After toying around with her brother Alex's guitar, Winehouse received her first guitar when she was 13 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.Her boyfriend at the time, soul singer Tyler James, sent her demo tape to an A&R person. Winehouse signed to Simon Fuller's 19 Management in 2002. While being developed by the management company, she was kept as a recording industry secret. Her future A&R representative at Island/Universal, 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.
Beese introduced Winehouse to his boss, Nick Gatfield, and the Island head shared his enthusiasm in signing the young artist. Winehouse was signed to Island/Universal, as rival interest in Winehouse had started to build to include representatives of EMI and Virgin starting to make moves. Beese told HitQuarters that he felt the reason behind the excitement, over an artist who was an atypical pop star for the time, was due to a backlash against reality TV music shows, which included audiences starved for fresh, genuine young talent.
Winehouse's greatest love was 1960s girl groups. Her stylist, Alex Foden, borrowed her "instantly recognisable" beehive hairdo and she borrowed her Cleopatra makeup from The Ronettes.Her imitation was so successful, as the Village Voice reports: "Ronnie Spector-who, it could be argued, all but invented Winehouse's style in the first place when she took the stage at the Brooklyn Fox Theater with her fellow Ronettes more than 40 years ago-was so taken aback at a picture of Winehouse in the New York Post that she exclaimed, "I don't know her, I never met her, and when I saw that pic, I thought, 'That's me!' But then I found out, no, it's Amy! I didn't have on my glasses."
New York Times reporter, Guy Trebay, discussed the multiplicity of influences on Winehouse's style. Trebay noted: "her stylish husband, Blake Fielder-Civil, may have influenced her look." Additionally, Trebay observes:
She was a 5-foot-3 almanac of visual reference, most famously to Ronnie Spector of the Ronettes, but also to the white British soul singer Mari Wilson, less famous for her sound than her beehive; to the punk god Johnny Thunders...; to the fierce council-house chicks...; to the rat-combed biker molls photographed by the Swiss photographer Karlheinz Weinberger in the 1960s; to a lineage of bad girls, extending from Cleopatra to Louise Brooks's Lulu and including Salt-n-Pepa, to irresistible man traps that always seemed to come to the same unfortunate end.