The '90s It Girls You Wanted (and Still Kind of Want) to Be

Apple was only 18 when she dropped her debut single "Criminal" in 1996. The song's video grabbed headlines for its sexual undertones — which were then considered controversial, but now seem ridiculously tame — and the following year, Apple nabbed a Grammy and gave a scathing acceptance speech when she won an MTV VMA, telling the crowd, "This world is bullsh*t."