Amy Winehouse

Actual Age: 26 Perceived Age: 46

Besides looking like a crackhead, Amy Winehouse looks like an old crackhead. Like Lindsay Lohan, Winehouse's drug use has ravaged her skin and left her looking like Keith Richards. Winehouse was once a pretty woman, but her drug addiction, past eating disorders, and drug-related infections have taken a toll on her face. She's only 26 years old, but she looks 26 years old in dog years.