Winona Ryder

She made her name playing smart, damaged young women in films that didn't quite fit any genre: Beetlejuice (1988), Heathers (1989), Edward Scissorhands (1990). Heathers was the sharpest of them, a black comedy about teenage social violence that still gets quoted decades later. She earned consecutive Oscar nominations, Best Supporting Actress for The Age of Innocence (1994) and Best Actress for Little Women (1995). That run established her as one of the most credible actresses of her generation, not just the weird girl who got lucky with Tim Burton.

The December 2001 arrest at Saks Fifth Avenue ($5,500 in merchandise, a conviction for grand theft) made her uninsurable and effectively ended her 90s run. She's described calling it a 'mutual break' with Hollywood. Fifteen years later, Stranger Things cast her as Joyce Byers, a frantic middle-American mom who believes her son is alive in another dimension, and a new generation discovered her. The final season dropped in 2025. Beetlejuice Beetlejuice (2024) brought her back to Tim Burton's universe. The comeback arc has a cleaner narrative than the career itself.

Her real name is Winona Horowitz. The surname 'Ryder' came from a Mitch Ryder & the Detroit Wheels record that was playing when someone called to ask how she wanted to be credited. It's more accidental than it sounds. She was cast as Mary Corleone in The Godfather Part III but dropped out, a slot that went to Sofia Coppola. She spent nearly a decade pushing to get Girl, Interrupted made. There's a running story that she and Keanu Reeves may be legally married because Francis Ford Coppola used a real Romanian priest for their wedding scene in Bram Stoker's Dracula (1992). She raised it herself in a 2018 interview. Nobody's filed for annulment.