Hollywood is a small town. Seriously. People think it’s this sprawling metropolis of disconnected stars, but if you’ve been in the game as long as Natalie Portman and Tobey Maguire, you’ve basically grown up in the same sandbox.
Most fans only remember them together for that gut-wrenching 2009 war drama Brothers. You know the one—where Tobey goes full "thousand-yard stare" and Natalie has to play the emotional anchor of a family falling apart. But their history actually goes back way further than a film set in New Mexico.
The 1996 Meeting You Didn’t Know About
Here’s a fun piece of trivia: Natalie Portman and Tobey Maguire met when she was just 14 years old.
It wasn't at some glitzy Oscar party or a high-stakes table read. They actually crossed paths in 1996 at the Directors Guild Theatre. They were both attending the premiere of The Pallbearer, a David Schwimmer movie. Imagine that for a second. A pre-fame (mostly) Tobey and a post-Leon: The Professional Natalie just hanging out at a mid-90s premiere.
They’ve been tight ever since.
Honestly, it’s rare to see that kind of longevity in celebrity friendships. Natalie has mentioned in interviews that by the time they got around to filming Brothers, there was already this deep level of familiarity. She also knew Jake Gyllenhaal since she was 18. So, when you see the tension and the "family" vibe on screen, it’s not just great acting. It’s decades of actual history.
👉 See also: Jesus Guerrero: What Really Happened With the Celebrity Hair Stylist Death Cause
What Really Happened During "Brothers"?
If you haven't seen Brothers, it’s heavy. Tobey plays Sam Cahill, a Marine who is presumed dead in Afghanistan. Natalie plays his wife, Grace. While Sam is gone (and being tortured), his "screw-up" brother Tommy (Jake Gyllenhaal) steps in to help Grace and the kids.
The chemistry was so intense that the tabloids went into a bit of a frenzy back in 2009. There were rumors. There’s always rumors.
But the reality was much more professional—and a little bit scary. Tobey Maguire’s performance was so volatile and raw that it reportedly unsettled Natalie on set. There’s a specific scene at a kitchen table that people still talk about in acting classes. Tobey’s character is losing his mind with PTSD-fueled jealousy, and the fear you see on Natalie’s face?
That wasn't just in the script.
She’s admitted that Tobey’s commitment to the role blurs the lines. He lost a significant amount of weight and stayed in that dark headspace. It paid off, though. Tobey snagged a Golden Globe nomination, and many critics still argue it’s the best thing he’s ever done. Even better than the Spidey suit.
✨ Don't miss: Jared Leto Nude: Why the Actor's Relationship With Nudity Is So Controversial
Addressing the Dating Rumors
Let's clear the air. Did they date?
Basically, no. While the internet loves to ship co-stars, Natalie Portman and Tobey Maguire have always been "just friends." In fact, during the height of the Brothers press tour, Tobey was married to Jennifer Meyer. There was even a funny, slightly awkward story about Jennifer being "bombarded" with questions about her husband's intimate scenes with Natalie.
Tobey had to reassure her it was all just work.
Natalie, meanwhile, met her future husband, Benjamin Millepied, shortly after on the set of Black Swan. So, while their onscreen marriage was a tragic mess of secrets and trauma, their off-screen relationship is just a boringly healthy, long-term Hollywood friendship.
Why Their Connection Still Matters in 2026
It’s been over fifteen years since they shared the screen, yet people are still obsessed with their dynamic. Why?
🔗 Read more: Jada Pinkett Smith With Hair: What Most People Get Wrong About Her Journey
Part of it is the "Child Star Success" factor. Both of them started incredibly young. They navigated the pitfalls of early fame without the public meltdowns that claimed so many of their peers. Natalie went to Harvard; Tobey became a world-class poker player (and Spider-Man).
They represent a specific era of "prestige" Hollywood that feels increasingly rare.
Key Takeaways from Their Professional Arc:
- Longevity is possible: You can be friends for 30 years in Hollywood without a "falling out" headline.
- Method acting has costs: Tobey's intensity in Brothers created a masterpiece but was clearly taxing for his co-stars.
- Privacy works: Both actors have kept their personal lives relatively shielded, which is probably why we still respect their craft.
What You Should Do Next
If you want to see the peak of their collaboration, go back and watch Brothers. Don't just watch the clips on YouTube; watch the whole thing to see how Natalie builds the emotional stakes that Tobey eventually knocks down.
Also, keep an eye on the 2026 production cycles. With the recent trend of "legacy" pairings, there have been whispers in industry circles about the two looking for a project that doesn't involve war-time trauma—maybe something a bit lighter this time.
Check out Natalie’s recent production work with her company, MountainA, as she’s been increasingly focused on choosing projects that reunite her with old friends. If you're a fan of either, looking into their respective production choices gives you a better idea of where they're heading than any tabloid ever will.