- Suffers from insomnia. She allegedly has had a habit of talking on the phone with actor Al Pacino, who also suffers from insomnia.
- Audrey Hepburn used to send her clothes.
- Wanted to be a competitive skateboarder when she was younger.
- Is admittedly a late bloomer in terms of electronic devices. She did not know what streaming was, when she was approached to do the Netflix series Stranger Things (2016).
- Her agent begged her not to do the comedy Heathers (1988), saying her career would be over.
- Broke her arm during the filming of Mr. Deeds (2002), in the scene where she and Adam Sandler are riding bikes down a flight of stairs.
- She owns some of Hollywood's stars' most priceless possessions (Louis Armstrong's bongo drums among others). She also has a collection of vintage Hollywood costumes, including Russ Tamblyn's jacket from West Side Story (1961), Leslie Caron's dress from An American in Paris (1951), Claudette Colbert's gown from It Happened One Night (1934), Olivia de Havilland's blouse from Gone with the Wind (1939), and Sandra Dee's bikini from the "Tammy movies".
- She dedicated the film Little Women (1994) to Polly Klaas, a young girl from her hometown of Petaluma, California, who was kidnapped and brutally murdered. She offered a $200,000 reward for anyone with information on the subject, and remains a strong supporter of the Polly Klaas Foundation.
- According to director Francis Ford Coppola, much of the cast for Bram Stoker's Dracula (1992) was assembled as Winona's "dream cast".
- She was ready to play Jupiter "Joon" Pearl in Benny & Joon (1993) and at the time was dating Johnny Depp. She dropped out of the project upon her break-up with Depp. The role eventually went to Mary Stuart Masterson.
- Suffers from aquaphobia because of trauma she suffered at age 12 when she nearly drowned. This caused problems when she had to act in some of the underwater scenes in Alien Resurrection (1997). The scenes had to be reshot numerous times because of this.
- She briefly checked herself into a hospital when she was age 20, because she was suffering from depression, anxiety attacks and exhaustion, resulting from constantly working on films.
- Dropped out of The Godfather Part III (1990). She said in an interview later that year that she arrived in Rome to film and simply could not get out of bed. A doctor was called and ordered her to return home and sleep.
- Although there was no electricity on the commune where they resided, when Winona was seven, her mother began to manage an old movie theater in a nearby barn and would screen movies all day. She allowed Winona to miss school to watch movies with her.
- She was harassed her first week of junior high school when a group of bullies mistook her for an effeminate, scrawny boy. Ryder said she came to school in Salvation Army clothes and one of the bullies cried out "Hey, faggot!" They charged her and beat her down. She was injured so badly, she needed stitches. She was expelled from the school for her own safety. She was then home-schooled from thereon inside.
- Her real hair color is blonde but when she made her first major film Lucas (1986), her hair color was dyed black. She was told to keep it that color and with the exception of Edward Scissorhands (1990), it has stayed that color since.
- When she was residing with Johnny Depp in 1991, he once sent 200 packets of her favorite food, Oriental-flavored Ramen noodles, to her hotel room when she was away working on a film.
- When Joyce Maynard released private letters from J.D. Salinger to the public for an auction, Ryder bid on them in hopes of sending them back to Salinger to honor his privacy or to ignite them if he did not wish to keep them. Salinger is one of her favorite writers.
- Angelina Jolie thanked her in her Oscar acceptance speech when she won 'Best Actress in a Supporting Role' for Girl, Interrupted (1999), adding that "Winona, you're amazing and thank you for supporting all of us through this.".
- Is six years older than her Star Trek (2009) co-star Zachary Quinto, who plays her son in the movie. She was cast as Spock's mother Amanda because the opening scene originally featured her giving birth to Spock. However, the scene was deleted and replaced with a more action-packed scene. Incidentally, Captain James T. Kirk's mother in the movie is named Winona.
- Had dated Johnny Depp for many years. His original tattoo of her read: "Winona Forever". After they broke up, he had this reduced to "Wino Forever".
- She turned down the role of Katrina Van Tassel in Sleepy Hollow (1999), which went to Christina Ricci.
- Persuaded Universal Pictures to turn the February 1994 Los Angeles premiere of Reality Bites (1994) into a benefit for the Polly Klaas Foundation. She also had enough clout to see that Louisa May Alcott's "Little Women" - Polly's favorite book - was made into Little Women (1994), with Winona in the title role and the film dedicated to Polly Hannah Klaas.
- On December 12, 2001, she was arrested in Beverly Hills for allegedly stealing clothing items and carrying illegal pharmaceutical drugs without a prescription. Her lawyer denied the accusations, and Winona was released later that evening on $20,000 bail. Despite her alleged crime, Beverly Hills police described her as "very friendly, polite and cooperative" and "a nice lady".
- She pitched Bram Stoker's Dracula (1992) to Francis Ford Coppola. She had been given a pile of scripts by her agent, one of which was titled "Dracula: The Untold Story". This was the first time Ryder had ever read anything to do with Dracula, let alone see a film about him. She gave Coppola the script, when they met to discuss a possible adaptation of Jack Kerouac's "On the Road". Coppola was interested in Dracula as he saw this as a bridge-building exercise between him and Ryder after she had inexplicably dropped out of The Godfather Part III (1990).
- She serves on the Board of American Indian College Funds.
- In 1995, she made yet another significant artistic departure, recording a spoken word reading of the famous diary of Anne Frank, for which she received a Grammy nomination. Winona became one of the few non-musicians to have been nominated for both an Oscar and a Grammy for different projects.
- Good friends with Courtney Love and the late Brittany Murphy.
- Attended and graduated from Petaluma High School in Petaluma, California with a 4.0 GPA (1989).
- Took her last name "Ryder" from Mitch Ryder, the lead singer of Mitch Ryder & The Detroit Wheels. She saw one of his albums in her father's record collection.
- She was announced as the new face of Marc Jacobs Beauty for the label's spring/summer 2016 campaign. She and the label's owner, Marc Jacobs have been close friends for years. (December 2015)
- Has appeared on the cover of the June 2002 cover of W magazine wearing a "Free Winona" T-shirt. "Free Winona" T-shirts became popular over the Internet following her December 22, 2001 arrest, with many fans sporting them and purses in support.
- Began work on Girl, Interrupted (1999), which took four more years to succeed to the screen (1996).
- She was awarded a Star on the Hollywood Walk of Fame at 7018 Hollywood Boulevard in Hollywood, California on October 6, 2000. She was voted Best Dressed Celebrity of the Week by Entertainment Weekly for the event. Her great friend Sir Anthony Hopkins attended the ceremony.
- She was Martin Scorsese's first and only choice for the role of May Welland in The Age of Innocence (1993). For years, she kept the message she left on her voicemail, informing her she got the role.
- On August 16, 2001, she suffered severe stomach pains and doubled over in pain. She was sent to her hotel room in London, England, and later was admitted to the hospital and diagnosed with a severe gastroenterological disorder. She left the United Kingdom on August 24th. The sickness caused her to drop out of the (unreleased) film Lily and the Secret Planting (2002) and her role eventually went to Kate Winslet instead. Winona was said to have been very passionate about her role in the film and was heartbroken to leave. The incident brought to mind the similar 1990 stomach flu that caused her to drop out of The Godfather Part III (1990) two days before filming began, causing a great deal of controversy.
- Is an avid reader of 1960s literature (Allen Ginsberg, Jack Kerouac), but also F. Scott Fitzgerald, Jane Austen, Aldous Huxley, Oscar Wilde and many more. Her all-time favorite book is "The Catcher in the Rye" by J.D. Salinger.
- Had done her own singing in the animated horror comedy Frankenweenie (2012). She agreed to do this when director Tim Burton said this had to sound imperfect.
- She turned down the lead role in Sydney Pollack's Sabrina (1995) because she felt she could not fill Audrey Hepburn's shoes and that the role was marked by sexism.
- Winona's father is from a Jewish family (from Russia and Romania). Her mother has Belgian, English, German and Irish ancestry. Winona's mother's maiden name, Istas, is Belgian.
- Her father's family was originally named "Tomchin", however she stated that they were wrongly assigned the name of the family that they were travelling with when they arrived at Ellis Island, in 1906.
- She auditioned for the role of Marla Singer in David Fincher's Fight Club (1999), which eventually went to Helena Bonham Carter.
- Before becoming an established actress, Winona once babysat for Tom Waits, one of her favorite artists.
- Independent filmmaker Jim Jarmusch wrote a role specifically for her in Night on Earth (1991), as a tattooed, chain-smoking cabdriver who dreams of becoming a mechanic.
- Has collaborated with Tim Burton, on film, four times now. There was a 21-year-long gap between their second and third project. They also worked on the music video for the song "Here with Me" by the rock band The Killers (2012).
- She portrays a ballerina in the horror film Black Swan (2010). In real life, she only took several ballet lessons as a child, but gave up because she was intimidated by her teacher.
- Signed onto "The Girl You Want". After a few weeks of preproduction, she received a new version of the script, which she hated, and tried to get out of her contract. Touchstone Pictures threatened to sue her if she did, and so she completed the film. The film's title was changed to Boys (1996) and sat on the shelf for more than a year. After the film finally got its release, it was released in less than 100 theaters in North America and grossed less than five hundred thousand dollars.
- Her December 22, 1999 guest spot on The Tonight Show with Jay Leno (1992) was her second-ever appearance on a talk show. She did it to promote Girl, Interrupted (1999), the first film on which she served as executive producer. She clearly had jitters but settled in comfortably. She made her first appearance on The Oprah Winfrey Show (1986) with Mermaids (1990) co-star Cher.
- She is also into music and plays the guitar. Her favorite band at one point was The Replacements, but she also loves Tom Waits, Cocteau Twins, Wilco and many others.
- Cut her eyelashes for her role as a city council woman in Show Me a Hero (2015) after writer David Simon sweet-mannered said they made her look too endearing.
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