2. Anna and Tess Coleman in Freaky Friday (2003)
She wears a plaid skirt, has a crush on a boy with a motorcycle, and she's in a rock band? We should have seen the warning signs. Lohan officially entered her rebellious teen years in Freaky Friday, and she played it with pitch perfect angst.
Fortunately, in the film, she switches bodies with her mother (Jamie Lee Curtis) so they can finally see eye-to-eye about what's bothering each of them. That is, how Lohan's character, Anna, isn't ready to accept her mom's new fiance three years after her father's death and how her mother doesn't understand her daughter's love of rock 'n' roll. Unfortunately, Lohan didn't get to switch bodies with her real life mom to make her realize how awkward it is when you see your own mom at the clubs you're going to. —TA