Hollywood is a weird place where friendships usually last about as long as a juice cleanse. But then you have Leonardo DiCaprio and Tobey Maguire. These two have been attached at the hip for over 35 years. Honestly, it’s kinda wild when you think about it. Most people know they’re friends, but the actual story of how they met—and the messy stuff they’ve survived together—is way more interesting than just two famous guys sitting courtside at a Lakers game.
The "I Want to Be His Friend" Moment
They weren't born into royalty. They were just two kids with single moms in Los Angeles, hitting the same soul-crushing auditions in the late '80s.
Leo saw Tobey first.
DiCaprio famously recalled the moment he saw Maguire on a film set or at an audition (the details vary, but the vibe is the same). He literally jumped out of his car and shouted, "Tobey! Tobey! Hey! Hey!"
Tobey’s reaction? Basically: "Who is this kid?"
He was 12. Leo was 12. They made a pact right then and there. They decided that instead of being rivals for the same "scrawny kid" roles, they’d help each other out. If one got a part, he’d pull the other one in.
They actually kept that promise.
When Leo got the lead in This Boy’s Life (1993) alongside Robert De Niro, he made sure Tobey got a part as one of his friends. It was a small role, but it set the template. They weren't competing; they were a team.
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The Infamous "Pussy Posse" Years
You can't talk about Leonardo DiCaprio and Tobey Maguire without mentioning the '90s. Specifically, the "Pussy Posse."
That was the actual name. Yeah, it’s cringey.
The group included guys like Kevin Connolly (from Entourage), Lukas Haas, and David Blaine. They were the kings of New York and LA. They’d crash Victoria’s Secret parties, start literal fights in restaurants, and act like the world belonged to them.
One story involves an actor named Roger Wilson. He allegedly got into a scrap with the group because they were hitting on his girlfriend, Elizabeth Berkley. Someone—reportedly from the posse—ended up punching Wilson in the larynx.
It was peak "young, rich, and obnoxious" behavior.
Then there’s Don’s Plum. This is the movie they desperately don’t want you to see. It’s a black-and-white indie film shot in the mid-90s where they basically play versions of themselves. The characters are misogynistic, aggressive, and kinda mean.
Leo and Tobey sued to stop it from being released in the US. They claimed it was only supposed to be a short film.
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To this day, you can’t officially watch it in America. It’s the "lost" DiCaprio movie.
High Stakes and "Molly’s Game"
As they got older, the partying changed. It became about high-stakes poker.
If you’ve seen the movie Molly's Game, the character "Player X" (played by Michael Cera) is widely believed to be based on Tobey Maguire. According to Molly Bloom’s memoir, Tobey was a "degenerate" gambler—but a very smart one.
He didn't just play; he controlled the games.
- He allegedly made Molly "bark like a seal" for a $1,000 tip.
- He brought his own $17,000 shuffling machine and charged the game to use it.
- Leo was often there, but mostly as the "lure" to get billionaires to stay at the table.
Tobey was the shark. Leo was the bait.
Reunited on Screen: The Great Gatsby
It took 20 years for them to share a major screen again. When Baz Luhrmann was casting The Great Gatsby (2013), Leo didn't just suggest Tobey for the role of Nick Carraway—he basically demanded it.
It was perfect casting.
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Gatsby is the mysterious superstar, and Nick is the loyal friend watching from the sidelines. That’s their real-life dynamic in a nutshell. Leo is the global icon, the guy on the posters. Tobey is the one who’s always there, just out of the spotlight, keeping the secrets.
Is the Friendship Crumbles?
Recently, there’s been some tabloid noise. In late 2025 and early 2026, reports surfaced that Tobey felt "left out" because Leo started hanging out heavily with Sean Penn.
Is it true? Who knows.
But even with the rumors, they were spotted together over Thanksgiving. They’ve survived the '90s tabloids, a banned movie, underground gambling rings, and dozens of breakups. (Tobey is often seen on yachts with Leo and whatever 22-year-old model he's dating at the time).
Why This Matters for You
The takeaway from the Leonardo DiCaprio and Tobey Maguire saga isn't just "fame is crazy." It's about the "Pact."
- Find your "car-jump" person. Someone you’re willing to look like an idiot for.
- Eliminate rivalry. In any industry, you’ll go further if you treat your peers as collaborators rather than threats.
- Keep the circle tight. Longevity comes from loyalty, even when you're both at the top of the mountain.
If you want to see their chemistry for yourself, skip the gossip sites. Go back and watch This Boy's Life to see where it started, then watch The Great Gatsby to see how far they came. It’s rare to see two people grow up in public without tearing each other down. That, more than the movies, is their real legacy.
Check out the original New York Magazine "Leo, Prince of the City" profile if you want to see the raw, unpolished version of their '90s era—it's a time capsule of a Hollywood that doesn't really exist anymore.