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Top 10 Winona Ryder Films

Rachelle is an IT college enrollment counselor, tech geek and typical, garden variety nerd who also loves books, films & all things Gen X.

Winona Ryder

Winona Ryder

Winona Laura Horowitz was born October 29, 1971 in Winona County, Minnesota. She is known professionally as Winona Ryder, the quirky actress who won our hearts decades ago.

Ryder was initially known for playing eccentric characters throughout the 90s, but she has since grown into one of the most accomplished and most recognized entertainers in Hollywood and beyond.

She has garnered multiple accolades and she is currently enjoying a resurgence in popularity due to her role as Joyce Byers on the supernatural TV series, Stranger Things (2016 - )

In short, audiences love the actress and many people cannot get enough of her; if you are in that camp, here is my pick for the top 10 Winona Ryder movies.

Winona Ryder as "May" in The Age of Innocence (1993)

Winona Ryder as "May" in The Age of Innocence (1993)

1. The Age of Innocence (1993)

The Age of Innocence (1993) has been described as being "excellence on a grand scale." The film tells the story of attorney Archer Newland (Daniel Day Lewis) in 19th Century New York. He is engaged to marry the prim, proper and privileged socialite May Welland (Winona Ryder).

The couple enjoys a quiet lifestyle, which is disrupted when May's unorthodox cousin Ellen (Michelle Pfieffer) arrives. Newland defends Ellen as she attempts to escape an abusive marriage.

Ellen's separation from her husband makes her a social pariah in their high society circle, but Newland finds himself romantically drifting towards Ellen.

The film is the other one of two films where Ryder's performance was nominated for an Academy Award. The Oscar nod is due to her masterful portrayal of a girl who morphs from an innocent young lady into a mature young woman with manipulative control over her partner.

Winona Ryder as "Susanna" in Girl, Interrupted (1990)

Winona Ryder as "Susanna" in Girl, Interrupted (1990)

2. Girl, Interrupted (1999)

Set in the tumultuous and changing world of the late 1960s, Girl, Interrupted is based on the true story of Susanna Kaysen (Ryder).

Susanna is a young woman who finds herself at a renowned mental institution for troubled young women, where she must choose between the world of people who belong on the inside and the outside world.

The fact that Susanna has the option to choose is major point to the film as many of the other young women she shares a ward with do not have the same luxury. However, only she has the power to change her situation.

Winona Ryder as "Jo" in Little Women (2006)

Winona Ryder as "Jo" in Little Women (2006)

3. Little Women (2006)

Little Women (2006) is a film version of Louisa May Alcott's autobiographical account of her life with her three sisters growing up in Concord, Massachusetts in the 1860s.

The sisters, Jo, Meg, Amy and Beth (Ryder, Trinia Alvarado, Kirsten Dunst & Claire Danes) live at home with their mother, Margaret (Susan Sarandon), who is an outspoken woman for her day, while their father is off fighting in the American Civil War.

The sisters mature into women, find love and their place in the world. Winona Ryder plays Josephine "Jo" March, an ambitious young woman, who aspires to become a successful author.

I included this film on this list because it has thus far been one of two of Ryder's most critically acclaimed roles. It is a decent film and the actress shines here, but as all things go...the book is better.

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Wynona Ryder as "Donna" in A Scanner Darkly (2006)

Wynona Ryder as "Donna" in A Scanner Darkly (2006)

4. A Scanner Darkly (2006)

In a not-too-distant, totalitarian future, the U.S. has lost its war on drugs. Substance D has taken ahold of 20% the country, it is a powerful drug that causes bizarre hallucinations.

Robert Arctor (Keanu Reeves) is an Orange County narcotics cop who becomes an addict as he goes undercover in a high tech world of shifting identities and cloaking suits.

Arctor's job is to woo Donna, (Ryder) a drug dealer, to get to her supplier. He is also charged with the additional task of spying on his housemates, Luckman (Woody Harrelson) and Barris (Robert Downey, Jr.) as one of them is suspected of being Donna's biggest customer.

A Scanner Darkly (2006) is a highly stylized animated film that is said to be akin to taking a bad trip, but one well worth taking—just so long as you can keep your thoughts straight during the movie and you're able to find your way back to clarity afterwards.

Ryder rocks in this film, as do all of the other A-list actors in tow.

Winona Ryder as "Lydia Deetz" in Beetlejuice (1988)

Winona Ryder as "Lydia Deetz" in Beetlejuice (1988)

Quintessential Ryder at her Quirky Best

In this category, I have listed three movies where Winona Ryder performs in roles that perfectly display her signature 90s era quirky appeal.

These are the roles that first endeared her into the hearts and minds of Generation X and the ones in which we remember her fondly:

5. Beetlejuice (1988)

The spirits of a deceased couple are harassed by an obnoxious family that has moved into their home, which they haunt, so they hire a malicious spirit (Beetlejuice) to drive them out.

Ryder appears here as Lydia, the family's serious, but kind girl who is sensitive despite her goth appearance and she feels isolated in the world.

6. Heathers (1989)

A teenage girl, Veronica Sawyer (Ryder) teams up with a sociopath and plots to kill the snobbish high school clique (all named Heather) that threatens to ruin her reputation.

The film is a black comedy, meant to be the exact opposite of the feel-good teen films of the 80s, John Hughes/Molly Ringwald-esque era.

7. Edward Scissorhands (1990):

Here, Ryder portrays Kim Boggs, the girl who eventually falls in love with Edward. While her role here is not necessarily one of a quirky nature, the film itself is the epitome of quirkiness.

This is the second film collaboration of director Tim Burton and Winona Ryder, the first was Beetlejuice (1988) and the third is the animated film Frankenweenie (2012).


Winona Ryder and Christina Ricci in Mermaids (1990)

Winona Ryder and Christina Ricci in Mermaids (1990)

8. Mermaids (1990)

In Mermaids (1990), Ryder plays Charlotte Flax, a 60s era teenager who is being raised by her unconventional single mother (Cher), along with her younger sister (Christina Ricci).

The family moves to a small town in Massachusetts where a string of events test and strengthen their familiar bond. In this film, Winona Ryder's character is quite different from her usual fare as Charlotte actually longs to be "normal."

Winona Ryder as " Lois Wilson" in When Love Is Not Enough: The Lois Wilson Story (2010)

Winona Ryder as " Lois Wilson" in When Love Is Not Enough: The Lois Wilson Story (2010)

9. When Love Is Not Enough: The Lois Wilson Story (2010)

In 1914, Lous Burnham (Ryder) is an educated woman who hails from an affluent family. She meets and marries Bill Wilson (Barry Pepper), a man of modest means, and they settle into a life together.

As time goes by, Louis finds her way as a nurse while Bill struggles to find his way. Over time, he becomes an alcoholic and drives the couple to the brink of ruin.

On his eventual road to sobriety and with the aid of a fellow alcoholic, Bill co-founds Alcoholics Anonymous in 1935. Meanwhile Lois endures years of neglect and mistreatment from Bill due to his addiction and recovery, which does not include her.

Feeling angry and isolated, Lois comes to discover that there are many others who feel the same way after witnessing their loved ones succumb to alcoholism, and this leads her to co-found Al-Anon in 1951.

The movie was given mixed reviews by critics, but overall the story & history is interesting and Ryder does a good job of playing a woman who puts up with much more garbage than a modern woman ever would.

Winona Ryder & Gary Oldman as "Mina Murray" and "Count Dracula" in Bram Stoker's Dracula (1992)

Winona Ryder & Gary Oldman as "Mina Murray" and "Count Dracula" in Bram Stoker's Dracula (1992)

10. Bram Stoker's Dracula (1992)

Rounding out this list of Top 10 Winona Ryder movies is the 1999 Francis Ford Coppola directed gothic horror film, Bram Stoker's Dracula. Here, Ryder plays Wilhelmina "Mina" Harker (née Murray) opposite Keanu Reeves' Johnathan Harker.

Johnathan journeys to Transylvania, where he encounters the vampire Count Dracula (Gary Oldman) and his Brides at Bran Castle.

Eventually, the vampire makes his way to London where he encounters Mina and he falls in love with her as she is the spitting image of his centuries dead wife. The Count immediately moves to turn her into one of the undead and the classic story unfolds from there.

There have been many filmized version of Bram Stoker's engaging tale, but this movie's use of atmospheric cinematography and over-the-top performances by Gary Oldman, Anthony Hopkins, and Tom Waits places it far and away above any other version.

It was Winona Ryder who brought the story to the legendary filmmaker and from there Coppola turned it into a masterpiece that reveals both the horror and the romance of the story.

© 2022 Rachelle Williams

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