Comeback queen! Winona Ryder was the “It girl” of the ‘90s, and after a hiatus from the industry, she proved she could still hold her own years later.
The actress was born Winona Horowitz on October 29, 1971. She landed her first role in the 1986 film Lucas at age 14, which led to her being cast in 1988’s Beetlejuice by the time she was 17. From there, her career skyrocketed with parts in 1988’s Heathers, 1990’s Edward Scissorhands, 1994’s Little Women and more.
Soon, Ryder felt the pressure of being a Hollywood A-lister. “There were times where people might have seen me and said, ‘Wow, she’s so lucky.’ But I was depressed, I was going through something,” she told Time in June 2016. “That time I went through led me to make Girl, Interrupted. Most girls go through that at around that age — 20, 21.”
The Stranger Things star poured herself into the 1999 film, but her career stalled anyway. “You can’t look to the industry to validate you as a person because that can just lead to incredible disappointment,” she noted. “I will admit I was guilty of that when I was younger because you get caught up in it, surrounded by people that are telling you that it’s the most important thing, and you’re young and you believe it.”
Ryder found herself overtaken by a scandal in 2001 when she was arrested for shoplifting. She subsequently retreated from the spotlight, sharing with Time years later that it was “really important for me to get out.”
The Oscar nominee used the time to grow without the eyes of the world watching her. “I took some years off, and I didn’t realize that was very dangerous in terms of my career. I was constantly being told, ‘You have to keep working so you stay relevant.’ When I was ready to come back, I was like, ‘Oh, where did everyone go?’” she recalled. “A lot of actors have ups and downs. I think mine were — people might see them as awful — but I learned, and I appreciated the time away.”
Ryder referred to her 30s as “a little bit tough” because she was typecast as an “ingénue.” However, she eventually broke through the stereotypes and booked her role on the Netflix hit Stranger Things.
“I started acting so young, I secretly wanted to be older,” she explained to Time. “I know there’s a lot of conversations right now about ageism, and I know a lot of actresses who have a tough time, and I’ve gotten offered those mom parts. But you can make something of it. For me, I’m finally getting to play my own age, and it’s liberating. I would not want to go back to playing the ingénue.”
Scroll through the gallery below to see Ryder’s life in photos.
1988
Ryder landed her breakout role in Beetlejuice when she was still a teenager. The film served as a launch pad for her acting career.
1989
The Minnesota native made an impression as the murderous Veronica Sawyer in the cult classic Heathers.
1990
Ryder got engaged to her Edward Scissorhands costar Johnny Depp in July 1990, but they called it quits after three years. She defended the actor decades later when his ex-wife Amber Heard accused him of abuse — allegations he repeatedly denied.
“I truly and honestly only know him as a really good man — an incredibly loving, extremely caring guy who was so very protective of me and the people that he loves, and I felt so very, very safe with him,” the Star Trek actress said in a 2020 witness statement.
1990
Ryder starred alongside her then-boyfriend, Depp, in Edward Scissorhands as he took on the titular role.
1993
The Reality Bites actress earned her first Academy Award nomination for her work in Martin Scorsese’s 1993 period film, The Age of Innocence. Although she did not win the Oscar, she took home a Golden Globe for Best Performance by an Actress in a Supporting Role in a Motion Picture.
1994
Back-to-back nods! Ryder received her second Oscar nomination for her star turn as Jo March in the 1994 adaptation of Little Women.
1998
The Show Me a Hero alum dated Matt Damon from 1998 to 2000. “Matt couldn’t be a greater, nicer guy,” she told BlackBook in 2009. “I’m really lucky that I’m on good terms with him.”
1999
Ryder worked as an actress and executive producer on Girl, Interrupted, shepherding the project for seven years before the film made it to theaters. Her costar Angelina Jolie earned an Oscar for her portrayal of a woman suffering from mental illness.
2001
As her career slowed down, the Dracula star was arrested in December 2001 for shoplifting $6,000 worth of merchandise from Saks Fifth Avenue. Police also found a syringe and painkillers in her possession. She was convicted of grand theft, shoplifting and vandalism and sentenced to three years of probation, 480 hours of community service, $3,700 in fines, $6,355 in restitution to Saks Fifth Avenue and psychological and drug counseling.
2010
After taking a hiatus from acting amid her shoplifting scandal, Ryder gradually returned. She proved she still had the chops when she portrayed an aging ballerina in 2010’s Black Swan.
2011
The Autumn in New York star began dating fashion designer Scott Mackinlay Hahn in 2011. The couple’s relationship remains very low-key, but she told PORTERedit in July 2016 that she has “been happily with someone for quite a while.”
2016
Ryder solidified her comeback with a role on Stranger Things, which became a runaway success when it premiered in July 2016. She received a Golden Globe nomination in 2017, and the cast won Outstanding Performance by an Ensemble in a Drama Series at the 2017 Screen Actors Guild Awards.
2020
The Friends album continued to redefine herself in the HBO limited series The Plot Against America.
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