Hilary Swank
Just like many celebrities on this list, Swank also dropped out of high school to pursue acting. “I’m not proud to say I’m a high school dropout,” she told Today in 2010. After briefly attending South Pasadena High School in California, Swank made her film debut in the 1992 movie Buffy the Vampire Slayer. Just seven years later, she won her first Golden Globe and Oscar for her portrayal of Brandon Teena in Boys Don’t Cry.