Marketing can be a funny thing in the music business. Look at Garth Brooks, who tried a dozen different gimmicks before becoming the world's most famous country singer. Even the Beatles were shaped and forged into the lads we know after an early career dressing like hooligans and nailing condoms to walls during performances.
Image is just too big a part of the game to ignore. So it's probably not surprising that many of the female artists we know and love did not step out of a clamshell, fully realized, into the forms we are most familiar with.
Probably the most famous example on this list, the woman that defined the '90s with her deep lyrics and daring music started out much more Debbie Gibson-ized with a full backing band that included, no joke, Guns N' Roses' Matt Sorum. The whole thing was a ridiculous plan by Atlantic records and thankfully died an early death, which allowed her to try again with the album Little Earthquakes.