Winona Ryder: Top 5/Bottom 5 Movies

Appearing in Star Trek and a slew of summer movies, this former "it" girl has comeback potential.
Winona Ryder and Christian Slater in 'Heathers'
Winona Ryder and Christian Slater in 'Heathers' - New World Pictures
Joanne Hinkel

She was the "it" girl of the '90s, a Generation-X version of Audrey Hepburn with a pixie haircut, waif-like presence, and big brown eyes. Her natural, girlish style and too-smart-for-her-own-good attitude was a breath of fresh air into teen movies after the blond bimbo-laden roles of the '80s. Her name graced many a movie marquee between her breakout role in 1986's Lucas and 1999, the year she produced her first film, Girl, Interrupted. Yet it was having her name inked into the upper arm of fiancé Johnny Depp in 1990 that truly made her a household name.

In 2000, when she embarked on a two-year break from acting, Ryder became famous again, but not for the right reasons -- for a pill-induced shoplifting spree at Beverly Hills' Barney's. Ryder had poetically become a "Girl, Interrupted" -- another in a growing list of trainwreck-starlets who can't get insured on a movie set. But now, after flying under the radar, taking on sub-par roles in quirky indie movies over the past few years, 2009 just might be the year Ryder resurrects her career. She's in the hot new Star Trek prequel, as Spock's mother, and she has a supporting role in The Private Lives of Pippa Lee, Rebecca Miller's directorial debut, set to release in June.

In honor of Winona Ryder's Hollywood comeback, we present to you the best and worst of her career:

TOP 5

1. Heathers
She was "so very" as Veronica, the only popular girl not named Heather in her high school clique who actually hated being popular. Ryder nailed the sarcastic, irreverent, bored suburban teenager 'tude here in a surreal yet absolutely relatable way for any teen coming of age in the early '90s. Her chemistry with Christian Slater, her while-journaling monologues, and witty, rapid-fire one-liners ("Watch it Heather, you might be digesting food there.") hilariously spoofed high school ridiculousness like no other movie before it. This flick made her a movie star.

Mermaids2. Mermaids
Cher doesn't ride in the backseat very often, yet in the role of her disapproving teenager daughter in this '60s-era story, Ryder was the one to shine. After yet another failed relationship, free-spirited, eccentric, and unconventional Mrs. Flax (Cher) relocates with her two daughters Charlotte and Kate (Ryder and Christina Ricci) again, this time to Coney Island, Brooklyn, to start over. Ryder plays another rebellious teen, but this time she rebels against her mom's unconventional ways. She's desperate to fit in and have a normal ("proper") family life. She struggles with a decision to become a nun, but falls for the church bell ringer along the way. It's a sweet coming-of-age story.

3. The Crucible
The movie adaptation of Arthur Miller's play about the witchcraft craze in Salem, Massachusetts, did not receive stellar reviews, though Ryder's performance as the accusing young girl, Abigail Adams, did. Proving she could be a serious actress, Ryder delivered rage and righteousness in such a believable way that it seemed she really had become invaded by Satan, as she falsely claimed. Her performance here is more memorable than that of her co-star Daniel Day-Lewis. Imagine that.

Little Women 4. Little Women
Praised as the best movie adaptation of Louisa May Alcott's beloved early feminist novel, the lead role of Jo March was perfectly delivered by Ryder. Her ability to play a girl knowingly on the brink of womanhood was in full force. Even though period pieces would later prove to be a weakness for her, she did the bonnet, corset, and early American accent justice here.

Reality Bites 5. Reality Bites
With a Big Gulp from 7-11 firmly planted in her hand at all times and her group of college friends at her side, Winona Ryder's Lelaina Pierce rode the wave of jobless post-college existential crisis so realistically that it didn't bite at all to watch her -- it was a joy ride. This movie and her performance perfectly articulated Gen X's identity crises -- in a fun, celebratory way -- just as righteously as Singles portrayed Gen X's relationship crises.

BOTTOM 5

1. Dracula
Certain actresses are a perfect fit for period films: Keira Knightley, Gwyneth Paltrow, Kirsten Dunst. Winona Ryder -- not so much. She's too edgy, contemporary, and cool to pull it off convincingly. So, this adaptation of Bram Stroker's great novel just seemed silly at certain turns, particularly at the parts where Gary Oldman and Ryder had to conjure up desire. Those were blood-suckingly unconvincing scenes.

2. The House of Spirits
Isabel Allende's novel of the same name is a magical tour de force, a moving love story meets ghost story set in Chile, which could have been equally magical on screen (as was the similar Like Water for Chocolate). Alas, it was a flop. Critics at the time blamed the lack of Spanish-speaking actors -- except for Antonio Banderas, who adequately played Ryder's love interest -- in a story so entrenched in the poetic, magical realism of South American literature. Ryder seemed hopelessly out of place and unable to pull off the romantic passion the story required.

Autumn in New York3. Autumn in New York
The only enjoyable thing to watch in this movie was the striking fall foliage in Central Park. The chemistry between the fiftysomething Richard Gere and Ryder (unbelievably playing a dying 19-year-old) was nonexistent. This kind of melodramatic cheese is hard to pull off, and impossible when the romantic leads seem like a father and daughter.

4. Mr. Deeds
Ryder shines in dark, edgy, surrealistic comedies, like Heathers, Beetlejuice, and Edward Scissorhands. She's too eccentric for the obvious slapstick shtick of Adam Sandler. This movie, sadly, proved that the SNL funnyman's brand of humor was beginning to jump the shark anyway. And what was up with Ryder's hideously orange hair in this movie? Mr. Deeds did not get the job done for Ryder, or for critics, though it did bring home the bacon for the movie studio. It was Ryder's biggest box-office success yet, bringing in over $171 million. Ah, the irony.

Sex and Death 1015. Sex and Death 101
Unlike the others on this list, you've probably never heard of this movie. That's a good thing. Starring Simon Baker (TV's The Mentalist), this nearly straight-to-DVD release from '08 is about a bed-hopping businessman who refuses to settle down after he anonymously receives a list detailing all the women -- yup, 101 of them -- he will sleep with before he dies. Ryder plays the femme fatale who gets in the way of his conquering his list of conquests. Written and directed by Daniel Waters, who did Heathers, this sex comedy was supposed to be Ryder's comeback film instead of the B-movie lame attempt it turned out to be.

Let's hope that unlike her recent roles, Star Trek will beam Winona Ryder up the Rotten Tomatoes critics' charts once again.


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