’s not unusual for prettyboy actors to try and ugly themselves up for credibility. Brad Pitt chipped a tooth on purpose for Fight Club. Jared Leto gained a bunch of weight for Chapter 27. Marlon Brando became a grotesque slob for every role after the mid-70s. I’m not pretty, but I can imagine the frustration in not being taken seriously because of your good looks (although since they got you where you are in the first place maybe you shouldn’t complain so much. I’m sure that there may be some guy out there who is ten times the actor Brad Pitt is, but his giant schnozz and asymmetrical eyes have kept him in Cleveland-area dinner theater).

Leonardo DiCaprio has to deal with this problem times ten. Not only is he very pretty, he’s got a baby face. At 32 (just a year younger than me!) he could easily pass for 21. Which he’s going to feel good about in fifteen years, but right now it’s probably driving him nuts. And the whole situation is made worse by the fact that we all remember him from his teenybopper days.

While Leo doesn’t seem to be interested in ritual Oscar-baiting self-mutilation, he has been turning his attention to darker characters, many of whom are denoted as dark by the sparse tufts of hair growing out of his chin. This year he’s done two of them – The Departed’s Billy Costigan is really a good guy playing bad, but he’s not sure how much good guy is left in there. Next Friday he’ll be hitting multiplexes in Blood Diamond as Danny Archer, an amoral smuggler and arms dealer who traffics in conflict diamonds, which are, according to Wikipedia, “mined in a war zone and sold, usually clandestinely, in order to finance an insurgent or invading army’s war efforts.”

The problem with these roles is that they don’t take the time to reference Leo’s obvious looks. This is especially annoying in Blood Diamond (a film that did not need any more annoying, distracting or goofy elements), where DiCaprio looks more than a little silly running around with a bunch of very manly soldiers of fortune. Danny Archer is one of those really rough and tumble characters – a hard drinking, smoking killing, but that’s rarely reflected in Leo’s face or body. There’s a scene where he is just out of the shower and he’s got a sleek swimmer’s body, completely hairless. I couldn’t decide if Leo waxes or if he just is mostly hairless (looking at his beard, I suspect the answer is hairless), but I had a hard time believing that his physique belonged to the character he was playing.

While I wish that there had been more mention of his boyishness in The Departed, it almost seems to work for him. Costigan is full of fury, and you can imagine it comes from being a scrawny kid who got picked on. He’s a guy who is always proving himself, and because he looks like the teenaged gopher when running around with Jack Nicholson’s Irish mob, you’re reminded why he has to be so fierce. In a lot of ways Leo is playing a Joe Pesci sort of role (he even has a Pesci-style beatdown sequence), where the little guy has to be twice the psychopath to compensate.

I’ve interviewed Leo at a roundtable once, for Catch Me If You Can, and been in two press conferences for The Departed, and I’ll tell you that he’s a fairly serious fellow. He comes across as intense, if not a little humorless. At the press conference for The Departed he kept playing the straight man to Matt Damon, who had a joke for every question. I feel like that intensity, that seriousness, is what’s getting in his way right now. He’s taking roles that are mirroring that intensity, but what Leo needs to do is take a role that’s about how young and good looking he is. He needs to do something more in line with Catch Me If You Can (or to some extent Gangs of New York), where his looks were perfect for his character. Of course he wants to do something more “serious” than that, but there must be a baby-faced killer he can play or something.

DiCaprio’s a hell of an actor – I’ve been defending him since What’s Eating Gilbert Grape (at the time I worked with retarded kids and I though DiCaprio, who I didn’t know from his TV work, really was retarded). And I’ll still defend him now – despite the fact that Blood Diamond is ultimately a cheesy piece of junk, and despite the fact that I don’t physically buy Leo as Danny Archer, I think he had the psychological aspects of the character down. But he needs to embrace the features he was born with and figure out a way to make them work for him in the kinds of roles he wants to play.

Or if that fails, maybe he can get a bunch of follicles transplanted to his face so he can grow a decent beard.