Girl, Interrupted – Angelina Jolie bests Winona Ryder

Girl, Interrupted (1999) has stood out in critics' eyes since the 2000s. Known for the role that shot her to stardom, Angelina Jolie outshined Winona Ryder, her co-star and lead in the film, who was arguably one of the most famous actresses at the time. The New York Times wrote of Jolie, saying her "ferocious, white-hot performance captures the scary allure of this daredevil and brutal truth teller, the movie's answer to R.P. McMurphy of Cuckoo's Nest." Jolie went on to win the Academy Award for Best Supporting Actress for her role in the film.