Leonardo DiCaprio & Tobey Maguire on ‘Gatsby’ Chemistry and Real-Life Friendship

05.2.2013 | By |

*Updated January 2026

Leonardo DiCaprio stars in Baz Luhrmann’s adaptation of The Great Gatsby. In the film, the actor plays Jay Gatsby, a fabulous party-giving man with a mysterious past. He comes out of nowhere to buy a mansion on Long Island, sitting directly across the bay from his one true obsession, the now-married Daisy Buchanan.

Every night, Gatsby stands out on his dock and tries to reach out for a green light that comes from Daisy’s house, but when Nick Carraway (Tobey Maguire), cousin of Daisy, moves to a small bungalow next door, Gatsby ceases the opportunity to get closer to his golden girl in a plot that ultimately leads to… enough for now.

This week we had the opportunity to speak with DiCaprio, The Great Gatsby co-star Tobey Maguire, and director Baz Luhrmann. Here is what they had to say.

(This interview was edited for clarity).

ShowBizCafe (SBC): Did you identify as someone who didn’t grow up very wealthy? Did you identify with this hunger to want more?

Leonardo DiCaprio (LD): I think everyone has some sort of connection to Gatsby. He is a character that has created himself according to his own imagination. He lifted himself from his own bootstraps as a poor youth in the Midwest and created this image that is the great Gatsby.

It’s a truly American story in that regard. Here is this emerging democracy that is America in the 1920s and he wants to emulate the Rockefeller of that time period. Of course, he creates his wealth in the underworld.

But this is the new land that is America and it was a very exciting time. I think we can all relate to that dreamer in Gatsby. Each one of us gets excited by the prospect of someone that has that much ambition.

Reimagining a Literary Classic

SBC: Gatsby is somebody who has reinvented himself. Did that plug in at all in how you saw Jay Gatsby and what he was doing?

LD: Certainly, the Gatsby that I remember reading when I was 15 years old in junior high school was far different than the Gatsby that I read as an adult. What I remember from my years in junior high was this hopeless romantic. He was solely in love with this one woman and created this great amount of wealth to be able to respectfully hold her hand.

But then to reread it as an adult, it was incredibly fascinating. It is one of those novels that is still talked about nearly 100 years later because it’s incredibly nuanced and existential. Here at the center of this movie is this man who is incredibly hollow.

He is searching for some sort of meaning in his life and has attached himself to this relic known as Daisy. She’s a mirage.

[As an adult] I was struck by the sadness in him for the first time and I looked at him completely differently. I looked at him as somebody that was very hollow and searching for some sort of meaning. Nick is the only one that truly sees what is going on in reality: here is this man that’s desperately holding on to this image.

One very telling sequence that we talked a lot about, and for me was a very important one from the book, was after this caravansary that he’s created known as Gatsby’s castle. He created it to lure Daisy in. Nick notices that he is holding her yet he is still staring out into the green light.

He finally got her in his arms but is still searching for this thing that’s going to complete him. That was the Gatsby that I was incredibly excited about playing as an actor. As I got older it took on a new meaning and that’s what is so incredible about this novel.

Everyone who reads it has their own interpretation of who these characters are. That’s what is very difficult about making a movie about it. Everyone has their own personal attachment to the book and they feel like they know these characters on a very intimate level.

Tobey Maguire and Leonardo DiCaprio Chemistry

SBC: Tobey and Leo, you guys have a lot of great chemistry on screen, a great friendship and that really came across. Did the friendship you already had translate into the characters?

Tobey Maguire: I think that Leo and I have a very trusting and close friendship. Just the comfortable open dialogue we had in terms of the work in process contributed to what we did. In regards to the actual chemistry of the relationship, it’s harder for me to judge what contributed to that but I’m sure [the friendship] had an effect.

I think the Nick and Gatsby relationship is such an interesting relationship to explore. From my point of view, obviously, I’m looking through the eyes of Nick. I am searching through the book as Nick and looking at his relationship to Gatsby in particular.

The way we made the movie and the way the book is written, Nick is looking back over his experiences. So there are both the experiences in real-time as he lived them and Nick’s relationship to the latter.

Looking back on who Gatsby was to him personally and as an idea, I think inspires Nick to go off into his own future. Specifically, having an understanding that Gatsby had an agenda for Nick, but ultimately unfolded into a real friendship. Perhaps it was Gatsby’s only friendship.

I think [this] was very meaningful to Nick. I definitely have an affection for Leo so it’s easy for me to have an affection for Gatsby as Nick.

LD: For me, this is like American Shakespeare. This is one of the most celebrated novels of all time. To venture into a project of this magnitude it sort of took a core unit of trust for me to feel comfortable.

To know that Baz Luhrmann was involved and Tobey was immediately involved in that process from the onset was incredibly comforting. [Tobey Maguire and I] are always extremely honest with each other. To me, I don’t know if this project would have happened if we hadn’t had that relationship.

It needed that. We needed those checks and balances and we needed to have a contract with each other to continue to be honest with one another.

Baz Luhrmann: Can I add a little thing to that? Because I think these two gentlemen cannot say this but it’s a little anecdote from our first day of shooting in the flower scene. We were all very nervous because what we touched upon is that we felt we were carrying a very heavy chalice and great responsibility.

There was written dialogue in the scene. It’s when Gatsby is waiting with Nick for Daisy to arrive. I put a locked camera as a wide shot and said: “You’re just waiting for Daisy but let’s not do the scene, just improvise.”

That moment I think is one of the purest and most connected moments of the whole film. It completely came from a depth of relationship that existed before we began rehearsals. It’s funny because it was this first thing we ever shot and for me, it’s one of the most truthful and wonderful moments in the film.

History Repeats Itself

SBC: Seemingly the more that things change the more that they remain the same. Leo, Tobey, why do you think that history repeats itself?

LD: Baz talks about it a lot, but in a lot of ways this book predicted the great crash of the early 1930s in America. It’s a book that talks about the great opulence and wealth in America during that time period. It covers the idea that the future is endless and we can keep consuming and living the way we do without any consequences.

[The book] is timeless in the way that this is an 80-year cycle. We encounter this again in our modern era and it is something that we keep doing. It’s not just an American novel in that regard.

It is something that is happening worldwide. Fitzgerald is commenting on society and human nature and the great pursuit of wealth. It’s a timeless novel in that regard.


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