Fiona Apple "Criminal"

The worst part about this song is its quality was overshadowed by the controversy that surrounded its video, which has become one of the most iconic of the '90s, has been imitated numerous times, and seems tame compared to some videos in recent years.

The mid-'90s had a slew of bad-girl songs that pushed the boundary of what women could sing about and get those songs played on commercial radio. Two years before "Criminal" was released, Alanis Morissette's "You Oughta Know" gave a heavily-redacted account of acts she performed (and wished to perform) on an ex-lover.

In that vein, Apple confessed (with few details) that she was also quite naughty, cheating on her boyfriend.

Confessional songs, which were nothing new by any means, soon had a bit of a moment on MTV and radio as artists spilled their souls on topics like love, money, and the environment.

However, few artists could hope to combine the raw emotion and raspy vocal technique Apple gives in her pleas for forgiveness and repentance.

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