Chairman of The Board

This may be taken as a man-crush but I have to say it anyway: Leonardo Dicaprio is a pimp.

Let's look, for a moment, at the way this guy was able to spend his twenties:

While Brad Pitt, Ben Affleck and the rest were being driven halfway to nervous breakdowns-- living in L.A., married to famous women, running around like fugitives in sunglasses and baseball hats, their names literally mangled (i.e., Brangelina, Tom-Cat...) by bottom feeding faux-journalists--Leo quietly took his Titanic money, moved to a mediteranean paradise to, instead, swim and bang supermodels in peace.

He does no interviews, is absent from premiers and nightclubs. He'll show up at the Oscars, but then only when nominated. He has found a way to, over-and-again, drop completely off the map for two years at a stretch while maintaining the star power of Johnny Depp and Tom Hanks combined. It seems the only reason he bothers with Hollywood at all is to star in the latest Spielberg or Scorccesse flick.



He was on Letterman a few years back, promoting The Aviator , and I noticed a vibe--a strange vibe. It was like it had been a really long time since he'd driven a car or paid for something with a five dollar bill. I got the feeling that he would be tickled to death with the notion of eating peanutbutter. When talented people are as famous for as long a sustained period as Leo has been famous, I think it's only natural for them to be, well...a little fucked up.
There may be some major chinks in Leo's armor that we don't know about. He might be an under-the-radar philanthropist or he might kidnap baby kittens and use them for target practice in his backyard. It'll all come out in due time. But Leo is thirty now and the way he's played Hollywood is something to be appreciated.