Winona Ryder’s Darkest Movie Is Streaming

Winona Ryder is the queen bee of strange and unusual teens everywhere, but this movie is unquestionably her darkest.

By Nathan Kamal | Published

Winona Ryder

In the 1990s, Winona Ryder was practically the patron saint of teens that considered themselves strange and unusual. She was cast in Tim Burton’s Beetlejuice as Lydia Deetz when she was only 15, a role that would have made her a goth icon all by itself. Over the course of the decade, she followed that up with a string of offbeat, dark films like Edward Scissorhands, Bram Stoker’s Dracula, Reality Bites, and Girl, Interrupted. All of these could have qualified as the darkest movie of many stars’ careers, but a movie that preceded all of these unquestionably takes the crown: 1989’s Heathers. The black comedy is one of the darkest and most chilling looks at peer pressure and high school in film history, and it currently streaming on Amazon Prime Video. 

Winona Ryder stars in Heathers as Veronica Sawyer, the only member of a clique of popular girls not named Heather. The queen bee is Heather Chandler (Kim Walker), constantly flanked by Heather McNamara (Lisanne Falk) and Heather Duke (a pre-Beverly Hills, 90210 Shannen Doherty). The quartet runs the school with an iron fist of humiliation and put-downs, but Winona Ryder longs for days with friends who were not as popular (or sadistic), like the constantly abused Martha “Dumptruck” Dunnstock (Carrie Lynn). The arrival of an odd, charismatic student named J.D. (Christian Slater, beginning his lifelong Jack Nicholson imitation) throws the layered, drama-driven ecosystem of Westerburg High School (reportedly named after the Replacements singer Paul Westerberg) off balance. Then things get really dark. 

Winona Ryder

Heathers is a movie that not only mercilessly satirizes and heightens the kind of class-informed peer pressure that could be found in any American high school, it finds a way to mine humor out of adolescent suicide, school bombings, sexual assault, depression, slut-shaming, and homophobia. Winona Ryder is initially a comparative innocent in the film, but that does not save her from being targeted by Heather Chandler for a minor slight and doomed to destruction. The movie also does not shy away from her attraction to Christian Slater, who is gradually revealed to be a serial killer in the making; she may not be as consumed with power and humiliation as Heather Chandler, but Winona Ryder is also not above attempting to low-grade poison her or assist in a double murder. Eventually, Heathers escalates things to an attempted mass murder discussed as an all-teen suicide and the utter destruction of the school. All in all, pretty dark. 

But that does not stop the movie from being consistently hilarious. Director Michael Lehmann and writer Daniel Waters (both in their filmmaking debuts) make the most out of moments like a grieving father crying out “I love my dead gay son” at a funeral, the serenely surreal opening sequence of three immaculately dressed, color-coded high school girls stomping on roses, and the bizarro, invented teenage slang of the movie. Winona Ryder had filmed the not-yet-released Beetlejuice but had to beg to play Veronica and got a department store makeover to convince Waters and Lehmann she could play an ordinary Midwestern teen. A pre-fame Brad Pitt unsuccessfully auditioned for the role of J.D., but it is difficult to imagine anyone but Christian Slater playing the role; the film walks the fine line of portraying him as seductive, rebellious, and finally unhinged. It also never fully gives details of why exactly he hates the world of high school so much, a daring choice for a movie making fun of high school stereotypes. 

While Winona Ryder would soon shoot to stardom, Heathers utterly flopped at the box office. It barely cracked a million dollars at the box office (far below its comparatively small $3 million budget), and critics largely did not know what to make of the viciously comedic subject matter. Like many movies with intensely dark stories, it would find a cult following on video release and was eventually lauded as one of the most prescient and brilliant comedies of its time. It also inspired an off-Broadway musical adaptation from Laurence O’Keefe and Kevin Murphy and a short-lived television series. Winona Ryder would go on to Academy Award nominations and a resurgent career with the Netflix hit Stranger Things, but Heathers will remain the defining movie of her cultural role as a strange and unusual youth.