“I wanted this guy to be my friend”: Leonardo DiCaprio Was So Smitten by Marvel Star He Jumped Out of the Car to Get His Number

The friendship between Leonardo DiCaprio and Tobey Maguire is an understated gem in Hollywood.

The pair who started pretty early in the industry have both earned extraordinary praise and respect from their peers for their work and contribution to cinema.

And while DiCaprio’s reputation precedes him in the best way possible, leaving a straight-up impression in the audience’s minds with his breathtaking, unforgettable, and headstrong roles, the effect that Tobey Maguire has on people is unyielding, enduring, and immense in its magnitude for his ability to be classically relevant.

Tobey Maguire and Leonardo DiCaprio.

Leonardo DiCaprio and Tobey Maguire’s Unusual Friendship

During an audition for Parenthood, Leonardo DiCaprio came across a fellow child actor, Tobey Maguire, who would soon go on to become his most enduring and lasting friend in the industry, through thick and thin.

The pair’s tight-knit friendship then eventually grew and led to 3 more people joining their pack that DiCaprio famously named the “P–sy Posse.” The posse included rapper Q-Tip, actor Luke Haas, and director Harmony Korine.

About their first meeting, DiCaprio was recorded telling The Associated Press:

“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.

I was like, ‘Tobey! Tobey! Tobey! Give me your number.’ He was like, ‘Yeah, who are you again?’.

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.”.

Leonardo DiCaprio and Tobey Maguire as teenagers.
Despite their close bond, the actors ended up with vastly different career arcs, each becoming an A-lister in their own right.

While Leo DiCaprio managed to leave an impression on an already impressed Robert De Niro, who handpicked him for This Boy’s Life, Maguire went on to earn roles in relatively successful films throughout his career.

The pair eventually starred together in Baz Luhrmann’s The Great Gatsby in 2013.

Leonardo DiCaprio and Tobey Maguire’s Hollywood Careers

Leonardo DiCaprio, as well as Tobey Maguire, started early in Hollywood, with the former leaving an indelible impression as a child actor with projects such as Growing Pains, This Boy’s Life, and What’s Eating Gilbert Grape?

His transformation into a coveted actor as he grew older remained one of the most miraculous and successful transitions in the industry as he proceeded on to pick projects like Titanic, Catch Me If You Can, Gangs of New York, and The Departed – projects that would go on to define his extraordinary career.

Tobey Maguire and Leonardo DiCaprio at an LA Lakers game in 2009.
On the other hand, Tobey Maguire, who also launched his career as a child actor in 1989 (the same year as Leo DiCaprio landed his first serious role) didn’t have a very comfortable transition into adulthood.

The young actor went on to win roles in projects such as Great Scott!, The Ice Storm, Pleasantville, and The Cider House Rules through the ’90s, before landing Sam Raimi’s Spider-Man in 2002.

However, the actor had to battle past addiction – something that most young artists succumb to as a counteragent to early exposure, wealth, and fame.

Tobey Maguire has been sober since the young age of 19 and announced in 2003 that he was “a recovering alcoholic.”.