You remember that poster, right? The one with the golden Central Park leaves, Richard Gere looking suave but soulful, and Winona Ryder with that pixie cut, looking like she was about to break into a million pieces. It was 2000. The world was obsessed with "May-December" romances, and on paper, this was the ultimate pairing. A silver fox and the "it girl" of the nineties.
But then the movie actually came out.
Richard Gere and Winona Ryder in Autumn in New York wasn't just a movie; it was a vibe that somehow went completely sideways. Critics absolutely shredded it. Even now, twenty-six years later, it’s one of those films people find themselves hate-watching on a rainy Sunday because the chemistry—or lack thereof—is just so fascinatingly weird.
The Movie That No One Wanted to Review
Here’s a fun piece of trivia: MGM was so terrified of what critics would say that they skipped the advance screenings. That’s usually the "kiss of death" in Hollywood. It’s the studio basically saying, "We know it’s bad, please just let us make some money before the reviews hit the papers."
Richard Gere and Winona Ryder weren't happy about it. They actually went public, objecting to the studio's lack of confidence. Honestly, you've gotta respect the hustle. They stood by their work, even when the script had Gere playing a 48-year-old restaurateur named Will Keane who falls for a 22-year-old girl who—surprise!—is the daughter of an old flame.
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Oh, and she’s dying. Of course, she is. It’s a tearjerker.
Why the Chemistry Felt Off
A lot of people complain about the age gap. In the film, Gere is nearly 50 and Ryder is 22. In real life, the gap was similar—Gere was 50 and Ryder was 28 during filming. But the problem wasn't the years; it was the energy.
Gere was in his "zen" phase. He was playing this smooth, detached playboy who finally learns how to feel. Ryder was playing Charlotte, a "free spirit" who makes hats with bug antennae on them and says things like, "I can smell the rain."
Critics like Emanuel Levy called it "utterly banal." The dialogue felt like it was written by a first-grader trying to sound like a poet. When they first dance, Gere tells her, "Man, you don't dance, you float." It’s kinda cringey, honestly.
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- The Director's Cut: Joan Chen, the director, actually had her version of the film heavily re-edited by the studio.
- The Nude Scene: There was originally a nude scene featuring Ryder that MGM chopped out to keep the PG-13 rating.
- The Writer’s Wrath: Screenwriter Allison Burnett famously bashed Gere in interviews, basically accusing him of ruining the film by demanding changes.
Rumors of Off-Screen Drama
Because the on-screen romance felt a bit wooden, the tabloids went into overdrive. There were rumors that the two leads couldn't stand each other. People said Gere was demanding more lines and that Ryder was over the whole thing.
Winona eventually cleared the air. She told the Sunday Express that the rumors were "ridiculous" and "stupid." She pointed out that since they were in 90% of the scenes together, it wouldn't even make sense for him to ask for more screen time.
Gere, ever the Buddhist, took the bad reviews in stride. He later said that in a long career, you realize you can't hit a home run every time. That’s a pretty healthy way to look at a movie that currently sits with a 15% on Rotten Tomatoes.
The Real Stars of the Film
If you watch it now, the best parts aren't even the leads. Elaine Stritch plays Winona’s grandmother, and she is a force of nature. She’s tough, she drinks, and she has zero time for Richard Gere’s nonsense.
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Then there’s Vera Farmiga. She plays Gere’s illegitimate daughter. It’s a small role, but she brings a groundedness to the movie that the main romance desperately lacks.
The Legacy of a "Flop"
Despite the critics, Autumn in New York actually doubled its budget at the box office, raking in about $90 million worldwide. People love a good cry, even if the movie is "sappy."
It captured a very specific version of New York City that feels like a time capsule now. Pre-9/11, golden-hued, filled with expensive overcoats and rooftop Halloween parties. It’s basically a love letter to Manhattan dressed up as a tragic romance.
What You Can Learn from the Richard Gere and Winona Ryder Pairing
If you're looking back at this era of cinema, there's a few things that stand out about why this movie didn't quite become the next Love Story.
- Casting matters more than names. Putting two huge stars together doesn't guarantee a spark. Sometimes, their "acting styles" just clash.
- Studio interference kills vision. We’ll never know if Joan Chen’s original, more "artistic" version would have worked better than the soap opera we got.
- The "May-December" trope has aged poorly. In 2000, the age gap was a plot point. In 2026, it often feels more like a "red flag" for the male lead's character.
If you’re planning a movie marathon, don’t skip this one, but go in with the right expectations. It’s not a masterpiece, but it’s a fascinating look at a moment in time when Hollywood was trying to manufacture "classic romance" and ended up with something much weirder.
Next Steps for Film Fans:
Check out Joan Chen’s earlier film, Xiu Xiu: The Sent Down Girl, to see what she's capable of when a studio isn't breathing down her neck. If you want to see Gere at his best, revisit Internal Affairs or Chicago. For Ryder, Girl, Interrupted—released just a year before Autumn—shows the incredible range she had during that same period.