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Photos of Leonardo DiCaprio Looking Like Frank Sinatra on the Cover of Esquire Magazine 2010-02-11 12:30:06

Leo Dishes His Top Ten Life Lessons to Esquire

Handsome Leonardo DiCaprio is looking cool as ever, with a glowing tan, slicked back hair and drink in hand on the March cover of Esquire. The actor's next film Shutter Island finally opens next week so he's reflecting on his impressive career and the life lessons he's learned along the way. Most of you think Leo would be the best choice to play Frank Sinatra in the upcoming Martin Scorsese biopic and judging by these photos he looks like he's already practicing for the part. Here's more:

  • Leo on River Phoenix: "When I was eighteen, River Phoenix was far and away my hero. Think of all those early great performances — My Own Private Idaho. Stand by Me. I always wanted to meet him. One night, I was at this Halloween party, and he passed me. He was beyond pale — he looked white. Before I got a chance to say hello, he was gone, driving off to the Viper Room, where he fell over and died. That's a lesson."
  • His earliest memories on stage: "The earliest memories I have are jumping up onstage before concerts in downtown L. A. and trying to get on the mic and break-dance, or do imitations of my mother's friends or my father's friends, or be a comic in class. I was the most insane child you can imagine, pretty intolerable to be around. High-octane energy all the time, never wanting to focus on schoolwork."
  • On what drives him to act: "Probably the only thing I knew with complete clarity was that I wanted to be an actor. But there was a lot of rejection early on, and so it never felt like, Hey, I've got something here. There was always an element of me that needed to prove something to myself. It's something I don't want to get rid of, because it's what drives me. I'm never settled and I'm never satisfied."

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AmalieDanielle AmalieDanielle 7 years
i adore him since forever.can't wait for Shutter Island. :)
AmalieDanielle AmalieDanielle 7 years
i adore him since forever. can't wait for Shutter Island. :)
lovekailua lovekailua 7 years
It makes me feel so damn old to see Leo looking so....well, old. haha. Still sexy though! Love that Leo. I always see his movies.
lolamaria lolamaria 7 years
Why is it when people mention River Phoenix, they have to bring up his death? We get it, he died. Why couldnt he have said that he was his hero and leave it at that? I also dont think he has aged well.
slikkback slikkback 7 years
boy can act, I'm never dissappointed with his movies =D
ffrench ffrench 7 years
:drool:
ffrench ffrench 7 years
:drool:
Pampire Pampire 7 years
I've always thought he was kind of cute not all that, but I have to admit that he looks sexy in that second picture, I think it's the eyes.
THoMaS_CRoWN THoMaS_CRoWN 7 years
Very classy man..Nice interview, he's a rare gem in Hollywood..
betty-kraker betty-kraker 7 years
i think he has always been hot
mrsld mrsld 7 years
Shenan- When was he not hot?These shots of him are amazing! :drool:
mrsld mrsld 7 years
Shenan- When was he not hot? These shots of him are amazing! :drool:
babaloo babaloo 7 years
One of the great, if not greatest, actor of his generation. I'll pretty much see whatever he is in. Love his movies.
TammyO TammyO 7 years
When did he get so weather beaten and steamy looking?? Remember when he was all baby faced Jack from Titanic? Geesh I'm older than he is and he looks like a grizzled dude in these photos.
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