Ashlee Simpson might have started in the shadows of big sister Jessica Simpson, but that didn’t last for long. With her own reality television series on MTV, The Ashlee Simpson Show, that documented the process of making and coming out with an album – it was no wonder that her debut album Autobiography went triple-platinum. It was smooth sailing until Episode 568 of Saturday Night Live, where Ashlee was caught lip-syncing to a pre-recorded vocal track. After releasing two more albums, I Am Me and Bittersweet World, Ashlee announced she was marrying Fall Out Boy’s Pete Wentz. The good news didn’t stop there! The following month she announced they were expecting and in 2008 gave birth to their son, Bronx Mowgli Wentz. Since then, Ashlee filed for divorce in 2011 from her rocker husband.