Every Movie Tobey Maguire And Leonardo DiCaprio Have Done Together

Leonardo DiCaprio is one of the most sought-after and well-respected actors in Hollywood, thanks in part to the blockbuster success of "Titanic," and his Academy Award win for best actor for his role in "The Revenant" in 2016 (via Esquire). The early 2000s and Sam Raimi's "Spider-Man" movies made Tobey Maguire a household name, but his performances in "The Cider House Rules," "Wonder Boys," and "Seabiscuit" put him in the award season conversation (via IMDb). Maguire and DiCaprio are two of the most well-known actors in the world due to their respective acting careers, but many would be surprised to learn that the two men have been friends for over 30 years.

In a 2013 interview with Esquire, DiCaprio shared that the two became friends when he was only 12 years old. DiCaprio, Maguire, and a few other actors used to go on the same auditions and would frequently run into each other. DiCaprio was determined to make Maguire his friend, and his efforts eventually paid off. They have since established one of the greatest Hollywood friendships in recent years. 

Their friendship may have lasted this long because, while auditioning as children, they made a pact to help each other get roles (via YouTube). This pact has carried DiCaprio and Maguire through three decades, and it has resulted in movies where they were able to act opposite one another as well.

This Boy's Life

Leonardo DiCaprio and Tobey Maguire first appeared on film together in "This Boy's Life." The film was based on Tobias Wolff's memoir about his life and relationship with his abusive stepfather. Michael Caton-Jones directed the film, and it stars DiCaprio as a character (ironically) named Toby, with Robert De Niro starring as his stepfather Dwight. The cast also included Eliza Dushku and Ellen Barkin. Maguire had a small role as Toby's friend Chuck (via IMDb). "This Boy's Life" premiered in 1993 and was one of DiCaprio's first major film roles.

In a conversation with SAG-AFTRA in 2014, DiCaprio shared that he and Maguire made the final five auditioning for the role of Toby in the film (via YouTube). To stand out, DiCaprio improvised a moment that resulted in everyone laughing, but De Niro advocated for him to get the part. DiCaprio then suggested Maguire for the role of Chuck.

According to DiCaprio, "This Boy's Life" not only helped cement his bond with Maguire, but it helped him hone his acting skills and develop a lifelong bond with De Niro (per YouTube). DiCaprio and De Niro later collaborated again in "Marvin's Room" (via IMDb).

The Great Gatsby

Leonardo DiCaprio took on the role of Roaring '20s poster boy Jay Gatsby in "The Great Gatsby," directed by Baz Luhrmann. This 2013 adaptation of F. Scott Fitzgerald's beloved book also featured Tobey Maguire as Jay's friend and story narrator Nick Carraway (per Warner Bros.). The film marked the reunion of Luhrmann and DiCaprio, who previously worked together on "Romeo + Juliet" in 1996 (via IMDb). The film also marked DiCaprio and Maguire's film reunion.

In an Esquire interview, it was reported that DiCaprio personally called Maguire and asked him if he wanted to play the part of Nick Carraway. This makes sense for Maguire to be DiCaprio's first choice given their long history, as well as Gatsby's close friendship with Carraway in the book. The film was a box office success, grossing over $350 million worldwide. "The Great Gatsby" also went on to win two Academy Awards: one for best production design and another for best costume design (via The Hollywood Reporter).

Don's Plum

"Don's Plum" filmed in 1996 at the peak of Leonardo DiCaprio's rising fame. It began as a collaboration among friends that turned into the most controversial aspect of DiCaprio's friendship with Tobey Maguire. According to a New York Post docuseries, Maguire and DiCaprio agreed to be in "Don's Plum" as a fun thing to do with their group of friends, but it resulted in lawsuits and the film's banning in the USA and Canada (via YouTube).

Maguire and DiCaprio became the main faces of an infamous '90s young-Hollywood group dubbed the P***y Posse. A Complex article detailed their questionable behavior, which included wild fights, hooking up with various women, clubbing, and using their fame whenever possible. "Don's Plum" depicted a similar group of young men behaving in similar ways, and it featured many of the known members of the P***y Posse. Much of the film was improvised — according to the New York Post docuseries, this made people worry that DiCaprio and Maguire would be associated with the bad behavior in the film, which would then negatively impact their real personas.

All the anxiety from Maguire and DiCaprio surrounding the film led to an agreement that it would not be legally distributed in the USA and Canada. The men in the P***y Posse have grown up, but their friendships seem to still be going strong, especially between Maguire and DiCaprio. They may be celebs that many didn't know were besties, but their relationship remains one of Hollywood's strongest.