leonardo dicaprio & jay-z*It’s not surprising that Leonardo DiCaprio hooked “The Great Gatsby” director Baz Luhrmann up with Jay Z, who not only supplied music for the film but also became an Executive Producer.

What is surprising is that at the junket for “Gatsby,”  an MTV online writer said he was surprised to find DiCaprio a fan of hip hop.  DiCaprio has been a fan of Hip Hop for many years. At one time a good friend of A Tribe Called Quest’s  Q-Tip, he interviewed him for the 2008 April edition of Interview Magazine.

In 1998 Q-Tip was embroiled in a scuffle with a photographer when he tried to take a picture of DiCaprio at a club where they were partying. That same year there were rumors that DiCaprio was caught up in a “romantic triangle” with the daughter of Quincy Jones, Kidada, who was reportedly dating Puff Daddy. DiCaprio’s good friend Tobey Maguire was engaged to Kidada’s sister, Rashida—the two dated for more than three years].

In this the fifth film edition of the F. Scott Fitzgerald classic, “The Great Gatsby,” Luhrmann presents a visibly captivating version with arresting performances that would make Fitzgerald proud. The music is incredible and hip hop fits perfectly into this 1920’s drama. It is not surprising that DiCaprio was tapped to portray Gatsby. He is one of Hollywood’s finest actors, yet most underrated. Oscar has ignored him on a number of occasions. In 2008 when The Film Strip interviewed DiCaprio and Kate Winslet together for “Revolutionary Road,” I asked Winslet if he sometimes surprised her with his performances because his was one of the best I had seen all year? “I think that he’s nicer than he was, given if that’s possible,” she laughed as DiCaprio looked on smiling.

“He’s funnier than he was even if that’s possible and he’s a better actor than he was even if that’s possible,” she continued. “Quite honestly, playing Frank and April Wheeler there was a surprise everyday. I just loved so much playing some of the difficult scenes with Leo knowing that because of the trust that we have as two people having known each other for so long that there were just no boundaries. That was a real gift to have as two actors playing these parts and to be able to do off camera dialogue for him and to have to stop myself from crying because I was seeing someone for whom I have so much respect as an actor. I saw him do things that I have never seen him do before; morph his face into positions that I’ve never seen him morph his face into as an actor and as a person. There were many moments like that pretty much every single day.” Those were my sentiments exactly and not only did he win an Oscar for that performance, but he wasn’t even nominated! DiCaprio proved his skills way back in 1993 when he played the mentally challenged young brother of Johnny Depp in “What’s Eating Gilbert Grape.”

His latest role brought him back to New York but this time to the Plaza Hotel where many Jay Gatsby parties were held. The Film Strip asked DiCaprio why is it that here we are in the 21st century yet we continue to see history repeat itself? Expecting a terse response like, “It’s because we never learn from our mistakes,” DiCaprio gave a pensive and introspective answer—a proclivity I’ve found him prone to have over the course of interviews that appeared here.

“Baz talks about it a lot but in a way, this book predicted the great crash in the early 1930’s in America,” DiCaprio explained. “It’s a book that talks about the great opulence and wealth in America in that time period and the idea that the future is endless and we can keep consuming and living the way we do without any consequences. It is timeless in a sense that it’s an 80-year cycle. We encountered it again in our modern era and it’s something that we keep doing. It’s not an American novel in that regard, it’s something that’s happening worldwide. Fitzgerald was very much commenting on society and human nature and the great pursuit of wealth.”

Reluctant to go the “Great Gatsby” route once more, DiCaprio read the book again.

“Certainly, the Gatsby that I remember reading when I was 15 years old in junior high school was far different from the Gatsby I read as an adult,” he says. “What I remember from my years in junior high was this hopeless romantic who 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 re-read it as an adult, it was incredibly fascinating. It is one of those novels that is talked about a hundred years later for a reason. It’s nuanced, it’s existential and here at the center of this movie is this man that is incredibly hollow and searching for some sort of meaning in his life. He has attached himself to this relic known as Daisy. She’s a mirage.

“I was struck by the sadness in him for the first time and I looked at him really differently. Nick (Maguire) is the only one who truly sees what’s going on, a man desperately clinging on to an image. He’s a character that has created himself according to his own imagination and dreams. He’s lifted himself from his own bootstraps as a poor youth in the Midwest and created this image that is this Great Gatsby. It’s a truly American story in that regard. I think we can all relate to the dreamer in Gatsby. Each one of us gets excited by the prospect of someone that has that much ambition.”

Tobey Maguire’s heartfelt portrayal as Nick Carraway is, for the most part, art imitating life.

“I think Leo and I have a trusting and close friendship,” Maguire confers. “So just the kind of comfortable, open dialogue that we had on the work and process contributed to what we did. In regards to the actual texture and chemistry of the relationship, it’s harder for me to judge what contributed to that but I’m sure that that had an effect there. I definitely have an affection for Leo so it’s easy for me to have affection for Gatsby as Nick as well.”

DiCaprio agrees.

“For me, this is American Shakespeare,” he says. “This is one of the most celebrated novels of all time so to venture into a project of this magnitude took a core unit of trust for me to feel comfortable and know that somebody that I knew for 20 years and Baz Luhrmann was involved. To know that Tobey was immediately involved from the onset was incredibly comforting. We’re always extremely honest with each other and for me, I don’t know if this project would have happened if we didn’t have that sort of relationship because we needed those checks and balances.”

Baz Luhrmann had no qualms about infusing hip hop into the film. He says Gatsby’s 20s was set in the jazz age and that hip hop best qualifies most as the jazz of the 21st century. With that in mind, DiCaprio was more than happy to hook him up with his friend, Jay Z.

Syndicated columnist Marie Moore reports on film and TV from her New York City base. Contact her at [email protected]