10 Actresses Whose Careers Went Downhill After Winning An Oscar

4. Hilary Swank

Oscar Wins: Best Actress, Boys Don't Cry (2000)/Best Actress, Million Dollar Baby (2005) It may be odd to see a two-time Oscar winner on this list, but Hilary Swank has had an odd career. When she won her first Oscar, her career was on the rise, as expected. She starred in critically-acclaimed movies such as Insomnia and 11:14, and then took audiences by storm with her powerful performance in Clint Eastwood's Million Dollar Baby. At age 30, with two Oscars, it seemed Swank could not do anything wrong. But the films she's appeared in since Million Dollar Baby have mostly been stinkers. If they weren't complete bombs (such as The Black Dahlia, The Reaping, Amelia), then they were general disappointments. While her movie choices may not seem as egregiously bad as other actresses on this list, seeing a two-time Oscar winner star in mediocre movies for almost a decade just seems wrong, doesn't it? She does not have many upcoming films on her slate, but let's hope she still has more great performances up her sleeve.