Top 5 Winona Ryder Films

1.) Heathers (1988)

F*ck me gently with a chainsaw..
Is this the most quotable film ever?! Basically a blueprint for Clueless and Mean Girls, it was a box office failure but now a cult classic. I've seen this a ridiculous amount of times.

2.) Girl, Interrupted (1999)

Reality is becoming too dense.
The female version of One Flew Over The Cuckoo's Nest? Ok, so Jolie may have slightly stolen Ryder's thunder by clinching the Academy Award, but this is still Winona's film. One of my favourites.

3.) Reality Bites (1994)

The ultimate Gen-X film. Weird that it was made by Ben Stiller of all people. A romantic comedy about the disenfranchisement of a group of 20-something friends/slackers and their career and lifestyle choices. A touchstone film for anyone fresh out of college and wondering what the hell to do with their lives. It's The Big Chill for the 90s.

4.) The Crucible (1996)

An allegory of the infamous McCarthy witch-hunts in 1950s America where directors and screenwriters were accused (and sent to prison!) of hiding subversive communist messages in their films, this film was even written by the playwright himself Arthur Miller. Not a box office success, but placing the themes of religious and political extremism at the forefront it ensures that it's more than just a period piece. Perfectly captures the paranoia and hysteria of the era.

5.) Night on Earth (1991)

A collection of five vignettes from Jim Jarmusch set in 5 different cities, it is a film about the temporary bond that a passenger forms with their taxi driver. Ensemble cast. Winona is the driver in L.A. escorting a Hollywood producer who ends up offering her a part in a movie, only for Ryder to turn it down because she wants to be a mechanic. A telling glimpse of the human condition and shot at night when people are vulnerable and more likely to speak what's on their mind.

Others that deserve a mention: The Age of Innocence (1993), Little Women (1994), Mermaids (1990), and Celebrity (1998) to name a few. I don't consider Black Swan "a Winona Ryder film". Neither is Night on Earth really but oh well..

Basically I was going to be damned if I picked a Tim Burton film in my top 5. I'm not a fan of Beetlejuice (1988) but Winona is awesome in it.