Fiona Apple

Fiona Apple remains one of the most artistically challenging and inventive recording artists to sell millions of albums in the 1990s and 2000s. Tidal, Apple's major label debut, came out when the singer-songwriter was only 18, yet she managed to sound old beyond her years, hooking in listeners all over the age spectrum and bypassing the teen pop ghetto that comes with a fiercely enforced "sell-by" date. Along with Apple's often harsh back story and moody, highly photogenic beauty, Tidal became a worldwide hit. Apple's follow-up was hindered by having an entire poem as its song title and a cover shot that downplayed her austere beauty. If that seemed like a deliberate attempt to make listeners concentrate on the music, it worked -- especially when When the Pawn... went on to win rave reviews. Once again, Apple's pained songcraft slightly obscured how good she really is. When Extraordinary Machine was finally released in 2005 it sailed to the Top 10 without the aid of any hit singles. Fans are patiently awaiting the follow-up.