Jared Feldman: Hello and its time for another edition of the Entertainment Bureau’s Chat Wrap. Jared Feldman here with Jay Sage. Today we’ll be dicussing an actor who’s career has been on a rollercoaster over the past twenty years, that would be Leonardo DiCaprio. He began as a young actor in What’s Eating Gilbert Grape before becoming king of the world in Titanic and recently the dream stealing Dom Cobb in Inception. Can you even guess where his career will go next Jay?

Jay Sage:  Well, next up is a Baz Lurhman interpretation of the classic American novel, The Great Gatsby, starring Leo as Gatsby along with Carey Mulligan and Tobey Maguire.  Luhrman is among my least favorite directors after Romeo + Juliet but I’ll still be compelled to check it out.  As for the near future, DiCaprio is similar to our Johnny Depp case study from last week.  He’s on the verge of not being able to pull of the boyish protagonist anymore.

Feldman: Luhrman directed DiCaprio in Romeo + Juliet, but I don’t see him taking as many liberties with the story. I believe that with the proper script The Great Gatsby should be an accurate representation of the source material. As for DiCaprio I never thought he’d amount to much after Titanic, but he managed to turn into a real actor with Catch Me If You Can and Gangs of New York. Those were his turning point films in 2002 when he morphed from cutesey teen hottie to legitimate actor. And yes I said cutesey teen hottie.

Sage:  I guess you could say that DiCaprio is one actor that benefitted from doing the opposite of Robert Downey Jr’s advice in Tropic Thunder with Gilbert Grape.  But on a serious note, I too am amazed by his evolution.  Watch Titanic again and you’ll see that he’s outclassed by everybody from Kate Winslet to Billy Zane, but he’s taken so many steps forward.  Even though he won the Best Actor Oscar for Blood Diamond, I think Catch Me If You Can has been his career pinnacle.  He and Tom Hanks play off of each other so well, and it’s as if the old star is handing the baton to the new one.

Feldman: Since that film he’s really sunk his teeth into every role since. He’s done The Departed, The Aviator, Revolutionary Road and Shutter Island to name a few. While they weren’t all great films, they featured roles that DiCaprio could take advantage of and display his versatility. He’s lucky he hasn’t been typecast in any particular way, allowing him to try a multitude of roles.

Sage:  What a fantastic career so far.  It’s an odd thing to say, but the one thing that’s really missing from DiCaprio’s resume is a memorable supporting role.  He’s really never been lower than second billing (and even that’s rare).  The mark of a great actor is the ability to appear on screen for around 15 minutes and still steal the show.  Sort of like Anthony Hopkins in Silence of the Lambs.

Feldman: He was a part of a large cast in The Departed though he was the first or second leading man in that. He will have to share the screen in the upcoming Django Unchained. The new Quentin Tarantino film features DiCaprio as a southern plantation owner who Jamie Foxx’s character Django seeks vengeance from. Leo will have a good deal of screen time, but at least he’ll be the villain and not the protagonist.

Sage:  That will be a nice shift in his paradigm as an actor.  So, it’s difficult to name an important actor or actress of our time that Leo hasn’t yet worked with.  He’s been opposite of Tom Hanks, Matt Damon, Jack Nicholson, Rachel Weisz, Cate Blanchett and Kate Winslet just to name a few.  Who’s another actor that you’d love to see him share the screen with one of these days?

Feldman: I’d love to see him go toe to toe with Edward Norton in an antagonistic role, and a pairing with Denzel Washington could be epic. Leo is talented enough to play any role, but usually he is by far the most accomplished actor in any particular film. To see him play off another equally talented actor would immediately make the film a Best Picture contender.

Sage:  Edward Norton was actually going to be my answer too.  An impressive give and take that I was forgetting was between Leo and Daniel Day Lewis in Gangs of New York.  So to answer my own question, maybe an up and comer in Jeremy Renner?  He’s sputtered a little since the success of The Hurt Locker.

Feldman: Renner’s taken his success from the Hurt Locker and parlayed in into a few more popcorn roles like in Mission Impossible 4 and the upcoming Bourne Legacy. He’s very talented playing the armed forces/secret agent type character but hasn’t really gotten any other types of roles. Pairing him with Leo DiCaprio would be a very interesting film.

Sage:  Or how about Meryl Streep?  That would certainly be interesting.  Here’s another question…does Leo have a superhero movie in him or do you suppose he’s intentionally avoided that trend for fear of not being taken seriously?

Feldman: Luckily there aren’t really any major ones left to portray in film, unless he takes over Batman from Christian Bale. I think over the past decade DiCaprio has intentionally opted for only “quality films” even if a big payday was possible. He can pick and choose the roles he wants, and I wouldn’t be surprised if he opted for producing and directing himself in the near future. A role that would be good for him would be along the same lines of The Departed, and Mystic River. A gritty crime drama set in the slums of a metropolis, facing a deranged killer. Or being the deranged killer himself.

Sage:  Maybe we should just give in and turn this into a full-blown fan fiction piece. We’ll get back to all of you on that.  ‘Til then, a promising career that has now last a couple decades still seems to have a lot in store for it.  If there’s nothing else, that will exhaust another Chat Wrap here on The Entertainment Bureau.  Thanks for reading and be sure to check in soon for more on All Things Entertaining.

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