Winona Ryder Is the Queen of Misfit Teenage Romance

Channeling goth ennui and doe-eyed sweetness, Winona shaped an entire generation's idea of unconventional love. We look back at her most iconic romantic roles that leave us clamoring "Wino Forever."

by Abbey Bender
Feb 14 2018, 4:48pm

An image from 'Heathers'. Cinemarque/New World

Few actresses have ever embodied the misfit teen girl in all her complex glory quite like Winona Ryder. Channeling goth ennui and doe-eyed sweetness in equal measure, Ryder left an indelible mark onscreen in the late 80s and early 90s, when she became a romantic lead and dream BFF to many a female viewer.

Heathers (1989), for all its pitch black humor and subversion of the teen movie genre, is anchored in Ryder’s considerable charm. Her character, Veronica, the outcast in the group of 80s alpha bitches named Heather, could easily play as one-dimensionally quirky and unrealistic, but Ryder has us empathize with this conflicted antiheroine. Kneeling over the coffin of Heather, dead after drinking poison, in a plan masterminded by Veronica’s bad seed new beau J.D. (Christian Slater), Veronica prays: "Technically, I did not kill Heather Chandler, but hey, who am I trying to kid, right? I just want my high school to be a nicer place. Amen. Did that sound bitchy?"

Ryder’s tone here is perfectly deadpan, but there’s something more poignant in there too: Who among us hasn’t wanted our high schools to be nicer, and what uncomfortable high school girl hasn’t idly dreamed of revenge? Ryder is a perversely aspirational figure here—half of an attractive, rebellious couple, stylish (she even rocks a monocle), and quick-witted—but she’s also down to earth in her feelings of frustration and angsty diary scribblings. "I don’t really like my friends," she sighs. The audience, in turn, thinks yes, but maybe she could like us.

Ryder’s characters in this era are inevitably girls in transition. In Mermaids (1990), Ryder, seeming younger and more awkward than she did in Heathers a year prior, plays the Catholicism-obsessed Jewish daughter of a single mother (played by none other than Cher), trying to negotiate her unsettled family life, with its constant moves, her religious beliefs, and her burgeoning crush on a young man in town. Ryder expresses a romantic problem that has plagued girls forever: "I do want to be good and virtuous," she says, "But it isn’t easy." Neither the girl next door type, a la Molly Ringwald, nor the bad girl, like Drew Barrymore, Ryder is perpetually hovering between the easy groups in which Hollywood so often wants to place young actresses. While an enduring crush (as exemplified by the amusing 2011 Onion headline, "Winona Ryder Finally Agrees to Sleep with Generation X") Ryder, in her roles as romantic leads, is rarely stereotyped.

Photo courtesy of Sunset Boulevard via Getty Images

Edward Scissorhands (1990), the movie in which Tim Burton wielded his stylized gothic whimsy most effectively, casts Ryder as Kim, the strawberry blonde (!) love interest of Johnny Depp’s misunderstood, not-quite-human title character. Kim, first seen in photographs, could easily be could just be a beautiful blank slate—but to the film’s credit, she has agency. Kim rejects her insensitive jock boyfriend and falls for Edward, and the back and forth close-ups between them feel straight out of a silent film (and are made more potent by Ryder’s real life relationship with Depp at the time.) Her character is also, crucially, the one telling the story: The film features a framing device of an old woman telling her granddaughter about Edward Scissorhands, and she ends up being none other than Kim, many years later. Kim’s perspective informs ours, and here, as in Heathers, Ryder is a popular teen who grows uncomfortable with the cruelty so often written into these social codes.

Edward Scissorhands gives Ryder several swoony romantic moments. Wearing a long white off-the-shoulder dress, Kim dances joyfully in the snow Edward makes with his ice sculptures. When she runs up to the mansion where he was created, the combination of the white dress, her fine features, and the dark, imposing house recalls the cover of a Gothic romance novel. It’s no surprise that just a few years later she’d bring her always-compelling performances to such lush, auteur-driven period pieces as Francis Ford Coppola’s Bram Stoker’s Dracula (1992) and Martin Scorsese’s The Age of Innocence (1993).

Ryder may be forever linked with Gen X, thanks largely to her role in Reality Bites (1994), but she can play a range of romantic protagonist roles convincingly. Her expressiveness, which comes through not just in her delivery but her large brown eyes and sly grin, isn’t explicitly stagey and over the top, but more subtle and sweet, fitting in a variety of eras and archetypes. Ryder seems approachable, but she can also be almost mythic. Consider the shots of her frolicking in snow and standing covered in soot and blood with a cigarette, in Edward Scissorhands and Heathers, respectively. These moments couldn’t be more aesthetically different: One is heartrendingly pure, the other dirty and cynical, and Ryder expertly sells them both as romantic teen iconography.