Leonardo DiCaprio and Tobey Maguire have been friends for decades after meeting while auditioning for the same role.

Leonardo DiCaprio has spent decades working in the film industry, and throughout these decades he has also made several friends and connections. However, one of these relationships that has stood out the most has been his years-long friendship with the Spider-Man actor Tobey Maguire. The duo reportedly first met while auditioning for the same role, and this being in the same line of work, they would continue to be the other’s competition.

Leonardo DiCaprio and Tobey Maguire
Something similar happened when they auditioned for the 1993 film The Boy’s Life. However, DiCaprio beat his best friend and landed the lead role after he screamed at the Hollywood star Robert De Niro.

Leonardo DiCaprio’s Outburst Landed Him His First Major Role
After making brief appearances in movies and TV shows, Leonardo DiCaprio went in to audition for the 1993 movie The Boy’s Life. This would end up being another movie role that he and his friend Tobey Maguire competed for. However, he was not the only one.

Leonardo DiCaprio and Tobey Maguire in their teenage years
Around 400 child actors auditioned for the part, and the Titanic star did not want to lose the opportunity to star alongside Robert De Niro. During an interview with Deadline, he shared that he decided to do something “memorable” that would eventually get him the offer.

“I went in, and they were doing the mustard jar sequence,” he said before adding, “and [De Niro]’s like, ‘Is it empty, is it empty?” After which, he took the chair and threw it down and screamed at him, “No, it’s not empty.” DiCaprio first assumed that it might backfire and he would never get the opportunity.

“I was like, ‘Holy s**t, I blew it. I blew this. I blew this whole opportunity,” he recalled. However, contrary to his assumption, the Oscar winner was impressed with his unconventional move. DiCaprio eventually landed the role, beating hundreds of child actors, including his friend Tobey Maguire.

Tobey Maguire Believed Leonardo DiCaprio Was Not Serious About the Audition
While Tobey Maguire failed to land the lead role in the 1993 film The Boy’s Life, he was cast in a minor role in the movie, which went on to be his first credited appearance in a feature film. The actor later revealed that he was sure that his friend would not land Tobias’ part in the film.

Tobey Maguire and Leonardo DiCaprio
During an interview, he recalled that his behavior during the audition gave him the impression that he was not taking it seriously and would probably lose the part. “He was doing karate kicks in the hallway. He wasn’t serious at all,” he said, as per Vanity Fair.

The actor further shared that he was ignorant about one of the biggest Hollywood stars Robert De Niro. When he asked him about the actor, he said, “De Niro . . . wasn’t he in Cape Fear?” However, these personality traits went on to be one of the reasons the Inception star eventually scored the role.

Leonardo DiCaprio with Robert De Niro during the 77th annual Golden Globe Awards
“My ignorance, as Tobey says, was a kind of advantage,” he told Vanity Fair. He has also shared that he learned a lot working on the movie and its director Michael Caton Jones. DiCaprio and Maguire have also been friends and have worked in several movies together as well.