Ray William Johnson: True Story Podcast - This Stranger Things Star Has a Dark Past - The Winona Ryder Story

Episode Date: November 28, 2025

Actress Winona Ryder was caught stealing more than $5,000 worth of designer clothing and accessories from Saks Fifth Avenue in Beverly Hills. Security detained her after observing her cutting sensor tags and walking out with the merchandise, leading to her high-profile arrest and a media frenzy that dominated early-2000s pop culture.

Remember when this Stranger Thing star got arrested for stealing? Because I do. Now, of course, I'm talking about this woman, Winona. And Winona is around 30 when this story starts, and she's living in Hollywood, and she's a very popular actor during this time. You saw her in Beetlejuice, you saw her in Little Women, she was also in Edward Cisorhands, a bunch of stuff. She got a star on the Hollywood Walk of Fame.

She's even been nominated for an Oscar, not once, but twice. So she's clearly doing really well. However, Winona has a problem. It seems like the fame might be getting to be too much for her. Maybe sometimes she just wishes it would stop. Because she's not in a good place. Like she's suffering from depression and anxiety attacks. So eventually she admits herself into a psychiatric ward hoping to get some help.

But she doesn't seem to get the help she needs, I guess, because soon she leaves rehab and goes. right back to making more movies. But then, one day, in 2001, she gets hurt. She's actually on set filming a movie with Adam Sandler called Mr. Deeds, and in one scene, she's riding a bike when suddenly, bam, she falls, and she breaks her arm. So she ends up seeing a doctor to get it fixed. And she's in a lot of pain, so the doctor prescribes her painkillers.

Lots of them. And Winona likes these pain killers. She likes them a lot, like they make her feel better. And pretty soon, she's become dependent on them, which causes her to be spaced out a lot of the time. Now, the general public doesn't know this at the time. They just know that she's a famous movie star. But they're about to find out about these painkillers because Winona is about to become more famous than she's ever been. And it starts that same year, 2001, when she goes on a little shopping trip to Beverly Hills,

to a luxury department store called Sacks Fifth Avenue. And you can see her in the security footage here, and she brings in some very large bags with her. And she walks around the store, and she grabs a ton of clothes to try on. Then she goes into the dressing room with all that stuff, and in there she pulls out a pair of scissors from her purse, and she starts cutting off the security tags. And then she stuffs all those clothes into her bags, and she walks out of the dressing room, and those bags she brought with her are noticeably fuller. Then she walks around the store and hides the loose security tags in pockets of other coats that are for sale.

And at one point, I guess she just abandons her original plan and she just straight up starts shoveling clothes into her bags. Now, what Winona doesn't know is that during all this, she had captured the attention of security who were watching her and recording her every move. And eventually she tries to leave the store and you can see security following her and they catch up to her. and they make her come back inside and they start searching through her bags. And they find a ton of unpaid items with the security tags all cut off, including a $200 hat, a $500 purse, a $700 cashmere sweater, $600 worth of hair accessories. In total, Wynona had tried to shoplift over $5,000 worth of items. And so the store security calls police and bam, she gets arrested.

And I don't have a mugshot, but here is a picture of her and Johnny Depp when they were dating. Now, the shoplifting isn't actually the only thing she gets busted for, because police also searched through her bags and they find her most valuable items yet. A ton of pain killers. In fact, in total, police find eight different types of painkillers in her bag. So on top of theft and burglary charges, she's also hit with drug charges. Now, she's a major movie star. So when news of this multi-millionaire celebrity caught shoplifting gets out, it's like a bomb goes off.

The media is all over this story. Suddenly, Winona is on the news and on the cover of magazines and all these news stations play the security footage of her shoplifting. All the late night TV show hosts are making jokes about her. Some store owners even start putting up these signs in stores, warning them that shoplifting is a crime. I mean, it's like people can't get enough of this story. And so, eventually, Wynonna goes to court over all this. And it's a full-blown media circus, like the cameras are all over her.

Even though the crime committed was just shoplifting. The media treats this like it's O.J. Simpson's murder trial all over again. But the media is not the only ones treating this like it's O.J. Simpson's murder trial. So is the prosecution. See, a few years before this, that, same district attorney's office, the LA County District Attorney's Office, tried to convict O.J. Simpson, and they lost the case, even though O.J. was obviously guilty. So this time, they don't want another celebrity to get away with a crime, nor do they want to look bad again. So they come down

on Wynonna hard. Instead of bumping the charges down to a misdemeanor and giving her like a simple fine, they charge her with four felonies. They also assemble a team of eight-pornment. prosecutors, eight, to ensure that they don't fail and that she's taken down. Now, while all this is going on, do you remember that doctor that overprescribed Winona those painkillers? Well, Winona's drug charges cause prosecutors to open an investigation into him, because it turns out that he was overprescribing painkillers to a lot of rich people and making money off of it. And so, bam, he's busted and he gets his medical license revoked. But this actually ends up helping Wynona because it proves that she was legally prescribed

this medication by a doctor. So the prosecution has no choice but to drop the drug charges against her. Regardless, they continue to go after her for the shoplifting charges. But pretty quickly, going so hard on Wynona starts to backfire on the prosecution. Because by this point, the public is still paying attention. But the novelty of the whole situation. has worn off. And people are like, really? All this over stealing some clothes? And this actually sparks a free Winona movement where stores are selling free Winona t-shirts and apparently people are buying them. Here's Winona herself actually photographed wearing one. And so people clearly feel that she doesn't deserve all the scrutiny she's been getting for this petty crime.

Even Sacks Fifth Avenue, the store that she stole from, said that they didn't want to make make an example out of her and that they wanted out of the media spotlight. But whatever. So they go to trial over this. And when the trial ends, Winona's very expensive legal team is able to make sure that she avoids jail time and only gets probation, community service, some fines, and is ordered to attend psychological and drug counseling.

So that's good for her. However, the damage has already been done. Because now, she's not just a famous. actor, she's also famous for shoplifting. And I mean, she was at her peak and suddenly, boom, she disappears from the spotlight, barely acting at all and only appearing in small roles. And the public nearly forgets about her. Until, 15 years go by, and it's around 2016 at this point. And Netflix is casting for their new show, Stranger Things, set in the 80s.

And they're like, who would be better for this part than the coolest woman from the 80s? And so Wynonna is cast in her first ever TV show that she's ever done ever. And she nails the role and the show is a massive hit. And after that blows up, she gets to reprise her role in Beetlejuice and that's also a hit. And so at the end of it all, Wynonna makes a huge comeback. And she actually says that the shoplifting scandal turned out to be a good thing. for her because the arrest actually forced her to get off painkillers and forced her into counseling and that she was finally able to get the help that she needed and that it quite possibly

ended up saving her life. So good for her.