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A Look Back at Winona Ryder’s Best Fashion Moments in Film

Winona Ryder recently worked on a film, Frankenweenie, with Beetlejuice director and Edward Scissorhands director/producer Tim Burton. This, along with news of Bravo’s forthcoming Heathers small screen reboot, means buzz has been mounting around the forty-year-old actress. There’ve even been talks of a Beetlejuice sequel.

Ryder, whose most notable recent film role was as a crazy person in Black Swan, has never not looked incredible in a movie. We’re pretty sure it would be impossible to make her look bad, as she’s proven time and time again that there’s not a time period, sanity level, or hairdo she can’t pull off.

Or maybe she’s just been fortunate enough to portray some seriously stylish people. From Heathers to Reality Bites to Lucas, click through for Winona Ryder’s best fashion moments in film.

To view the slideshow, go to Fashionista.com website

Freed Winona: Ryder On Her Troubled Past, ‘Iceman’ Present and Ruth Gordon Future

“I’ve loved making movies,” Winona Ryder said in Toronto earlier this week when reflecting back on her 26-year career. “I feel like I’ve been so lucky because I’ve gotten to be in movies that are some of my favorites, regardless of my being in them — like ‘Heathers.'”

Ryder — who turns 41 in October (though she still looks like she’s 30) — made her official debut in the 1986 high school drama “Lucas.” The small, well-recieved role helped lead to a duo of late 1980s leads — as Lydia in “Beetlejuice” and as Veronica in “Heathers” — that propelled her to become an icon of her generation.

“I was very lucky because Tim Burton really gave me a career,” she said. “I don’t think Hollywood would’ve known what to do with me. If I hadn’t done ‘Beetlejuice,’ I think I would’ve just gone back to my school.”

Ryder also rightfully considers “Heathers” — released a year after “Beetlejuice” in 1989 — a pivotal moment in her early career.

“They didn’t want me for it,” she recalled. “I wasn’t pretty enough. I had to go a mall and get my makeup done, and then I just begged them and begged them. That was a kind of turning point because that was kind of the first movie where I’d played someone who was attractive. And then that led to a lot of films.”

But when talking to Indiewire during the Toronto International Film Festival earlier this week (where she’s promoting her latest film, Ariel Vromen’s “The Iceman”), Ryder is quick to discourage young actors currently trying to follow in her footsteps.

“If I were 18 right now, I wouldn’t want to become an actress, I know that much,” she said. “It’s just a different business now. Instant access surveillance, it’s just crazy. Now everyone wants to know everything in such a different way… I mean, there’s already so much pressure when you’re a kid. You’re uprooted and move to L.A. First they like you, then you’re told they don’t like you. It’s a lot of pressure when at the same time you’re going through puberty. But now these paparazzi literally follow people around. It’s really criminal stuff and it’s scary to me.”

While Ryder may never have had to experience the intensity of being a teen actress in today’s paparazzian landscape, she’s hardly avoided it altogether. Her relationship (and breakup) with Johnny Depp’s was most definitely the early 1990s pop-culture equivalent to Kristen Stewart and Robert Pattinson. And, of course, her 2001 shoplifting arrest didn’t exactly go unnoticed.

But Ryder has shifted her priorities as of late, finding comfort in a quieter life outside of Hollywood.

“I’m based in San Francisco and I love my life there,” she said. “I have my family and my friends. It’s equally as important to me to be a good friend, and a good sister, and a good daughter. I’m very close with my family and friends. It became all about me when I was at the height of it all in the 1990s.” Continue reading

No phoenix force driving Ryder

Winona Ryder has been working steadily for years, following a hiatus in the wake of her sensationalized shoplifting conviction dating back to an incident in 2001 at Saks Fifth Avenue in Beverly Hills. Yet many people, including media who don’t do their homework, seem to think that every new movie is a miraculous “comeback” from total obscurity.

So there was Ryder again defending herself and her career at Monday’s Toronto filmfest press conference for her latest film, the drama The Iceman. Ryder plays Deborah Kuklinski, the wife of true-life mob contract killer Richard Kuklinski, who is portrayed by Michael Shannon. The same film just screened at the Venice filmfest and Ryder said she got the same question there.

“I’ve been asked that question a bit in Venice and I don’t know if I’m developing a little bit of a complex, because I don’t know if you’re saying: ‘We missed you!’ or you’re saying: ‘What are you doing here? You’re not welcome!’ ”

Ryder, now 40 and living happily in San Francisco, said she is enjoying her age, her life and her career as an actress who works only when the role calls to her. Like it did in Ariel Vromen’s The Iceman. Continue reading

Michael Shannon casts darkness on filmdom’s latest Mafia hit man “The Iceman”

VENICE, Italy – Loving father and husband at home, a ruthless killer at work: The real-life Mafia hit man who inspired Ariel Vromen’s new film, “The Iceman,” had a steep after-work decompression curve.

“The Iceman,” which premiered Thursday in competition at the Venice Film Festival, dissects the duality of the real life of Richard Kuklinski, who for decades killed on order while keeping the truth of his occupation from tainting his perfect suburban family life.

The movie stars Michael Shannon, the film world’s latest Mafia hit man, Winona Ryder as his unsuspecting wife and Ray Liotta as the Mafia boss who sees hit-man potential in Kuklinski’s dispassionate coolness and absence of fear.

Vromen said he was captivated when he saw Kuklinski, who was arrested in 1986, tell his story a 2006 documentary. He said he found himself surprised to feel empathy for a man eventually convicted of at least 100 mob hits and who may have committed more than twice that number.

All the while, Kuklinski created an idealized home life for his wife and two daughters, whom he sent to Catholic school and took on roller skating outings.

“I couldn’t stop thinking about it, about why did I care about that really, really extreme monster? And it was haunting me, the fact that I did care, that I had a very, very deep empathy,” Vromen said in an interview.

“It was quite a challenging struggle to write a script that would be balanced enough, to show on the one hand that this is the devil, and on the other hand not try to be corny and be an apologist for a character like that.

Vromen said he fought for two years to get Shannon for the role, warding off “the obvious choices.”

“Michael Shannon comes with a darkness,” Vromen said. “If he comes with darkness, my job is to be, how can I lighten that darkness? How can I make that darkness more refined?”

In a sign that Vromen was onto something, Shannon’s two-year-old screen test for the role has gotten over 200,000 hits on YouTube. Continue reading

Timothy Leary and Winona Ryder

I am often asked about Timothy Leary, who was he, and what was his connection with Winona Ryder. Timothy Leary was the key figure in the 1960s counterculture movement and would probably be best described as a social renegade before it was fashionable to be one. He was kicked out of the West Point Military Acadmey and also dismissed from Harvard University for experimenting with hallucinating drugs on his students, and that of course, won him both notoriety and jail time. It was that whole “turn on, tune in and drop out” thing that made Leary a controversial figure some years before the entire world felt the need to go to San Francisco and put flowers in its hair.

The connection with Winona and Timothy Leary was that he was her godfather, and that came about three months after Winona was born when her father Michael Horowitz, who by then was working both as a bookseller of counterculture literature and also as Leary’s archivist.

Read more at Nigel Goodall blog.

From ‘Black Swan’ to ‘The Dilemma’: Is Winona Ryder Having a Comeback?

Back in the late ’80s and early ’90s, Winona Ryder won audience’s hearts for being quirky and dark, with films like 1988’s ‘Beetlejuice’ and 1990’s ‘Edward Scissorhands’ (both helmed by Tim Burton) and, my personal favorite, 1989’s ‘Heathers.’ She made her mark as the first “manic pixie dream girl” — sure, she’s slightly different, but you can’t help but fall in love with her.

Ryder’s expressive, big eyes and penchant for sad, relatable characters made her super lovable. As the young emo-goth Lydia Deetz in ‘Beetlejuice,’ one of her first roles, she gained stand-out praise alongside established actors Michael Keaton and Alec Baldwin.

Her follow-up, as Veronica Sawyer, in the super-dark high school satire ‘Heathers,’ solidified her place as a movie star.

In 1994, Ryder won a Golden Globe Award for Best Supporting Actress and an Academy Award nomination for her role in ‘The Age of Innocence.’ She was nominated again for the Best Actress Oscar in 1995 for ‘Little Women.’ Then she showed real chops in 1999’s ‘Girl, Interrupted,’ holding her own against Angelina Jolie’s tour-de-force performance and really making an impact on audiences. In 2000, Ryder was honored with a star on the Hollywood Walk of Fame. Continue reading

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