Winona Ryder movies: 15 greatest films, ranked worst to best, include ‘Heathers,’ ‘Little Women,’ ‘Beetlejuice’

Winona Ryder has had her career ups and downs since she made her film debut at age 15 as a high-schooler who befriends Corey Haim, her bully-targeted classmate, in 1986’s “Lucas.”  She reigned as one of the most in-demand film actresses in the ‘90s as she transitioned into more adult roles. Ryder hit an unfortunate speed bump in 2001, after she faced shoplifting charges for stealing $5,500 worth of merchandise from a Saks Fifth Avenue department store. She ended up sentenced to three years of probation, 480 hours of community service and various fines while receiving both psychological and drug counseling.

Ryder took time off from acting between the time of her arrest until 2005, when she appeared in a string of indie films. But her true comeback arrived in J.J. Abrams‘ 2009 “Star Trek”  reboot as Spock’s human mother Amanda Grayson. These days, she is best known as single mother Joyce Byers, whose 12-year-old son mysteriously vanishes on Netflix’s nostalgia-driven sci-fi-horror series “Stranger Things.” A third season of the show will arrive next year.

In honor of her 47th birthday on October 29, 2018, here is a salute to Ryder’s 15 greatest films, ranging from worst to best. Tour our photo gallery above featuring “Heathers,” “Little Women”  and “Beetlejuice” to see if your other favorites made the cut.

In the fourth movie in the original “Alien” franchise, Ryder is Annalee Call, an android mechanic who is tasked to assassinate Ellen Ripley’s clone (Sigourney Weaver), who carries an alien queen embryo inside of her. There is a reason why Ryder never played an action-hero type again and the messy evidence splattered here is all over the place in this unnecessary sequel. The Washington Post review suggests she was used as bait to attract a younger generation of “Alien” fans – ones who never quite materialized.

Dennis Quaid’s manic dedication to playing rock and roll legend Jerry Lee Lewis is the best reason to watch this rather embroidered, almost cartoony biopic. Ryder has the uneasy task of playing The Killer’s 13-year-old child bride, Myra Gale Brown – who, besides being under-age, just happens to be his second cousin. Despite the unsavoriness of the scandalous relationship, the actress exudes an effective-enough innocence though never quite suggests what she really thought of the wild man she wed.

13. MERMAIDS (1990)
This story set in 1963 focuses on a footloose, nomadic mother (Cher) of  two — Kate, a grade-schooler (Christina Ricci in her film debut), and Charlotte, a teen (Ryder) — whose penchant for ill-fated affairs have forced  her family to move 18 times. Ryder’s character is embarrassed by her mom’s lifestyle and is drawn to Catholic nuns (despite being Jewish) while her sister is a swimming fanatic who likes to hold her breath underwater. But most critics at the time suggested that Ryder’s sweet naivety and humorous teen angst when Charlotte becomes hormonally drawn to a handyman at a nearby convent is the only thing keeping this coming-of-age comedy afloat besides Cher’s rendition of the “Shoop Shoop Song.”

This drama based on a 1993 autobiography about author Susanna Kaysen’s time in a psychiatric hospital in the ‘60s was executive-produced by Ryder herself as a way to re-instate her standing as a lead actress. While she had the headlining role as a sufferer of borderline personality disorder, her performance was over-shadowed by newcomer Angelina Jolie’s over-the-top performance as a charismatic rebel of a sociopath who has escaped the institution multiple times but is always eventually caught and taken back. The film became Jolie’s calling card instead, especially after she won a supporting actress Oscar.

Ryder is Finn, a student at Berkeley, who spends her last summer before getting married with her grandmother (Ellen Burstyn) and great aunt (Anne Bancroft) at their rambling California home. They and their women friends are into making quilts – and their latest project is to celebrate Finn’s wedding. The bride-to-be isn’t fully sure about tying the knot and escapes into the life stories of the women that inspire their piece of her quilt-to-be.   She meets a handsome young man at the local pool (Johnathan Schaech) and they have a brief fling, which eventually helps her make up her mind. The film got mixed reviews – The Los Angeles Times declared it “patchy” — despite the impressiveness of its female ensemble cast.

Gary Oldman is a hoot as the titular blood-sucker and Anthony Hopkins is no less over-the-top as the vampire hunter Van Helsing. But Ryder as Mina Murray, the fiancée of Dracula’s lawyer Jonathan Harker (Keanu Reeves, not quite up to the task at hand, including his odd British accent), and reincarnation of the count’s lost love, had problems acting opposite Oldman, who was supposed to charm her character. Critics had concerns about the uneven plotting, but praised Oldman’s romantic take on the seductive immortal being as well as the use of physical effects over computerized trickery. The film won Oscars for costume design, sound editing and makeup.

Ben Stiller’s now-cult ode to Gen-X aspirations and disappointments allowed Ryder with the rare opportunity to do a contemporary film – or, as she put it, “I really wanted to wear blue jeans for a change.” It was her choice to recruit Ethan Hawke as coffee-house guitarist Troy, who competes with Stiller’s Michael, a cable channel exec,  for  the affections of her wannabe filmmaker, Lelaina. Meanwhile, her best friend Vickie (Janeane Garofalo), a sales person at a Gap store, fears her sexual habits might have exposed her to AIDS. Favorite scene: When Lelaina and Vickie along with Zahn’s Sammy spontaneously start dancing to The Knack’s 1979 hit “My Sharona” while buying snacks at a gas station’s food mart.

8. STAR TREK (2009)
Ryder’s cameo as Spock’s human mother, Amanda Grayson, in Abrams’ reboot of the “Star Trek” movie franchise went a long way to re-establish her cred again in pop culture. CNN declared her to be “quietly effective” while Salon described her performance as “nicely wrought” in a small role as her status as an Earthling causes her young half-Vulcan son to be a bully target. It also was a rare case of her being associated with a highly anticipated and box-office-busting summer hit.

7. BLACK SWAN (2010)
This psychological thriller about the cost of artistic perfection provided Ryder with a small yet plum role as Beth McIntyre, an over-the-hill prima ballerina who is forced into retirement from a New York company after Natalie Portman’s Nina Sayers takes her place as the innocent White Swan and seductive Black Swan in a performance of “Swan Lake.” An inebriated Beth accuses her of sleeping with Thomas, the artistic director (Vincent Cassel), to get the role. The next day, Nina discovers Beth was hit by a car while walking in the street – and Thomas believes she is at fault. Again, Ryder wisely associated herself with a film that not only did well at the box office – taking in $329.4 million worldwide – but also claimed five Oscar nominations, including Best Picture and Best Director. Its lone win went to Portman as lead actress.

6. THE CRUCIBLE (1996)
In Salem, Massachusetts in 1692, several girls in the Puritan community encounter a Barbadian slave named Tituba. One of them, Abigail (Ryder), kills a rooster and drinks its blood, while wishing that Elizabeth (Joan Allen), the wife of John Proctor (Daniel Day-Lewis), dies. Her uncle, a reverend, comes upon them and his daughter, Betty, passes out while another girl becomes unconscious. It is learned that Abigail had an affair with Proctor and a trial is held that pits him against the girls. The film, well-reviewed though a notorious flop, was Oscar-nominated for Allen’s supporting role and Miller’s adapted screenplay.  Ryder received praise for her “erotic rage” by Time magazine and Rolling Stone proclaimed that she “offers a transfixing portrait of warped innocence.”

In late-19th century New York, lawyer Newland Archer (Day-Lewis) is betrothed to the young May Welland (Ryder). Her cousin, an American heiress (Michelle Pfeiffer), returns to the city after leaving her Polish count husband and with her reputation now in tatters. May’s family supports her while Archer becomes drawn to the worldly Countess. He becomes torn between his intended and her cousin.  He and May wed, but the Countess returns  to the city before suddenly departing again after May tells her she is pregnant – suggesting she is not as out of the loop as she seems. Rolling Stone declared that “Ryder, at her loveliest, finds the guile in girlish May – she’ll use any ruse that will help her hold on to Archer.” The film won an Oscar for its costume design along with nods for supporting actress for Ryder, adapted screenplay, score and art direction.

An old inventor (Vincent Price) creates an artificial human being and tutors him like a son inside his crumbling Gothic mansion. The man dies before he can attach real hands to invention, leaving him with scissors instead. A door-to-door saleswoman named Peg Boggs (Dianne Wiest) happens upon Edward and invites him to her home, where he is welcomed by most of the neighbors. He repays their kindness by using razor-sharp limbs to shape bushes into topiaries, groom pets and style the hair of the women. Peg’s daughter, Kim (Ryder), is attracted to Edward but her jealous boyfriend resents the misfit intruder. Ryder and Johnny Depp were a real item at the time and their youthful chemistry brings a special glow to this modern-day fairy tale. When Kim says, “Hold me,” Edward can only reply, “I can’t.”  The film was Oscar-nominated for makeup but lost to “Dick Tracy.”

3. HEATHERS (1989)
At 17, Veronica Sawyer (Ryder) feels lucky to be part of a high-school clique with three rich and attractive cool girls with a penchant for jackets with boxy shoulders who are all named Heather. Their very presence causes the other students to cower and avert their eyes. She becomes distracted by a new student named Jason “J.D.” Dean (Christian Slater, in young Jack Nicholson mode) whose rule-breaking ways and sophisticated tastes impress her. After the top Heather threatens to ruin Veronica’s reputation, J.D. gives her drain cleaner to drink and kills her. They cover up the crime by forging a suicide note. More macabre murders passed off as suicides take place under the direction of J.D.  This wickedly sick twist on typical teen shenanigans has gained a rabid cult following, abetted by Ryder’s approachable character. The New York Times described her as being “both stunning and sympathetic as the watchful Veronica” while declaring her as “a promising new star.” They weren’t wrong.

This horror comedy is about a married couple, the Maitlands (Geena Davis and Alec Baldwin), who die in a crash and are forced to haunt their beloved former home now occupied by a pretentious yuppies in the form of an ex-real estate developer (Jeffrey Jones) and his wife (Catherine O’Hara). Their goth-girl teen daughter, Lydia (Ryder), is able to interact with the Maitlands because of her empathetic nature and decides to summon crude, rude and otherworldly ghoul Betelgeuse (Michael Keaton), a kind of burlesque clown from hell, to help scare her parents away, even if he demands to wed Lydia as payment. Burton hired Ryder after seeing her in “Lucas” and she provides the black-clad moody anchor that keeps this eye-popping fantasy from spinning out of control. “Beetlejuice” won an Academy Award for Best Makeup.

1. LITTLE WOMEN (1994)
And you thought there were too many versions of “A Star Is Born.” This fifth big-screen adaptation (a sixth came out in 2018 and a seventh is due next year)  of Louisa May Alcott’s beloved book about the four March sisters and their mother, Marmee (Susan Sarandon), who fend for themselves in New England when their father is off fighting in the Civil War, has everything going for it. A terrific ensemble of actors male and female, a smart and moving script that revolves around women’s  issues, some genuine tear-jerking moments  and just the right actress to play Jo, the passionate wannabe writer who pens plays for her three sisters to perform. Not only does Ryder exude an aura of intelligence and strength onscreen but she isn’t afraid to be vulnerable, either, as  her character defines what she wants in life. That she is the only actress so far to be Oscar-nominated for Best Actress as Jo, previously embodied by Katharine Hepburn in 1933 and June Allyson in 1949. This version also was nominated for its score and costumes.

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