After toying around with her brother Alex's guitar, Winehouse bought her own when she was 14 and began writing music a year later. Soon after, she began working for a living, including, at one time, as an entertainment journalist for the World Entertainment News Network, in addition to singing with local group the Bolsha Band. In July 2000, she became the featured female vocalist with the National Youth Jazz Orchestra; her influences were to include Sarah Vaughan and Dinah Washington, the latter of whom she was already listening to at home. Amy's best friend, soul singer Tyler James, sent her demo tape to an A&R person. Winehouse signed to Simon Fuller's 19 Management in 2002 and was paid £250 a week against future earnings. While being developed by the management company, she was kept as a recording industry secret although she was a regular jazz standards singer at the Cobden Club. Her future A&R representative at Island, Darcus Beese, heard of her by accident when the manager of The Lewinson Brothers showed him some productions of his clients, which featured Winehouse as key vocalist. When he asked who the singer was, the manager told him he was not allowed to say. Having decided that he wanted to sign her, it took several months of asking around for Beese to eventually discover who the singer was. However, Winehouse had already recorded a number of songs and signed a publishing deal with EMI by this time. Incidentally, she formed a working relationship with producer Salaam Remi through these record publishers.
Winehouse won three Ivor Novello Awards : in 2004, Best Contemporary Song for " Stronger Than Me "; in 2007, Best Contemporary Song again, this time for " Rehab "; and in 2008, Best Song Musically and Lyrically for " Love Is a Losing Game ." She also won the 2007 Brit Award for Best British Female Artist, having been nominated for Best British Album, with Back to Black .