The Stunning Transformation Of Winona Ryder

Winona Ryder rose to fame playing the quintessential teen outsider in the 1980s and '90s in iconic movies such as "Beetlejuice" and "Heathers," and is often touted as a Generation X icon, per Newsweek. The brunette actor wasn't always popular or seen as stylish, though. After finding her comeback success in 2017 with the Netflix series "Stranger Things," Ryder told Marie Claire she was bullied as a child and hoped becoming an actor would make her life easier at school. Instead, it made the bullying worse. 

Ryder explained to People in 2017 that she was often targeted because she had short hair, a small frame, and wore boy's clothing. "I was wearing an old Salvation Army shop boy's suit," Ryder told her biographer, Nigel Goodall, for the book, Winona Ryder: The Biography. "As I went to the bathroom I heard people saying, 'Hey, f*ggot [a homophobic slur].' They slammed my head into a locker. I fell to the ground and they started to kick the s**t out of me. I had to have stitches."

Aside from the bulling, though, Ryder's childhood was fairly positive. Keep reading for more details on her stunning transformation.

Born Winona Laura Horowitz in 1971 in Winona, Minnesota, Winona Ryder had a less-than-elegant childhood, but it was full of love. She told Marie Claire in 2017 that her family was poor when she was growing up, so her parents — both writers — compensated with love and affection. She was raised on a commune in California, where her parents were friends with poet Allen Ginsberg. Ryder's godfather was another creative:  writer Timothy Leary. "There's that saying, 'you find your family,' but I would have chosen them even if they weren't my parents," she told the publication. "They're my best friends."

Her parents were wary of allowing her to try acting, insisting she could only pursue the hobby as long as she kept her grades up. They even refused to allow her to film during school hours. Ryder's first role was in the 1986 film "Lucas" with Corey Haim and Charlie Sheen, per IMDb, but it wasn't until her third role — as the rebellious teenage goth Lydia in 1988's "Beetlejuice" — that she became well-known in Hollywood. 

Only 17 years old at the time, the budding actor thought starring in a blockbuster movie would end the bullying she endured at school. "I remember thinking, 'Ooh, ["Beetlejuice"] is like the No. 1 movie. This is going to make things great at school,'" she told Marie Claire. "But it made things worse. They called me a witch."

Winona Ryder was one of the hottest young actors in the late 1980s, finding her niche by playing characters who were overly self-conscious and awkward, which she could relate to in real life. According to a Rolling Stone interview from 1994, she described herself as a "cheesy, tacky, nervous, geeky, defensive, pampered, privileged midget freak." However, her "Reality Bites" co-star Janeane Garofalo said any quirky qualities Ryder had made her all the more likable. "I've noticed that even little, little kids like her," Garofalo said. "I think Winona's the poster girl of every Trekkie, every computer nerd, every information-superhighway addict, every comedyhead and every comic-book collector. And athletes, too. You know? She's so gorgeous that she crosses over."

After roles in hit films such as "Great Balls of Fire," "Heathers," "Dracula," and "Reality Bites," Ryder also found critical success, winning a Golden Globe for Best Supporting Actress for her role in "The Age of Innocence" and an Academy Award nomination for playing Jo in "Little Women." 

Even though they ultimately weren't meant to be, Winona Ryder and Johnny Depp had a four-year relationship that was definitely memorable (via Distractify). They met in 1989 during the film premiere of "Great Balls of Fire." According to a 1991 interview with Rolling Stone, Depp said he felt sparks even though they'd only glanced at one another briefly in the lobby. Soon after, a mutual friend of the pair took the "Stranger Things" star to Depp's hotel room, where he finally asked her out on a date. Just months later, Depp proposed. At the time, Depp said, "There's been nothing ever throughout my 27 years that's comparable to the feeling I have with Winona."

Later in 1990, the well-liked couple starred together in "Edward Scissorhands," with Ryder playing the love interest of Depp's character. As their romance continued, Depp got "Winona Forever" tattooed on his arm. Still, despite the pair's seemingly blissful engagement, Ryder and Depp broke up in 1993. The reason for their split was never officially announced, but Depp later suggested during an interview with the Los Angeles Times that the media had something to do with the breakup.

Shortly after Winona Ryder's relationship with Johnny Depp ended in 1993, she met Soul Asylum's Dave Pirner (via The Manhattan Mercury). By the end of that year, the "Beetlejuice" actress moved into Pirner's home in Minneapolis, Minnesota. While the outlet noted that Ryder's relocation didn't receive much attention, they added that the same couldn't be said for her relationship. The pair would later break up sometime around 1997.

Then, of course, there was Ryder's relationship with fellow actor Matt Damon. As stated by Yahoo!, the pair were allegedly introduced to one another in December 1997 by Gwyneth Paltrow. Despite the stars ' high-profile status, the couple managed to keep their relationship private. However, after two years, the pair called it quits in 2000. Despite fizzling out, there would appear to be no hard feelings between the former flames. During a 2004 interview with Playboy, Damon had nothing but nice things to say about Ryder. She did the same during a chat with BlackBook, saying, "Matt couldn't be a greater, nicer guy. I'm really lucky that I'm on good terms with him."

While Winona Ryder isn't interested in rushing down the aisle, it sounds like the star might have accidentally gotten married due to a technicality. It's possible that Ryder and her former co-star Keanu Reeves got hitched in the '90s while the pair were filming "Dracula." As fans of the iconic bloodsucker are well aware, in Francis Ford Coppola's retelling of Bram Stoker's famous tale, Ryder's Mina and Reeves' Jonathan marry in the film. According to the outlet, Coppola went all out in terms of authenticity and used a real Romanian priest to make it official for the characters and possibly for the actors.

"We actually got married in Dracula. No, I swear to God I think we're married in real life," Ryder joked to Entertainment Weekly. While Reeves (who was also present for the chat with EW) initially joked about his co-star's statement, he eventually agreed that their onscreen marriage was possibly the real deal. Similarly, while speaking with Esquire, the "Matrix" star again addressed the rumors of perhaps tying the knot with Ryder. "We did a whole take of a marriage ceremony with real priests," Reeves said. "Winona says we are [married]. Coppola says we are," the actor quipped before adding, "So I guess we're married under the eyes of God."

In 1999, Ryder opened up about dealing with anxiety and depression in an interview with Diane Sawyer. Not long after, was arrested on suspicion of shoplifting in December 2001 and was simultaneously found with numerous prescription drugs, according to Biography. Ryder later told The Cut in 2016 that it was a rough period for her, and she temporarily gave up acting because of the intense public scrutiny that followed. She said the stigma of battling depression and anxiety meant she developed a reputation for being crazy, which felt unfair. "Even that word, 'anxious,'" she told the publication. "It's a bad word. And so like all of these words — it's kind of what I tried to do with 'Girl, Interrupted,' and why I was so invested in that book and trying to get it made [as a movie]. My whole point was, this happens to every girl, almost."

Ryder said she wanted to help remove the stigma of depression and anxiety by revealing her struggle to Sawyer on television, but it only added to her internal struggles and changed the way people viewed her. "I think by doing that, maybe coupled with my physical size, there's this 'crazy' thing," she told The Cut. "And I've realized recently it's literally impossible to try to change that story."

Winona Ryder returned to acting in 2006, starring in "A Scanner Darkly" before being cast as an embittered, aging dancer in 2010's "Black Swan," per IMDb. However, she wouldn't find herself in a major spotlight again until she debuted as Joyce Byers in the Netflix mega hit "Stranger Things" in 2016. 

She told Marie Claire she also consulted her own mother to prepare for "Stranger Things." In the series, Ryder plays a single mother of two whose youngest son goes missing. Surrounded by a cast of young actors who suddenly became famous, Ryder admitted she worried about them all growing up in the spotlight. "Millie [Bobby Brown, who plays the enigmatic Eleven] teases me," she said. "I'm like the old grandma." She laughed, sharing a story about how she mistakenly thought someone said "snack" when referencing the Snapchat messaging app. "'Snack chat? Give me a piece of that!' I'm like the confused older person [on the set]," she said.

Even through her rough patches, it seems like Ryder never lost her passion for her craft, and is being rewarded for it today.

While Winona Ryder definitely has a fascinating dating history, New York Gal reports that the star enjoys a relatively private relationship with designer Scott Mackinlay Hahn. While it's still unclear exactly how the two met, some have alleged that it was through their mutual friend U2 singer Bono. Still, regardless of how these two lovebirds came together, their relationship has been going strong since 2011.

Still, though the pair seems like the ultimate couple, it sounds like Ryder has no interest in tying the knot anytime soon. According to an interview with Net-A-Porter, while the "Dracula" star is "a serial monogamist," she's hesitant about switching her status from Ms. to Mrs. because she sees marriage as a serious commitment. "I'd rather never have been married than been divorced a few times," she stated. But, of course, this choice appears to work for the happy couple.

During a 2014 interview with The Telegraph, Winona Ryder revealed some details about her personal life. After showing off a video of her goddaughter, the actress opened up about her view on having children. "This is a little personal, but I'm 42 and ... Well, I was talking to my dad last year and saying, 'What if I can't have a kid?'" Still, despite her worries, Ryder said her father reminded her that "there are other ways to have children in your life." The star then admitted that she gets plenty of love from her brother's kids.

More recently, the "Black Swan" star spoke to The Cut and revealed that she often gets questioned about how she portrays Joyce on "Stranger Things." Ryder stated, "I'm getting asked a lot, 'You don't have kids, so how do you know how to act like a mother?" She then explained how she connects with her character, saying, "I know nothing could compare, and I haven't had that experience, but when my niece was born, I felt like I would jump in front of a car and die for this little person I didn't even know yet." However, the actor added that she could also feel intense compassion for the character and how her life played out, noting that Joyce is a complex but relatable woman.