From the "would-have could-have might-have" department comes a look back at what DiCaprio’s career might have been. Since he’s already been in two of the year’s best movies in Shutter Island and Inception, I think it’s safe to assume that what it might have been is not as good.
But the website Shortlist got Leo to talk about the roles he’s turned down over the year’s, and since he’s Leo they’ve been big ones. According to Leo he met with Schumacher for Robin in Batman Forever. That role went to Chris O’Donnell who is presumably sleeping on the street somewhere right now. He was in talks to play Anakin in the Star Wars prequels and while you might think he’d have been better than Hayden Christensen, remember that Lucas has a talent for making great actors seem awful. Just look at what he did to Natalie Portman. They talked to him about playing Spider-Man before the part went to Tobey Maguire. Leo said no thanks to that one too.
I think it’s safe to say that DiCaprio has a knack for picking good projects. If he’s in it, it’s almost always good. Of those three only Spider-Man wasn’t an utter disaster, though I think Spidey might have been if Leo played Peter Parker. He’s a great actor, but he’s not a fit for the awkward, geeky, teenager role. Stick with the edgy, challenging, artistically satisfying stuff Leo; it’s working for you.
