Winona Ryder, 49 – Actress

In the ’90s, a young Winona Ryder helped redefine what ‘cool’ looked like, after becoming a favorite actress of high-pedigree directors such as Tim Burton and Martin Scorsese. Today, it’s hard to believe Ryder is 49 years old already! Not only because time flies, but also because she looks much younger than that. But in addition to staying beautiful, Ryder has managed to keep busy. She’s recently made it to the Netflix hit series Stranger Things, and she’s delivered a convincing performance in the must-watch HBO miniseries The Plot Against America.