There is no one before or since Winona Ryder who has captured the essence of what it means to be effortlessly striking. Sure, gamine actresses abound, but no one has the rough-hewn edge of Winona. Her debut film was the bittersweet Lucas in 1986, followed by the critically acclaimed–though marginal–Square Dance in ’87. It wasn’t until Tim Burton’s Beetlejuice that Winona’s place in the chronicles of film history was solidified.
Her “it” quality seemed only to amplify as the 90s progressed, reaching an intense pinnacle with Edward Scissorhands. Ryder’s relationship with Johnny Depp also helped her elevation into A-list status (though Depp was only at the beginning of his rise to go-to leading man). Regardless of her campy film choices, which were firmly established by Heathers and Great Balls of Fire! before Edward Scissorhands, Ryder has always somehow managed to stay mainstream, whereas others–including Christina Ricci, who comparisons are often drawn to–have never quite been able to attain Ryder’s level of fame.
Moreover, Ryder’s pull was clearly strong enough to prompt Depp to tattoo “Winona Forever” on his shoulder in 1990 when the two were still engaged. Ultimately, Depp had the ink altered to read the much more alcoholic motif, “Wino Forever.” After her split from Depp, Ryder’s career seemed to take a brief downturn with The House of the Spirits and How to Make an American Quilt, with the iconic, voice of a generation Reality Bites thrown in to offset the badness. Nonetheless, Ryder sustained audience interest, making her triumphant return to glory in 1999 well worth the wait. With Girl, Interrupted, Ryder may have been outshined by Angelina Jolie, but the general goodness/realness of the film revealed Ryder at one of her peaks.
Unfortunately, this was followed by the terribleness of Autumn in New York with Richard Gere. Things didn’t get much better for Ryder on a personal level either when, in 2001, she was arrested for shoplifting at Saks Fifth Avenue (prompting many to bring up her ironic line from Girl, Interrupted in which she states, “Have you ever stolen something when you had the cash?”). At the time her only upcoming release to speak of was Mr. Deeds–another beacon of dreadfulness during this period of her life.
Objectively, Ryder didn’t manage to land a decent film role again until 2010’s Black Swan, quickly having transitioned into that age in Hollywood where you’re expected to play an aging hag or nothing at all. Even though Ryder has had her fair share of lows, it is still safe to say that there will never be another adequate imitator. And, if we’re lucky, the upcoming release of Beetlejuice 2 will vindicate her once again.