Winona Ryder: Drowning, Designer Theft, and a Deadly Kidnapping

Summary

DISGRACELAND Episode Summary: "Winona Ryder: Drowning, Designer Theft, and a Deadly Kidnapping"

Episode Details:

• Title: Winona Ryder: Drowning, Designer Theft, and a Deadly Kidnapping
• Host/Author: Double Elvis Productions
• Release Date: April 29, 2025

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1. Introduction

In this gripping episode of DISGRACELAND, host Jake Brennan delves deep into the tumultuous life of actress Winona Ryder. From a harrowing near-drowning experience in her youth to high-profile scandals and her complex involvement in a notorious kidnapping case, Ryder's story is a compelling mix of tragedy, fame, and personal struggle.

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2. Winona Ryder's Early Life and Near Drowning Incident

The episode opens with a vivid recounting of Ryder's childhood trauma:

Guest Speaker (03:22): "Winona Ryder is named after her town in Minnesota, for fuck's sake. No one was quite like her."

At 12 years old, Ryder nearly lost her life to a drowning incident, an event that profoundly impacted her psyche. The narrative paints a chilling picture of the 1980s setting, emphasizing the lack of modern technology which made such a tragedy even more terrifying:

Narration (04:48): "Winona had seconds to determine whether she was going to live or die. The seconds ticked by slowly and the undertow moved quickly."

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3. The Polly Klaas Kidnapping Case

The episode shifts focus to the Polly Klaas case, a high-profile kidnapping that shook California:

Jake Brennan (05:20): "Kidnapping case that would rattle California and Winona Ryder to her core."

Ryder's unique upbringing, influenced by her godfather Timothy Leary, an LSD pioneer, instilled in her a relentless questioning of reality and fear of the unknown. This fear was exacerbated by the Polly Klaas disappearance, where Ryder played a crucial role:

Guest Speaker (03:35): "Her godfather was LSD pioneer Timothy Leary, AKA the Most Dangerous man in America."

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4. Winona's Involvement and Aftermath

Ryder's personal experience with fear and trauma intertwined with her involvement in the Polly Klaas case. Her celebrity status brought national attention to the missing girl, leading her to offer a substantial reward for Polly's safe return:

Guest Speaker (04:04): "Winona Ryder offered $200,000 to any person who could safely return Polly to her parents."

Despite her efforts, Polly was tragically found deceased, a revelation that devastated Ryder and left lasting scars:

Narration (17:07): "Polly's family had prayed their search would end soon. They just didn't imagine it ending like this."

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5. The Shoplifting Incident and Trial

In a shocking turn of events, Ryder became embroiled in a shoplifting scandal, stealing over $5,000 worth of designer clothes. The episode details the elaborate theft, including:

Narration (05:30): "Winona snuck her contraband into a Saks Fifth Avenue shopping bag. The same bag from earlier that afternoon..."

Ryder's subsequent trial became a media spectacle. Despite her charitable work and involvement in the Polly Klaas case, the prosecution remained unsympathetic, leading to Ryder receiving 480 hours of community service and significant fines, but avoiding prison time:

Narration (27:14): "The judge emphasized that if her sticky fingers ever stole again, she'd undoubtedly be pouting behind bars next time."

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6. Career Changes and Comeback

Following her legal troubles, Ryder took a deliberate step back from acting to avoid burnout and reassess her career. She transitioned to supporting roles and diversifying her portfolio, appearing in critically acclaimed films such as "Black Swan" and collaborating with renowned directors like Darren Aronofsky and JJ Abrams.

The episode highlights her resurgence with Netflix, where she embraced roles more fitting to her matured persona, notably portraying a suburban mother in the hit series "Stranger Things":

Narration (43:20): "And that is anything but a disgrace. I'm Jake Brennan and this is Disgraceland."

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7. Conclusion

The episode beautifully ties Ryder's personal struggles with her professional journey, illustrating how trauma and resilience shaped her path. From narrowly escaping death as a child to navigating the treacherous waters of Hollywood scandals, Winona Ryder's story is a testament to the complexities of fame and personal growth.

Key Takeaways:

• Early Trauma: Ryder's near-drowning experience at 12 years old.
• Kidnapping Case: Her pivotal role in the Polly Klaas disappearance.
• Legal Troubles: The high-profile shoplifting incident and its repercussions.
• Career Resilience: Ryder's strategic career moves leading to a successful comeback.

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Notable Quotes with Timestamps

• Guest Speaker (03:22): "The stories about Winona Ryder are insane. She nearly drowned when she was just 12 years old. She once stole more than $5,000 worth of designer clothes on a whim..."

• Jake Brennan (05:20): "Kidnapping case that would rattle California and Winona Ryder to her core."

• Narration (04:48): "Winona had seconds to determine whether she was going to live or die. The seconds ticked by slowly and the undertow moved quickly."

• Guest Speaker (03:35): "Her godfather was LSD pioneer Timothy Leary, AKA the Most Dangerous man in America."

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Final Thoughts

This episode of DISGRACELAND masterfully intertwines true crime with the dark underbelly of Hollywood, presenting a nuanced portrayal of Winona Ryder's life. It's an enthralling listen for those fascinated by the intersections of fame, tragedy, and personal redemption.

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Note: To experience more such intense and captivating stories, consider subscribing to DISGRACELAND and exploring their vast library of true crime tales from the entertainment industry's shadowed corners.

Transcript

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Disgraceland this episode contains content that may be disturbing to some listeners. Please check the show notes for more information. Disgraceland is a production of Double Elvis.

[Guest Speaker]

The stories about Winona Ryder are insane. She nearly drowned when she was just 12 years old. She once stole more than $5,000 worth of designer clothes on a whim, even.

[Jake Brennan]

Though she was a super famous and.

[Guest Speaker]

Successful actress at the time. Earlier, she was raised by beatniks off the grid in Northern California. Her godfather was LSD pioneer Timothy Leary, AKA the Most Dangerous man in America. Winona's unique upbringing molded her into an A list actress and into America's endearing weirdo. Her weirdness drew from the deep fears that she experienced when assimilating from a sheltered early childhood to a more typical 1980s media overload when her family moved to California. And when one of those fears came true in her new California hometown, she found herself in an unlikely role, trying to draw attention to a horrific crime to help solve a kidnapping case. Before and after her involvement in that case, Winona Ryder made great films. And Winona Ryder made time with some.

[Jake Brennan]

Great musicians as well.

[Guest Speaker]

Musicians who, well, you know what I'm going to say. Musicians who made great music.

[Jake Brennan]

Unlike that music I played for you at the top of the show.

[Guest Speaker]

That wasn't great music. That was a preset loop from my melotron called Johnny Forever MK1.

[Co-host]

I played you that loop because I.

[Guest Speaker]

Can'T afford the rights to Dream Lover by Mariah Carey. And why would I play you that specific slice of five octave cheese? Could I afford it? Because that was the number one song in America on October 1, 1993. And that was the day Polly Klaas was abducted from her home, opening a.

[Jake Brennan]

Kidnapping case that would rattle California and Winona Ryder to her core. On this episode, near drowning, designer theft.

[Guest Speaker]

A deadly kidnapping, and America's alt sweetheart.

[Jake Brennan]

Winona Ryder? I'm Jake Brennan and this is Winona Ryder had seconds to determine whether she was going to live or die. The seconds ticked by slowly and the undertow moved quickly. A current whipped Winona's body around like a rag doll. It yanked her in circles, shook her like a snow globe. And the ocean closed in on her from every angle. It dragged her farther into the deep. 5ft below, 10ft below. Winona wasn't sure, but she knew she was fully submerged. Down was up, left was right. She spun until she had no clue which direction would lead her to safety. This was not a riptide. Winona Ryder could not calmly bob at the surface of the water and flag down help. Someone who could pull her back up to shore. She was caught in the undertow and the incoming waves bent Winona to their will. Winona thrashed her arms and legs. She was motivated entirely by desperation. She struggled to wriggle free from the ocean's grass. And the more she jerked her body around, the harder it was to focus. Keeping her mouth clamped shut, she held out as long as she could. She clung to one thought. Don't breathe. Don't breathe. And the sudden yank of the undertow pried open her lips anyways. A silent scream. A stream of air bubbles from her mouth. More than she ever knew she had in her. Her air supply was racing towards the surface and there was only water now. A surge of seawater gushed into her mouth. The salt seared her windpipe as it forced its way into her lungs. Winona couldn't stop the flow. It burrowed into her chest, deeper and deeper until it felt like her lungs would pop. She choked as her body tried to cough, tried to puke, tried to do anything that would stop her from sinking to the ocean floor. Pruning and ragged, lungs ready to rupture. Winona's limbs slipped away. She lost all feeling in her arms and legs. She surrendered to the ocean. She surrendered to the ability to feel much of anything at all. Her peripheral vision darkened. Black curtains shrouded her sight. Her view narrowed to a fine tunnel thousand yards long. And she stared down the corridor. Empty, quiet. Numb. She didn't feel it when a lifeguard hoisted her from the water and laid her down on the sandy beach. Her body was limp, her skin a ghastly shade of porcelain. She had no pulse. 12 year old Winona Ryder was dead. The lifeguard started to perform cpr. Even though she looked like a lost cause, it was what he was trained to do. He pushed down on her chest, over and over. He tilted her head back, pinched her nose tight with his fingers, put his mouth on her blood blue lips and tried to breathe life back into her. Suddenly she twitched to life. She shot salt water into the sand by the mouthful. Winona's friends watched from the sidelines, stupefied or too stoned to understand the severity of what had just happened, what almost happened, and their glazed eyes watched the vomit bring a blush of color back to Winona's cheeks. And then a thought dangled in the back of their dazed minds. Our parents are going to fucking kill us. This was the mid-1980s. There were no smartphones. There was no Internet. It was easy for preteens to go missing for a few hours. In fact, it was expected. Legions of suburban latchkey kids went to school, came home if they felt like it, fucked off down to the river or into the woods or even to the beach and just be home by dinner. Looking back at the 80s from the 2022 point of view, it might seem like this connection was standard operating procedure. And it kind of was. You might not even notice that the kids were missing until the street lights came on. That's what Winona Ryder and her friends were counting on when they cut class earlier that day. The group left the drama of junior high in their lockers and rolled up to Dillon beach instead, where they rolled a skinny joint and sunned their stone cells on the shore. Young Winona declined the drugs. She embraced the ocean instead, right until the undertow hugged her back so tightly that it almost didn't let her go. Winona survived that day barely. The cold clench of death lingered in her bones. Later that evening. She felt it prying at her skin, pulling her under. Fresh dose of fear followed her home to Petaluma. Trailed her like a shadow. Climbed into bed with her, laid by her side like an old friend, right next to all our other old childhood fears. The tally in her head was impressive. There was the Holocaust for one, the horrors of Nazi Germany that claimed so many of our ancestors. No one could convince Winona those ghosts weren't real. There was also the ever present fear of nuclear annihilation, but that was nothing that out of the ordinary for all kids in the 1980s. Then there were the neighbors. She wanted to get inside their heads, know what they thought when her parents hippie van pulled into the driveway every day. What they thought of this new family, some implants plucked from a progressive commune in Northern California. Well, commune wasn't even the right word, but that's what Everyone kept calling it Commune. Sounded like a cult. And there was no cult where Winona came from. That was a flat out misconception. Other details were correct, though it was true that her last home had no electricity, no phone, no tv. Winona's hippie parents replaced technology with free thinking. Traded the paranoia of broadcast news with nature. It was idyllic. Idyllic until you tried to explain it to anyone else. Winona worried the neighbors would misunderstand their family, conspire against them. She wondered if they would connect the dots that her godfather was the most dangerous man in America. Well, according to Richard Nixon anyway. Winona's parents appointed psychologist and LSD advocate Timothy Leary as her godfather. The guru of turning on, tuning in and dropping out. He told Winona to question everything. So she did. Just like she was in bed right now. Wide eyed, staring at the ceiling, driving herself right up the wall, questioning. Sleep frequently escaped her. Winona didn't know the word insomnia yet. What if the neighbors turned on us? She thought. What if they tried to lock us away? There was another question burning a hole in Winona's restless mind. Why do children keep disappearing in California? That was the one fear that dwarfed all the others. The one that tortured her every time she indulged in the new luxury of watching television. Winona Ryder's worst fear was getting kidnapped. Gone were the days of living in a secluded bubble, cozy amongst the company of her parents and their fellow free thinking friends. Now that Winona lived in Petaluma, California, she heard everything. There was no shelter from reality. Not with a TV in the house beckoning to her at all hours. Kidnappings colored the screen on a regular basis. Some cases went in circles for months until they reached a tragic dead end. Emphasis on dead. Others never ended at all. Winona knew some of the victims names by heart. Tara Burke, 3 years old. Held in captivity for 10 months by sexual predators. Steven Stayner, 7 years old. Trapped for 7 years by a child molester. He only escaped because the sick bastard who abducted him wanted to lure in another boy. And the two kids made a mad dash together. Then there was Kevin Collins, 10 years old. He was from the same neighborhood as Winona. Her older sister even babysat her once. His bucktooth smile was printed across billboards and national magazine covers. A literal milk carton kit. He was still out there somewhere. Dead or alive. Nobody knew. No one might ever know. The chill of fear borrowed deeper into Winona's bones. She pulled the covers over her head. Her fingers trembled. But no one could convince her she was overreacting, that her fears were unrealistic or childish. She almost died today. Anything could happen to anyone without rhyme or reason, and that might be the part that scared her the most.

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His blood ran cold when he saw the red and blue flicker against the trees. The colors were getting brighter and deeper. He knew the cops would show up eventually. It wasn't a matter of if it was a matter of what when. Deep breaths. He coached himself. He casually leaned against the hood of his car as the cruiser pulled over. He paced his breathing. He practiced his story in his head. But Richard Davis still didn't feel prepared. Sightseeing. He was just sightseeing, that's all. Pulled over to admire the great outdoors on a warm evening. Then he realized the sedan was stuck in a ditch. Wrestled with the damn car for hours. Even crawled underneath at one point. Been here ever since. Yeah, that would work. Davis recited the story word for word when a pair of police officers approached him. Their version of the story was slightly different. They had received a call about a mysterious man camped out on the side of the road on private property. It was all over the police scanner that night. Channel 3, to be precise. Channel 3 covered all of Sonoma Valley, San Pablo Bay, to Santa Rosa. But it did not extend to petaluma, a city 17 miles away. In Petaluma, the scanner had different intel. In Petaluma, a 12 year old girl had been kidnapped by a stranger. The very same girl Richard Davis just dumped in the woods. Little Polly class left a window open on October 1, 1993. Or maybe her mother left it ajar right before passing out on a sleeping pillow to escape a tedious migraine. Didn't matter. It was too late now. The window offered an invitation, and Richard Davis accepted it. He made quick, clean work. He slithered right through the open window and into the house. Picked up a knife in the kitchen. He cut the cords from video game controllers. Ripped up some bed sheets, too. He'd need binding materials for this to go smoothly, and the strips of cloth didn't have to be big. Children had itty bitty wrists and ankles. Davis barged into Polly's bedroom as the family clock chimed. 10:30pm May as well be midnight to a 12 year old. Or so Davis thought. He wasn't expecting to find Polly's slumber party just heating up. Davis saw panic flood the eyes of every girl in the room. He lingered in the doorway. The edge of the knife glimmered against the glow of Polly's clamshell nightlight. Davis kept his instructions simple. Scream and I'll slit your throats. They obeyed, shaking in silence. Davis then bound and gagged each girl, tied them up with their own sheets and video game cables, and then he bagged their heads with pillowcases from Paulie's bed. He blinded all the girls except Paulie. He had other plans for her. Davis bent down on his knees, eye level with the trembling hoods count to 1,000, he ordered. Paulie will be back by then. Paulie would not be back. Paulie was tied up in the woods in Santa Rosa, California, and the local police force had no idea. All because they were tuned to the wrong channel on the police scanner. Channel three. One cop used a flashlight to look Davis up and down. Leaves and twigs poked out of his shaggy haircut, beads of sweat on his cheeks. His body language betrayed him. Davis just looked nervous. Not car trouble nervous like when you're stranded at midnight with a flat. The guilty kind of nervous. One hand in the cookie jar nervous. But looking nervous wasn't against the law. And the other cop returned to the cruiser. He pulled up a report that summarized Richard Davis driving record. Technology failed the police a second time that night. And the cursory report didn't include anything about Davis's criminal history, which would have revealed that he was a convicted felon. In fact, he was recently paroled after an eight year prison sentence for kidnapping. But with their limited 1993 technology, all of that went uncovered. The police found no dirt on Richard Davis beyond the dirt that covered his hair and clothes, which he claimed was a result of trying to free his car from the ditch. After a tow truck dragged David Davis car back to the road, the police escorted him to the highway. He killed time in the fast lane for 20 minutes before he circled back to retrieve his stolen treasure. Davis parked properly this time and he ducked back into the woods to find Polly class. He dodged branches and knotted tree roots by the light of the moon and found Paulie where he left her a few hours earlier. He slung her over his shoulder. He untensed his muscles and release the nervous energy that had been racking his body since the police arrived. But Petaluma's panic was only just beginning. There was a long standing rule when it came to child kidnappings. The chances of finding an abducted child alive or at all shrank significantly after the first 48 hours. The petaluma police department had to act quickly. Paulie's life could depend on it. And the FBI joined the case overnight. Bloodhounds, helicopters, detectives rang up scores of ex cons. They interviewed sex offenders in surrounding counties. Alibis checked out. Every volunteer and investigator came back empty handed. Except for one thing. The perpetrator left behind a palm print pressed into Paulie's bed frame. The FBI's database didn't include palm prints in 1993. This was unmapped territory. But it was literally all they had. And the clock kept ticking. The case spread like A California Wildfire. Banners decorated the haunted town right down Petaluma Boulevard. Let Paulie go. The signs cried, scribbled in sloppy handwriting of school children. Paulie's image covered public buildings. Her face cried out from flyers scattered across parks, libraries, shopping malls. Her story never left the news. An information hotline was a regular fixture on TV screens, and viewers were implored to call. Over the course of the case, that hotline received more than 12,000 calls. That's 12,000 leads. All dead ends. The hotline rang again late in the night, about 10 days after Polly disappeared. A volunteer picked up the receiver. Soft sobs echoed on the other end of the line. The caller was moved to tears. She claimed she once lived only two neighborhoods away from Polly's house and that they even went to the same junior high school. She just saw the news as she was calling from the lobby of a Los Angeles hotel and the volunteer asked for her name. Winona. She didn't have to say her last name. The volunteer could tell who it was from her voice alone. The sulky, unaffected teen in Beetlejuice, the love interest of Johnny Depp in Edward Scissorhands. And in in real life, for that matter, the girl who literally killed her classmate on screen is part of a cruel series of fake suicides in the dark comedy Heathers. But this call wasn't an act. Winona Ryder's sorrow spoke volumes. Her tears practically trickled through the phone. Winona couldn't believe such a tragedy had struck Petaluma. Polly's parents couldn't believe someone as notable as Winona Ryder wanted to pitch in. There was perhaps no greater force that could pull Polly back to them. Polly was a Winona superfan. One of her greatest wishes was to meet her in person. Then again, most tweens, teens and fully grown adults felt the same. In 1993, Winona Ryder was the 90s. She was cool as shit. Her head to toe black ensembles were of goth light legend. Her eyes were brooded with attitude. Her smile could slice your heart open. She was on par with the other brilliant movie beauties of the day. Sure, Julia Roberts, Uma Thurman, Nicole Kidman. But Winona was different. She was weird, wicked, wonderful, all wrapped into one peculiar package. She was named after her town in Minnesota, for fuck's sake. No one was quite like her. Winona's assistance with the polyclass case was wavered between low key and high profile. She could answer the information hotline and join in person searches just the same as any ordinary volunteer. Yet her celebrity status meant Everyone listened when she spoke. Tabloids, fans, film critics. Winona witnessed the world's unquenchable thirst for a look into her private life. Then she yielded it to her advantage. If Winona accepted interviews, she automatically drew more national attention to Paulie's disappearance. Certain news outlets had no interest in reports about Polly without their precious Q and A's for Winona. First, Winona forced America to pay attention to the case. Then she put a price on it. Winona Ryder offered $200,000 to any person who could safely return Polly to her parents. Weeks dragged on months. Polly's parents published a letter to the kidnapper in the San Francisco Chronicle, imploring the stranger to bring their girl home. They left a note for Polly, too. Our darling, if you can read this, please know that your mommy and daddy love you so much, and we will continue to search for you until we can hold you safely in her loving arms again. Every time Winona returned home from volunteering, she peeled the optimistic smile from her face. She would lay in bed and let the insomnia knock around all the bad thoughts in her brain again. The hope never left Winona, but it waned. Her childhood fear of kidnapping gnawed at it. Winona almost died when she was 12 years old, too, and this could have been her. Anything can happen to anybody. You could become a mega movie star, or sink like a stone to a watery grave at the bottom of the ocean, or vanish from your bedroom, never to be seen again. Winona rolled over and turned her back on the fear. But it waited behind her and alongside her in bed, just like it had 10 years ago. We'll be right back after this world.

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[Jake Brennan]

The police did find Polly Class, but they didn't find her alive A cool breeze whipped across an abandoned mill yard, an overlooked eyesore in Cloverdale, California, right off Highway 101, 30 miles from Petaluma. Richard Davis trudged through the empty field. Dry grass crunched under his boots. The police followed close behind him. He was taking them directly to Paulie. This time, Davis wasn't hiding anymore. He couldn't. The secrets he stashed in the woods were out in the open now. Davis was sloppier than he realized on that night two months months ago. The police made him panic on the night of the kidnapping, and his heart pounded. The sound drowned out his careful calculations. His attention to detail slipped away. Kidnapping tools slipped out of his grasp and left a trail of evidence in the forest. A piece of silk fashioned into a hood. Strips of packing tape perfect for binding. A pair of girls tights tied into a knot, complete with a tangle of human hair. A resident of Santa Rosa uncovered the clues when loggers cleared a portion of the woods on her property in December of 1993. She was familiar with the class case. By now most of California was after hearing about Paulie's disappearance for weeks on end. And now it was her turn to dial the information hotline. But there was something else. The jarring discovery in the world woods jogged the woman's memory. There was a man stranded on her property not too long ago, sweaty, panic stricken, roughly two months prior, right around the same time Paulie went missing. When the police came to retrieve the items from the woods, she reminded them about the trespasser. They summoned the Santa Rosa police records for good measure on Oct. 1, police called the tow truck for a man named Richard Davis. And they knew that much to be true. But back at the station, there was more information about this man than just a flimsy printout of his driving record. Davis was an ex con. His criminal record never seemed to end. Burglary, assault with a deadly weapon, assault with intent to rape, auto theft, kidnapping. Kidnapping. Richard Davis did eight years in prison for kidnapping. He was paroled in June of 1993 after serving only half of a 16 year sentence. Three months before Polly went missing on October 1, police had their prime suspect in the kidnapping of Polly Klaas right there standing in front of them. And then they escorted him to his escape route. Investigators pored over his criminal record. Police even wrangled Davis a second time later in October. Arrested for drunk driving, Davis then violated his parole by failing to appear in court. A warrant was out for his arrest. Bingo. Police had their in. They weren't letting Richard Davis slip away a third time. They found him cruising around town in a van not far from where he was staying on the Coyote Valley Indian reservation, about 75 miles north of Petaluma. Police booked him on violation of his probation, cuffed him, tossed him in the clink. And then they took his palm print. It was an exact match for the print found on Paulie's bed frame. Investigators shared a knowing glance. The search for Paulie's kidnapper was over. Davis knew it was over, too. He cracked after a few days. I screwed up big time, he told the police. And now Davis was retracing his steps with the police by his side. He paused at a collection of weathered lumber. Mushrooms sprouted from the heat. He thrust his chin towards the rotting pile. Investigators overturned the pile, board by board. They found Paulie resting underneath, haphazardly tucked into a shallow grave. Polly's family had prayed their search would end soon. They just didn't imagine it ending like this. And the closure shattered the class family, now one member too small. It shattered Winona Ryder, too. Her heart shriveled up and shrank. It reverted back to being 12 years old, beating at a ragged pace like she was a preteen, tortured by the undertow, once again barely clinging to life. Maybe Polly once felt the same when she was tied up in Davis's sedan. Winona would never know. She would never get the chance to facilitate Polly's happy ending. Winona struggled through the premiere of her new film, reality bites, in February 1994. The irony of the title sunk its teeth into Winona's soul. She successfully convinced Universal Pictures to make the Los Angeles debut of the movie, a benefit for the Poly Klaas Foundation. But her work still felt unfinished, woefully inadequate. Polly's greatest wish had been to meet Winona in real life, and that couldn't happen now. So Winona did the next best thing. She reached for Polly through fiction. Winona accepted the role of Jo March in a new movie adaptation of Little Women. It was Polly's favorite book. Winona brought the story to life and dedicated her performance to Polly's memory. The role was a breath of fresh air for Winona. For once, she wasn't the weirdo. She wasn't bewitching. She was the strong female lead, determined and dependable, just like she had been for Polly's family. For two months. Winona used Little Women to shoo away the darkness crowding her life, the same shadows that housed her fears and lingered by her side when she couldn't get any shut eye. Life didn't have to be a big, dark room all the time. Maybe through her performance in Little Women, directors and casting agents would see that, too. And if they didn't, Winona had to escape on her own before that big, dark room caved in on her completely. She would have added it all up if she could think clearly. Winona Ryder's hands made quick work on the floor of a Beverly Hills fitting room. A Marc Jacobs cashmere sweater, $760. These Saint Laurent blouse, another 754 handbags. Those were at least two grand. A handful of expensive hair bows and bands worth about $600, and six pairs of of socks just for good measure. And those were 80 bucks. With a snip of each security tag, Winona snuck her contraband into a Saks Fifth Avenue shopping bag. The same bag from earlier that afternoon, her first shopping spree already gave her credit card a $3,000 workout. But if all went as planned, the second round was going to be on the house. Winona crinkled a handful of tissue paper in the bag to cover the sound of her sniffs. When space ran out in the Saks bag, she stuffed the stolen clothes into bags she brought from home. A shopping assistant knocked on the door. Winona froze in her position, bent over on her hands and knees, scissors in one hand and a pair of cashmere Donna Karan socks in the other. The clerk asked if the A List client needed anything. A Coke, winona said. A Coke from the Saks Fifth Avenue cafeteria. Apparently shoplifting made her thirsty. The assistant's designer heels clicked on the tile floor towards the cafeteria. Fuck, she used that distraction once already, didn't she? Winona rubbed her forehead. Now where was she? Right, the bags. Fill the bags, blend in, then bust out of there. Winona loaded the bags onto her arms. She walked towards the exit with confident strides. Her gait spoke for her. Why yes, of course I already bought all this. I'm a celebrity. Why would I shoplift? Security didn't buy her charade. Instead, they wanted to know when she planned on buying the designer goods visibly stashed in her armful of bags. First she played dumb, insisted her assistant had already paid for the clothes. Then she switched stories and claimed the employees were keeping track of her massive haul and would just add the items to her first bill. As if designer department stores let you keep an open tab like a By the time the police arrived, Winona confessed to the crime. Using a uniquely Hollywood excuse. She explained that a director instructed her to shoplift as research for her upcoming role in a movie called Shop Girl. Or was it called White Jazz? Winona's web of incoherent tales impressed no one. She left the Beverly Hills department store in handcuffs on December 12, 2001. They wanted strange and unusual. She would show him strange and unusual. It was a new century now. A new millennium even. But pop culture still wanted the winona of the 90s. A dark haired goth girlfriend to tantalize them in Tim Burton films. A cute, cuckoo like girl interrupted her most recent Smash hit from 1999. Winona's heart thudded with fear as she ducked into the back of a cruiser. Yet a snicker spread across cross her lips. She could be a felon now. She was still the outcast. Still the weirdo. Typical. One year later, Winona Ryder was not snickering. She was sweating. Her dark eyes darted across the courtroom from one stone faced lawyer to another. She understood about half this legal jargon they were spouting off. But she knew two things to be true. One, she was already guilty. She was a felon. It was right there in the shoplifting charges. Felony grand theft. There would be repercussions. Two, one of those repercussions could be jail time. Apparently her lawyer's 100% real defense that Winona was too fashionable to shoplift and carry any weight in a Beverly Hills courtroom. Winona uncrossed her legs for the seventh time that day. Fidgeting didn't speed the sentencing up. This was one story she couldn't flip to the end of the script and spoil the ending. She had to sit through a bunch of men in suits bickering over her character? Not a character. Her character. Not just another dark haired beauty throwing smoldering glances across haunted mansions at movie sets. The people gathered in that courtroom had to see Winona. For Winona, her actions, not her acting, would determine her future, which may or may not involve trading her pile of stolen designer booty for an orange jumpsuit. Winona's defense brought forward her extensive involvement in the poly class kidnapping as the clearest example of her sterling character. Sure, she had donated a fat stack of cash to the polyclass foundation, but she rolled up her sleeves alongside other regular volunteers, too. It was a tender, egoless gesture that Winona repeated for weeks. Maybe her help hadn't brought Polly back, but her murderer, Richard Allen Davis, was on death row and that was the second best case scenario. The prosecution refused to soften. Instead, they snapped. What's offensive to me is to trot out the body of a dead child, the opposing lawyer retorted. Winona sprang up from the bench, her eyes welled with tears. Her lawyer objected before she could defend her involvement and before she could explain why that case still rattled her to this day. How seeing her worst fear, the fear of being kidnapped, come to life in a little girl not unlike herself, shattered her heart. Maybe no one really knew Winona at all. She plopped back into her seat with a sigh. Winona sighed again when the judge announced her penance. 480 hours of community service and nearly $10,000 in fines and restitution. No prison sentence. The judge emphasized that if her sticky fingers ever stole again, she'd undoubtedly be pouting behind bars next time. The happy ending to her trial also created a happy ending for Winona's winning streak at the box office. For most actresses, an acting hiatus would be devastating. For Winona, it was a relief. She actually called her arrest the best thing that could have happened in court that day. December 6, 2002 Winona was 31. She started acting in films when she was barely 16, and she never stopped. Winona Ryder performed more than 20 movies in the span of 15 years. A break was long overdue. After her sentencing, she veered away from her strict regimen of back to back leading roles, took a step away from movie sets and set new boundaries for herself, ones that would keep acting burnout at bay. She broke her newfound bliss sporadically for her special roles, a hilarious turn as Commandment Breaking Puppet loving Kelly LaFonda and David Wayne's The10 in 2007, JJ Abrams Star Trek reboot in 2009 Tim Burton's claymation creation Frankenweenie Darren Aronofsky's noir thriller Black Swan, which involved Winona repeatedly plunging a steel nibble nail file into her cheeks. But another script came across her desk years later that contained the real comeback gold. Something happened to Winona when she took that break. Something inevitable. She aged. By the 2010s she was in her 40s. Casting agents couldn't picture her as a 20 something love interest in movies anymore. That's when Netflix called. They gave her a shot at a role that would be more age appropriate. A mother. Your average suburban mom in the early 80s. Totally normal, a little nervous perhaps. But with the stranger Danger panic at the time, what parent wasn't? They needed her to portray a woman who would be tested. A woman who could portray gut wrenching fear and grief in her eyes without uttering a word. A woman whose son would vanish without a trace. It's an uncanny coincidence, but stranger things have happened. And that is anything but a disgrace. I'm Jake Brennan and this is Disgraceland.

[Co-host]

All right, thanks for riding on this Winona train with me here through Disgraceland Apple Podcast listeners, make sure you have auto downloads turned on. And guys, this week's Question of the.

[Jake Brennan]

Week which actress most embodies Gen X for you? And why is it Winona?

[Guest Speaker]

Drew Cameron?

[Co-host]

Penelope? Let me know 617-906-6638 with your answers via voicemail and text and Disgracelandpod on the socials and I'll answer you back in the next afterparty bonus episode in your podcast feed. Leave a review for Disgraceland on Apple Podcasts or Spotify and win some free merch. Alright, here comes some credits. Disgraceland was created by yours truly and is produced in partnership with Double Elvis.

[Jake Brennan]

Credits for this episode can be found.

[Co-host]

On the show notes [e-mail] if you're listening as a Disgraceland All Access member, thank you for supporting the show. We really appreciate it. And if not, you can become a member right now by going to Disgracelandpod.com.

[Jake Brennan]

Membership members can listen to every single.

[Co-host]

Episode of Disgraceland ad free. Plus you'll get one brand new exclusive episode every month, weekly unscripted bonus episodes, special audio collections and early access to merchandise and events. Visit disgracelandpod.com membership for details, rate and review the show and follow us on Instagram, Tick Tock, Twitter and Facebook @DisgraceLandPod and on [e-mail] DisgraceLandPod pod Rocka Rolla.

[Jake Brennan]

He's a bad, bad man.

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