Hollywood is a weird place where the math usually involves pairing the "It Girl" of the moment with a leading man who looks like he spends four hours a day at the gym. But back in the early 2000s, we got something different. We got Winona Ryder and Adam Sandler.
It’s been over two decades since Mr. Deeds hit theaters in 2002. At the time, critics basically had a collective meltdown. They hated it. They nominated both of them for Razzies. They called it "stale" and "indifferently acted." But here’s the thing: those critics were mostly wrong. Looking back from 2026, the connection between Winona and Adam represents one of the most genuine, if slightly chaotic, friendships in the industry.
The Night Calls and the Broken Arm
You might think of them as just co-stars who cashed a check and moved on, but their bond actually goes way deeper. Winona has been open about the fact that they are both chronic insomniacs. Honestly, there’s something kind of sweet about the image of two of the biggest stars on the planet calling each other at 2:00 AM just because they can't sleep.
Winona once told W Magazine that she just "loves him so much." She wasn't talking about a romance—Sandler has been with his wife, Jackie, forever—but about a level of character. She called him one of the most generous people she’s ever known.
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And she literally bled for that movie. Well, she broke a bone, anyway. During the filming of Mr. Deeds, there’s a scene where they’re riding bikes down a flight of stairs in Central Park. Winona was wearing heels. Her heel caught in the pedal, and boom—first broken bone of her life.
Why Mr. Deeds Is Better Than You Remember
If you haven't rewatched it lately, you're missing out on some top-tier 2000s vibes. Is it high art? No. It’s an Adam Sandler movie. But Winona Ryder brings a weirdly grounded energy to the role of Babe Bennett, the tabloid reporter who goes undercover as a "school nurse" to scoop Deeds.
Most "Sandler girls" are there to look pretty and laugh at his jokes. Winona felt like she was in on the bit. She was transitioning from being the dark, edgy queen of Heathers and Beetlejuice into what she called "flat-out Sandleresque humor."
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- The Chemistry: It’s not "steam-up-the-windows" sexy. It’s "we-could-eat-pizza-at-midnight" comfortable.
- The Satire: The movie actually makes some decent points about how cynical the media can be—points that feel even more relevant now in the age of 2026 social media than they did in 2002.
- The Support: When Winona was going through her well-documented "difficult" period in the early 2000s, Sandler didn't distance himself. He’s known for being fiercely loyal to his friends, and Winona was firmly in that circle.
The "Destination Wedding" Confusion
There’s a bit of a Mandela Effect happening online where people keep thinking Winona and Adam reunited for the 2018 flick Destination Wedding. Let’s clear that up: that was Winona and Keanu Reeves.
However, the reason people get it mixed up is because the vibe is so similar. People want to see Winona with guys who have that same "misfit" energy. Sandler and Ryder both occupy this space where they are massive stars but also feel like they don't quite fit the standard Hollywood mold. He’s the guy in the oversized basketball shorts, and she’s the girl who still looks like she’s listening to The Replacements on a walkman.
What Most People Get Wrong About Their Career Paths
People love to say Winona’s career died and then was resurrected by Stranger Things. That’s a bit of a lazy narrative. She was always working, just choosing things that weren't $100 million blockbusters.
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Similarly, people used to dismiss Sandler as just a "goofball." But after Uncut Gems and Hustle, the world finally realized what Winona saw back in 2002. She famously said she saw "greatness" in him and that he "moved" her as an actor. She saw the dramatic chops long before the Oscars did.
Real Talk: The Legacy of the Duo
Looking at Winona Ryder and Adam Sandler today, it’s a reminder that Hollywood doesn't always have to be about "prestige." Sometimes it’s about two people who genuinely like each other making something that makes people feel good. Mr. Deeds made over $171 million at the box office for a reason. Audiences didn't care about the 22% Rotten Tomatoes score; they cared about the heart.
If you’re looking to revisit this era of pop culture, don’t just look at the movies. Look at the interviews. Look at the way they talk about each other. It’s a masterclass in how to maintain a professional relationship that actually turns into a real-life support system.
How to Appreciate This Era Today
- Watch the Behind-the-Scenes: There’s a lot of footage of the Central Park bike accident and the fire-gel stunts. It shows how "game" both of them were for the physical comedy.
- Look for the Nuance: Pay attention to Winona’s face in the scenes where she’s "lying" to Deeds. She plays the guilt better than most actors would in a broad comedy.
- Ignore the Razzies: Both were nominated for Worst Actor/Actress. In hindsight, those nominations feel mean-spirited and totally out of touch with what the movie was trying to be.
The next time you're scrolling through a streaming service and see that yellow poster for Mr. Deeds, give it another shot. It’s not just a relic of the early 2000s; it’s the origin story of a friendship that has quietly outlasted most Hollywood marriages.
Actionable Insight: If you're a fan of either actor, check out the 2002 W Magazine interview with Winona. It’s one of the most honest looks at her headspace during that time and her genuine affection for Sandler. Also, keep an eye on Happy Madison’s upcoming slate; with the way Sandler brings back his favorite people, a 2026/2027 reunion project with Ryder isn't just wishful thinking—it's actually pretty likely.