Georgia Rule (2007)
This the May 2007 release of forgettable Garry Marshall's forgettable dramedy preceded Lindsay's first DUI and the beginning of the end of her squeaky clean image. In it, she portrays Rachel, a teenage wild child in need of strong parental guidance, forcing her mother (Felicity Huffman) to whisk her off to Idaho to stay with her commanding grandmother (Jane Fonda). The inciting incident for Rachel's exile? A car crash. Garry Marshall (also responsible for the likes of Valentine's Day and New Year's Eve) has been called many things, but allow us to be the first to label him as fantastically ahead of his time. Killer casting instincts on this one dude.