It was 1998. Bill Clinton was in the White House, "Iris" by the Goo Goo Dolls was playing on every radio station, and two young actors named Reese Witherspoon and Tobey Maguire were about to make film history in a town where nothing ever happened.
Funny how time works.
Today, Reese is a billionaire media mogul with an Oscar on her shelf. Tobey is the definitive Peter Parker who recently swung back into the zeitgeist. But back then? They were just two rising stars playing twin siblings in a black-and-white world that was literally waiting for them to bring the color.
If you’ve spent any time on TikTok or X lately, you’ve probably seen the rumors. People love to dig up old pairings. They want to know if these two ever dated, if they’re still friends, or if there’s some secret feud buried under decades of Hollywood gloss.
Honestly, the reality is a lot more grounded than the tabloids want you to think.
The Pleasantville Connection: Where It All Started
Before the spider-bites and the "Legally Blonde" courtroom scenes, there was Gary Ross's Pleasantville. It’s a weird, beautiful movie. Tobey plays David, a 90s kid obsessed with 1950s reruns. Reese plays Jennifer, his sister who’s more concerned with, well, everything else.
They get sucked into a TV. It sounds like a Disney Channel premise, but it’s actually a pretty heavy metaphor for repression and social change.
Working together on that set wasn't easy.
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Because of the groundbreaking visual effects, they had to film the entire movie in color while wearing green makeup so editors could turn them black-and-white later. Imagine looking at your co-star and seeing a literal swamp creature while trying to deliver a heartfelt monologue about 1950s family values.
Reese and Tobey had to sell a sibling dynamic that felt lived-in. They did. David was the cautious nerd; Jennifer was the firecracker. It’s a dynamic that defined their early careers.
Why people think they dated
Hollywood loves a "showmance." When you have two attractive people on a press tour, the questions start. "Are you guys together?" "Is there a spark?"
Back in the late 90s, the rumor mill was convinced something was happening. They were spotted at events together. They had that easy, comfortable chemistry that usually implies more. But here’s the thing: they were part of a very specific "Young Hollywood" circle.
- Leonardo DiCaprio
- Paul Walker (who was also in Pleasantville)
- Lukas Haas
Tobey was a core member of the "Pussy Posse" (yes, that was their real, cringey name for the friend group). Reese was the southern belle trying to break out of the "cute girl" mold. They hung out, sure. They probably shared a few late-night dinners at Jerry’s Deli. But the "dating" part? It’s mostly just fan fiction from a pre-social media era.
The Path Diverged: Two Very Different Careers
After Pleasantville, they went in totally opposite directions. Reese became the "Queen of Rom-Coms" before pivoting into one of the most powerful producers in the industry. Tobey became a superhero.
Reese Witherspoon's Rise
Reese didn't just act. She built. By the time she founded Hello Sunshine, she was basically telling Hollywood what women wanted to watch. She’s the person responsible for Big Little Lies and The Morning Show. She’s not just a "star" anymore; she’s the boss.
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Tobey Maguire’s Quiet Period
Tobey’s path was... quieter. After the Sam Raimi Spider-Man trilogy ended, he stayed out of the spotlight. There were stories about high-stakes poker games (look up Molly’s Game if you want the tea). He did some producing, some indies, but mostly he just became a dad and a guy who really likes his privacy.
It’s probably why people are so obsessed with his old connections. When someone goes "ghost," we start looking at who they used to know.
Are Reese and Tobey Still Friends Today?
It’s the question that drives the Google searches. In 2026, the answer is "Hollywood friendly."
They aren't posting selfies on a boat in Italy together. You won't find them doing a "Besties" Vogue interview. But when they cross paths at industry events—like the Oscars or the SAG Awards—there’s an obvious warmth there.
Think about your high school friends. You don’t talk to them every day. You might not even have their new number. But if you see them at a grocery store, you’re going to spend twenty minutes catching up because you went through something intense together.
For Reese and Tobey, Pleasantville was their high school. It was the moment they both realized they were going to be "Big Deal" actors.
The Paul Walker Link
There’s a shared grief that keeps that old cast connected. Paul Walker played Skip Martin in Pleasantville—the basketball star who falls for Reese’s character. When Paul passed away in 2013, it hit that entire 90s cohort hard. It’s those kinds of moments that solidify a bond between actors, even if they haven't worked together in twenty years.
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Addressing the Misconceptions
People get a lot of stuff wrong about these two.
- They didn't hate each other. There were some old blinds claiming they clashed on set because Tobey was "too serious" and Reese was "too bubbly." Total nonsense. Gary Ross has gone on record saying they were incredibly professional.
- Pleasantville wasn't a flop. While it didn't break the box office initially, it's considered a masterpiece of cinematography today. It’s studied in film schools.
- They haven't worked together since. This is actually true and kind of a bummer. Despite both being heavy hitters, their projects haven't overlapped.
What You Can Learn from Their Careers
If you’re looking for a takeaway from the Reese-Tobey saga, it’s about longevity.
In an industry that eats people alive, they both survived. Reese did it by taking control of the narrative. Tobey did it by stepping back when he needed to. They represent two different ways to "win" at life.
If you want to revisit the magic, go back and watch Pleasantville. Don't just look at the effects. Look at the way they play off each other. It’s a masterclass in subtlety from two people who were barely twenty years old.
The Next Steps for a Fan:
- Watch the "The Art of Pleasantville" featurette. It shows the insane green-makeup process they went through.
- Follow Hello Sunshine. If Reese and Tobey ever do reunite for a project, it'll likely be under her production banner.
- Check out Tobey's production credits. He’s been involved in more movies lately than you might realize, often staying behind the scenes.
Hollywood is a small town. Eventually, David and Jennifer Parker will probably share a screen again. Until then, we’ve got the 1998 classic and a lot of nostalgia to keep us going.