several months, selling a million copies by the end of that summer. Just as in the U.K., she became the talk of the town, landing on the covers of Rolling Stone and Spin magazines. Not long afterward, though, Winehouse canceled her North American tour. Early reports revealed that she was entering rehab for alcohol and drug addiction, but her new management denied the claims, stating it was due to severe exhaustion. Her erratic behavior kept her and her new husband, Blake Fielder-Civil, constantly in the tabloids and on and off stages on both sides of the Atlantic, but in late 2007 American fans were finally given a chance to hear Winehouse's early work, with a slightly abbreviated (two songs removed and one added) version of Frank.

Winehouse died on 23 July 2011 in unexplained circumstances.