Skip Nav
Gift Guide
POPSUGAR Editors' Gift Guide: 150+ Presents For Everyone on Your List
Jennifer Hudson
Jennifer Hudson's Son Is Too Cool For School at the Sing Premiere
Bella Hadid
50 Seriously Sexy Victoria's Secret Fashion Show Photos You Need to See

Tobey Maguire and Leonardo DiCaprio's Friendship

Leo and Tobey: Best Friends Forever

Leonardo DiCaprio and Tobey Maguire share the big screen as pals Jay Gatsby and Nick Carraway in The Great Gatsby, which hit theaters last week and premiered at the Cannes Film Festival on Wednesday, but their real-life relationship started long ago. Leo and Tobey have been friends for 25 years, after meeting at an audition in the late '80s.


Leo Recalls Their First Meeting Fondly

"After I met Tobey at an audition, I felt like I wanted this guy to be my friend. I remember driving back from school and he was doing Hot Rod Brown Class Clown with Whoopi Goldberg outside Hollywood High. It was a high school. And I jumped out of my car in the middle of the scene, as they were shooting, practically." Leo added, "I was like, 'Tobey! Tobey! Tobey! Give me your number.' He was like, 'Yeah, who are you again?'"

Fame/Flynet="inline left" />

They're Part of a Bigger Group


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.

They're Just Your Average Pals

Splash News Online

Tobey told People earlier this month: "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."

They Look to Each Other For Advice


Leo told HuffPost Entertainment that "every project we do, we talk about. 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."

They Collaborated on The Great Gatsby

Bauer Griffin Online

Leo said: "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?' We had our own very distinct private conversations about everything."

Leo's "a Good Uncle" to Tobey's Kids

Around The Web
Join The Conversation
Best Celebrity Moments of 2016
Leonardo DiCaprio's Award Show Evolution
Leonardo DiCaprio on The Ellen Show November 2016
Leonardo DiCaprio Documentary Before the Flood on YouTube
Leonardo DiCaprio Finally Addresses His Foundation's Fraud Allegations
Leonardo DiCaprio at Before the Flood Premiere in Paris 2016
Leonardo DiCaprio and Nina Agdal at the Griffith Observatory

POPSUGAR, the #1 independent media and technology company for women. Where more than 75 million women go for original, inspirational content that feeds their passions and interests.

From Our Partners
Latest Celebrity & Entertainment
All the Latest From Ryan Reynolds