#16: John Cusack Now
Cusack quickly broke out as a leading man in classics like Say Anything…, High Fidelity, and Grosse Pointe Blank, becoming one of the most beloved actors of the 1990s. Known for his offbeat charm and quick intelligence, he’s built a long, varied career in both romantic comedies and thrillers.
In recent years, he’s focused on indie films and writing, staying selective about roles while maintaining a loyal fan base. Cusack remains a respected, thoughtful figure in Hollywood, far removed from his trench-coated geek days in Sixteen Candles.