2. Ashlee Simpson Is Nearly Unrecognizable! See Her Then and Now
Ashlee Simpson stepped out of sister Jessica’s shadow with pop hits like “Pieces of Me” and “Boyfriend” and an MTV reality show of her own. But then she made a series of questionable decisions: lip-syncing on SNL; starring in (and being written off of) Melrose Place; marrying rocker Pete Wentz; and naming her son after a borough and a Jungle Book character (Bronx Mowgli).
Wonder what the multi-talented pop singer looks like now? Click here for the full gallery.