Bobby (2006)

In her second ensemble indie of '06, Emilio Estevez's period drama following various people at the Ambassador Hotel the day of Robert F. Kennedy's assassination, Lohan (pictured with costar Sharon Stone) plays a young woman who marries her boyfriend (Elijah Wood) as a way to keep him out of Vietnam. Though reviews were mixed, the movie upped Lohan's profile as a dramatic actress and went on to score several Golden Globe nominations.