7. Girl Interrupted (1999)
As a sociopath named Lisa, Jolie made a difficult part look easy to play in this story of mental afflictions and treatment alongside co-stars Winona Ryder, Brittany Murphy, Vanessa Redgrave, and Whoopi Goldberg. She truly showed her versatility in this performance, winning the 1999 Oscar for Best Supporting Actress and standing out among the rest.
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