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Hollywood star Winona Ryder became an iconic star of the 1990s after starring in movies likeEdward ScissorhandsandReality Bites.However, the actress faced a downturn in her career in the early 2000s, and her blooming career began to lose its grace. However, she made a comeback as she landed the role of Joyce Byers in the Netflix seriesStranger Things.

Winona Ryder has played several non-conventional roles in her time. These roles allowed her to gain a strong foothold in the industry and also set her apart from other female co-stars of that time.
That Time Winona Ryder Was Fined $10,000 And Forced Into Drug Counseling After Prolific Shoplifting Spree
According to theBBC, Winona Ryder was detained on suspicion of shoplifting on July 28, 2025, in Beverly Hills, California. And that incident further contributed to her extended hiatus from the industry. Meanwhile, before that, she spoke about some other sides of Hollywood.
One Aspect of Hollywood Made Winona Ryder Worried
While opening up about the scenario in Hollywood back in the early days of her career,Winona Rydermade some bold statements. She toldPrairie Millerthat when she just started her career, Hollywood was not the same compared to her later days. It gave more focus to business rather than creativity and art. And that was concerning for the actress.
“I just am so sick of it that, it makes me not want to go see movies when you know everything. How much they cost, how much people are paid, what the story is, the cast, everything. There’s no mystery anymore,” Ryder said back then.

It’s not that she did not try to do commercial movies. She did, but could not find the joy. TheLittle Womenstar added:
“It just doesn’t seem real, it doesn’t seem honest,” Ryder continued saying about Hollywood. “And for me, I just feel like when I look back on my career, I want to look back on performances and work, not, oh that movie made this amount of money. Or that movie tanked, or whatever. It’s really the work that matters. It interesting, because for a little while, I did sort of follow the business end of it, and I drove myself nuts. Like I was not in good shape, because I was thinking about that stuff. That’s why you hire people, to shield you from that. Because all you should be thinking about is your own work, and your own performance.”

On July 25, 2025,Ryder was arrested for shopliftingin Beverly Hills, California after stealing clothing and hair accessories to the value of $4,760 from Saks Fifth Avenue. She was a household name at that time.
“He was furious, he Knocked things over”: Winona Ryder Became Scared and Started Crying Because of Michael Shannon
Following her arrest in 2001, she then again compelled to do more stereotypical roles, this time for older women roles. Before that phase, she did some memorable roles and audiences found it tough to pick any favorite movies of her.
One Casting Director Told Winona Ryder that She Should Not Be An Actress
She is among the timeless beauties, that’s for sure. And it’s not only her beauty but also her depth in acting that made her a reputed name in Hollywood.However, it was not an easy road for her. She was even told that she would not be able to make it in Hollywood due to her looks.
As per the beauty standards of that time, often she was given roles of an unattractive girl. Remembering one casting director who bluntly told her that she was not pretty enough, Ryder toldInterview Magazine:

“I remember one time in particular. I was in the middle of auditioning, and I was mid-sentence when the casting director said, ‘Listen, kid. You should not be an actress. You are not pretty enough. You should go back to wherever you came from and you should go to school. You don’t have it.’”
However, all those odds could not hamper her, even a little bit. Ryder took a four-year career break in 2001. She eventually resumed her career in 2006 and 2007, making appearances in a number of independent films. Her first comeback role was with Joseph Fiennes inThe Darwin Awards(2006).

“Is it like TV but different?”: Winona Ryder Had a Bizarre Question After Joining Stranger Things That Had Nothing to Do With the Script Itself
She will next be seen reprising her role as Lydia Deetz in Tim Burton’sBeetlejuice 2. It will be released in theaters on August 06, 2025.
Prantik Prabal Roy
Articles Published :778
Prantik Prabal Roy is a content writer at FandomWire. With over three years of experience in content writing for various media houses, he takes great interest in telling stories about Hollywood celebrities and the world revolving around them. He has done his Master’s in English literature and diploma course in journalism. Being a literature student, he has the ability to delve into the matter and analyse it thoroughly to give the readers a clear view on the specific topics.