Highlights

  • Winona Ryder's 2000s career was damaged by projects like Friends cameo being called a "lame stunt."
  • Despite scandal, 2001 theft conviction, Ryder's comeback in Hollywood started with Black Swan in 2010.
  • Issue of double standards in Hollywood, ageism, and lack of roles for female stars affected Ryder in 2000s.

Winona Ryder ruled in the 1990s in movies like Girl, Interrupted where she had a difficult time with Angelina Jolie; The Age of Innocence alongside intense method actor, Daniel Day-Lewis; and Edward Scissorhands where Ryder fell in love with her ex-fiancé, Johnny Depp. So it only made sense when she made a cameo on Friends in April 2001. Unfortunately, it was called a "lame stunt."

It was a terrible year for the actress who was convicted of grand theft and vandalism in December. But the scandal wasn't the only reason her Hollywood career tanked. As it turned out, projects like her Friends appearance did more harm than good for her 21st-century act. Here's a closer look at Ryder's life in the 2000s.

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Winona Ryder's 'Friends' Lesbian Kiss With Jennifer Aniston Was A "Lame Stunt"

On April 27, 2001, Entertainment Weekly released a review of Ryder's Friends cameo called, "Why Friends lesbian kiss was a lame stunt." The subtitle read, "Guest star Winona Ryder deserved better -- and so do fans, says Nicholas Fonseca (writer of the piece)." In the episode, Jennifer Aniston's character Rachel Green reunites with her sorority sister, Melissa (Ryder), with a college friend whom she kissed during a fraternity party.

Rachel then kissed Melissa again to remind her of their fling. Fonseca called it the "worse" part of it all. He wrote: "What's worse, the kiss — which occurred in the present, not a flashback, because Melissa couldn't remember it at all — immediately sparked old feelings of passion in Ryder's character, a lesbian, who apparently carried a torch for Rachel for years. (Yeah, right. Like any self-respecting lesbian would wear a powder blue power suit.)" But he also "digressed," saying:

" Friends has never been a gay show, so its depictions of homosexuality — or same sex kissing experiments — probably shouldn't be the subject of any doctoral theses."

While Fonseca thought Ryder deserved better, he acknowledged that the Friends "episode offered a glimmer of hope for Ryder, a two time Oscar nominee who hasn't exactly been blessed at the box office in the past few years." But he advised her: "Find a good comedic script, girl, and soon you won't have to resort to unnecessary NBC sitcom guest spots to win back our respect." The Mermaids star received Oscar nominations for her performances in The Age of Innocence (Best Supporting Actress) and Little Women (Best Actress).

Winona Ryder received a star on the Hollywood Walk of Fame in 2000.

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Winona Ryder Was "Robbing Everything In Sight" Months After Her 'Friends' Cameo

In December 2001, Ryder was convicted of grand theft and vandalism after shoplifting over $5,000 worth of products from a Beverly Hills store. She was then sentenced to probation and community service. In addition to that, she had to pay a $3,700 fine and $6,355 in restitution to the store. At that time, she denied the crime, saying she was only doing research for a kleptomaniac role.

Her first post-scandal gig came in 2003. She landed a small role in Vincent Gallo's independent film, Brown Bunny. "I knew she was going to jail, and this will be good for the movie… I would never cast Winona Ryder in a significant role," the director said of the casting choice.

"She was not in great shape at the time, and she was robbing everything in sight," Gallo continued.

He ended up firing Ryder after catching her stealing on the sets. Since then, the Heathers star was practically blacklisted from Hollywood. But in 2016, she explained to Porter magazine that she didn't "just [disappear] in the 2000s." She confessed: "Psychologically, I must have been at a place where I just wanted to stop. I won't get into what happened, but it wasn’t what people think. And it wasn't like the crime of the century!"

She went on to share that the hiatus helped her refocus. "But it allowed me time that I really needed, where I went back to San Francisco and got back into things that... I just had other interests, frankly," she added. "A lot of people had the perception that I just disappeared in the 2000s. And I did, but only from that world [of acting]. I appeared elsewhere, I promise you. I was transformed into doing stuff I really wanted to do – it was a great awakening. It just wasn’t in the public eye."

Here's a timeline of Ryder's Hollywood comeback following her 2001 scandal:

2001

Grand theft and vandalism conviction

2003

Ryder was caught stealing on the set of Brown Bunny

2004

Start of her acting hiatus

2010

She made her mainstream movie comeback in Black Swan as a troubled, ousted prima ballerina

2016

She was cast in Netflix's Stranger Things as Joyce Byers

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Winona Ryder's Shoplifting Wasn't The Only Reason She Vanished From Hollywood

Many people think Ryder was simply canceled following her 2001 conviction. But in a 2018 article by Forbes, they cited other "grim reasons" such as "the double-standard of how men and women are treated in Hollywood," per former staff writer Scott Mendelson. "By the time Ryder returned, she had 'aged out' as a potential love interest," he wrote. "She turned 35 in 2006. Even Anne Hathaway admitted three years ago to losing out on parts (at 32) to 'new' 24-year-old starlets."

"...Who is to say it wouldn't have been the same even absent [Ryder's] criminal transgression?"

Mendelson argued that it "would be less of a problem if Hollywood made starring vehicles for actresses even somewhat on par with the number offered to actors. But that is not remotely true today, and it was even less accurate in the mid-2000s." He also noted that "by the time Ryder came back, Hollywood had stopped making or releasing movies like How to Make an American Quilt, Reality Bites and Girl Interrupted."

The writer continued: "It's a problem that crushed an entire generation of (to be fair, mostly white) actresses and was part of what led a whole generation to flock to television for meaty roles."

In 2002, Winona Ryder said the Hollywood "business is brutal" where "leading men were routinely cast with love interests two decades younger."

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