9 Fun Facts About Leonardo DiCaprio and Tobey Maguire's 30-Year Friendship

Leo and Tobey's friendship has spanned decades. In an interview with Esquire, Leo reminisced about the first time he ever met Tobey, back when he was a struggling 12-year-old actor. "I literally jumped out of the car. I was like, 'Tobey! Tobey! Hey! Hey!' And he was like, 'Oh, yeah — I know you. You're . . . that guy.' But I just made him my pal. When I want someone to be my friend, I just make them my friend."

In their early Hollywood days, Leo and Tobey ran with a group of guys who were reportedly known as "The P*ssy Posse." The bunch, who they still spend time with, includes Kevin Connolly, magician David Blaine, Lukas Haas, and others.

Leo made his film debut in Critters 3, a role which he got at Tobey's expense. In 1993's This Boy's Life, Leo also beat out Tobey for the main role, but this time around Tobey ended up getting a part as one of Leo's friends in the film. Fortunately neither incident stopped the two from becoming close, and they went on to collaborate on two movies years later: the ill-fated, low-budget Don's Plum in 2001, and The Great Gatsby in 2013.

When Leo wanted to discuss Tobey being a part of Baz Luhrmann's The Great Gatsby, he didn't have to wait long for a meeting with his longtime pal. "I happened to live next door to Leo at the time, so it wasn't a far journey," Tobey said in a 2013 interview. "I was like, 'Oh, yeah. Sure. I can be over in 30 seconds if that's good for you.'"

A few years ago Tobey told People that their A-list friendship isn't as glamorous as you might think. "We are like any other buddies. There's a lot of laughing and chatting between us. We enjoy doing a lot of things we have in common, like basketball. We like to play and talk about basketball."

The two were so close on set that even director Baz Luhrmann couldn't help but describe their bond as "a true partnership." Leo and Tobey ended up being invaluable resources for each other while filming the 2013 adaptation, especially when it came time to dole out "brutally honest" opinions. "I can't tell you how many countless times on set we would do a scene and come up to one another and say, 'What's your take on that? What was I doing, do you think?'" Leo said. "We had our own very distinct private conversations about everything."

As the 25+ years can attest, Leo and Tobey's friendship definitely isn't some Hollywood fling. “Leo and I have a lot of trust and respect for each other,” the Spider-Man actor told People. "We have a close friendship and I definitely have an affection for Leo."

Like all good friends, the two turn to each other whenever they find themselves in need of some advice. "Every project we do, we talk about," Leonardo told the Associated Press. "Every single choice I've made, I've talked to Tobey about and vice versa. We've had endless conversations about certain projects and argued with one another and supported one another along the way."

When it comes to hanging out with Tobey's kids (whom he shares with estranged wife Jennifer Meyer), Ruby and Otis, apparently Leo acts like a natural." He "tags along for more family friendly activities with Tobey, his wife and kids,” a source told People in 2016. “They will visit the beach, or grab Sunday brunch. Leo is great with Ruby and Otis . . . He is very hands-on, too, and offers help with cutting up their food and will carry them across the street. He would be a great dad!" Leo was also named Ruby's godfather in 2006.