Tobey Maguire Doubted Leonardo DiCaprio Had a Chance Getting Cast in His Breakthrough Film

Leonardo DiCaprio has been good friends with Spider-Man megastar Tobey Maguire since their childhood days. Although they’ve greatly supported one another, Maguire thought DiCaprio might not have taken his first real film opportunity seriously enough.

Tobey Maguire and Leonardo DiCaprio have been friends for decades

DiCaprio and Maguire’s friendship might be one of the longest in Hollywood. The two met while they were extremely young up and coming actors looking for their breakthrough. Maguire left a significant impression on DiCaprio, and the two bonded from there.

“After I met Tobey at an audition, I felt like I wanted this guy to be my friend,” DiCaprio once recalled in an interview with The Associated Press. “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?'”

Since then, the two have had somewhat comparable careers. They’ve both become blockbuster superstars in their own right. DiCaprio officially achieved his A-list status with Titanic, while Maguire reached a new level in his career with Sam Raimi’s Spider-Man trilogy. Still, the two have remained close, and DiCaprio shared they maintain constant communication with each other.

“Every project we do, we talk about,” DiCaprio said. “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.”

Tobey Maguire didn’t think Leonardo DiCaprio would end up starring alongside Robert De Niro in ‘This Boy’s Life’

This Boy’s Life was one of DiCaprio’s first notable film roles. The movie was a 1993 feature based on the memoir of Tobias Wolff. At the time, it was a crowning achievement for DiCaprio, who beat out hundreds of aspiring kid actors to star in the film. One of those actors was Tobey Maguire himself.

But initially, Maguire didn’t think DiCaprio would end up with the role. If only because his friend at the time didn’t seem to be focused on the part.

“He was doing karate kicks in the hallway. He wasn’t serious at all,” Maguire once said in an interview with Vanity Fair. “Leo says, ‘De Niro . . . wasn’t he in Cape Fear? I said, ‘Are you f***ing kidding me, dude?'”

But DiCaprio felt that not being too familiar with De Niro was what helped him score the role.

“My ignorance, as Tobey says, was a kind of advantage,” DiCaprio said. “Anyway, I stood up in front of De Niro really forcefully and I pointed at his face and screamed one of the lines. Then I sat there and waited for some kind of reaction. I remember De Niro had this smirk on his face, like, obviously [he knew] this kid wanted to come in here and show him that he had guts. Everyone started laughing and I said, ‘What? What is it?’ And, well, the cool thing is that I obviously showed him something.”

Leonardo DiCaprio initially thought he bombed his audition with Robert De Niro after improvising

In hindsight, DiCaprio’s stunt may have been a good idea. But in the moment, the Oscar-winner immediately had his doubts after going off script. The instant reaction DiCaprio’s improvising caused wasn’t the type he expected.

“I remember there was a mustard jar scene, and he had to jam a mustard jar in my eye repeatedly, it was an abuse scene,” DiCaprio said in an interview with SAG. “And the script sort of didn’t call for it, but I got up and he said, ‘Is it empty? Is it empty?’ And I got up and I screamed, ‘No!’ … I screamed in his face, and I sat there with my head looking like a red tomato and everyone started laughing at me. … And I sat there frozen, just thinking, ‘Oh my god, I just screwed this entire opportunity up.'”

But De Niro reassured his co-star that his act might have worked.

“And then Bob, in traditional De Niro fashion, kind of just looked at me and went, ‘It’s good,'” DiCaprio recalled.