Amy Winehouse (2007)
Winehouse was made for the BNA award, and it was made for her. So young. So female. So singer-songwriter-y. Kinda like Taylor Swift, who was also nominated that year. Except the Grammy voters figured Winehouse was the more promising rookie, since she was the one with the tattoos, the English accent and the boyfriend in jail. ("For my Blake incarcerated!") Despite her outlaw rock cred, Winehouse was already essentially retired by the time she won. She lived another three and a half years, but released no new music in this time, while Swift kept writing truckloads of great songs. By the time of Winehouse’s tragic death in 2011, Swift had already made another two blockbuster albums, Fearless and Speak Now.