50. Amy Winehouse, 'Back to Black'
It's sad to think back on how fresh this record sounded at the time – funny and hip, revivalist but forward-looking. Winehouse, a tatted 23-year-old with a beehive crown, matched the spirit of her R&B heroes, cussing, cracking wise and casually breaking your heart. She triggered a new era for brilliantly weird women in pop.