You've probably seen the photos. Two of the biggest stars on the planet, hidden under baseball caps, sitting courtside at a Lakers game or hanging out on a yacht off the coast of France. Tobey Maguire and Leonardo DiCaprio are basically the ultimate Hollywood "best friend" goals. They’ve been tight for over thirty years, which is roughly three centuries in "fame years." But here is the weird thing: despite being inseparable in real life, their professional overlap is actually pretty tiny.
Most people think they have a dozen movies together. Honestly? They don't.
If you try to count the number of times they’ve shared the screen, you’ll run out of fingers before you even get through a single hand. It is a strange quirk of their careers. They made a pact as kids to help each other out, yet they’ve mostly operated in totally different cinematic universes. One became the definitive Peter Parker; the other became the king of the "prestige" Oscar drama.
When they do work together, though, things get interesting. Or, in one specific case, things get legally messy.
The Great Gatsby: The One Everyone Remembers
In 2013, Baz Luhrmann finally gave the world what it wanted. He cast the two real-life best friends as on-screen best friends in The Great Gatsby. It was perfect casting, really. Leo played the mysterious, ultra-wealthy Jay Gatsby, and Tobey was Nick Carraway, the wide-eyed narrator who watches the whole tragedy unfold.
There is a specific energy in that movie that you just can't fake. When Nick looks at Gatsby with that mix of awe and concern, you’re seeing thirty years of genuine history. Leo actually called Tobey personally to ask him to do the part. Imagine getting that phone call. "Hey, want to come to Australia and wear fancy suits and throw fake parties for five months?" Easy yes.
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The movie was a massive hit, making over $350 million. Critics were split—some loved the hip-hop soundtrack and the 3D glitter, others thought it was too much—but nobody denied the chemistry between the two leads. It remains the most famous example of a Tobey Maguire and Leonardo DiCaprio movie that you can actually find on a streaming service without a lawsuit attached to it.
Don’s Plum: The Secret Movie They Tried to Delete
Now, let's talk about the one they don't want you to see. If you’ve never heard of Don’s Plum, there is a very good reason for that. Leonardo DiCaprio and Tobey Maguire spent years in court trying to make sure this film never saw the light of day in the United States or Canada.
Back in the mid-90s, before Titanic turned Leo into a god and before Tobey was biting spiders, they were part of a group of young actors often called the "Pussy Posse" (a name they supposedly hated, but it stuck). They spent a couple of nights in 1995 and 1996 filming this low-budget, black-and-white indie drama. It was mostly improvised. The premise? A bunch of guys sitting in a diner talking about girls, sex, and life.
Why the Lawsuit?
The actors claimed they thought it was just a short film or an acting exercise. The producers, however, edited it into a feature-length movie. As Leo and Tobey’s stars began to rise, they reportedly got worried. The characters in Don's Plum are... well, they’re jerks. They say offensive things. They act like arrogant teenagers.
- Reputation Management: They didn't want their "clean" images ruined by a gritty indie film.
- Legal Battles: A lawsuit in 1998 led to a settlement that banned the film from being released in North America.
- The Internet Leak: In 2014, one of the producers uploaded it to the internet for free. It was taken down almost immediately after a copyright strike from the actors.
It’s a fascinating bit of Hollywood history. It’s the "lost" movie. You can find clips of it on YouTube if you look hard enough, but it remains a legal ghost. It’s the ultimate "what if" of their early careers.
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This Boy’s Life: Where It All Began
We have to go back to 1993 to see the very first time they shared a set. This Boy's Life is mostly known as the movie where Leonardo DiCaprio held his own against Robert De Niro. It’s a heavy, intense drama about an abusive stepfather.
Tobey Maguire is in it too, but you might blink and miss him. He plays a character named Chuck Bolger, one of Leo’s friends. This was actually the start of their "pact." They both auditioned for the lead role of Toby Wolff. Leo got the part, but he allegedly pushed for his friend Tobey to get a role in the film as well.
It wasn't a huge box office smash—it only made about $4 million—but it’s the DNA of their friendship. It’s where they proved they could work together without the competition ruining their bond.
Why Haven't They Done More?
It's a question fans ask all the time. If they're such good friends, why aren't they the modern-day Matt Damon and Ben Affleck?
Part of it is just the types of movies they choose. Leo is very selective. He works with Scorsese, Tarantino, and Inarritu. Tobey took a long break from acting after the Spider-Man trilogy and Brothers, focusing more on producing. They have very different "brands."
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There is also the risk of the friendship overshadowing the story. If they’re in every movie together, the audience just sees "Leo and Tobey" rather than the characters. By keeping their collaborations rare, they make movies like The Great Gatsby feel like a genuine event.
What You Should Watch Next
If you're looking to dive into the Tobey Maguire and Leonardo DiCaprio movie catalog, you have a very specific roadmap. You can't just binge-watch a dozen films. You have to be intentional.
Start with The Great Gatsby. It’s the peak of their professional relationship. Then, go back to This Boy's Life to see the raw, young talent before the fame took over. If you're feeling adventurous and can navigate the darker corners of the web, try to find a bootleg of Don's Plum just to see why they were so desperate to hide it.
- Check out the 2013 Gatsby soundtrack: It’s still one of the best "modern-meets-vintage" albums out there.
- Look for their 2026 rumors: There have been whispers in Hollywood circles about a potential production collaboration where Tobey produces and Leo stars, though nothing is set in stone yet.
- Watch their interviews together: Specifically the ones from the Gatsby press tour. Their comfort level with each other is actually pretty hilarious to watch compared to standard, stiff actor interviews.
The reality of their "joint" filmography is that it’s less about the quantity and more about the legend. Their friendship is the real blockbuster. The movies are just the occasional spin-offs.