I'm a big fan of Leonardo DiCaprio. Of course I am, I'm a girl in her 20s who grew up on Leo, and have come to admire him all the more as his career has evolved beyond teen heart throb to Oscar nominated actor.
Why then would I question his luck? My concern for the golden boy comes less for the actor and more for his characters, who are almost all terribly unlucky. I won't mention them all, but by and large, his roles are that of tortured men who often either die themselves or suffer the death of a loved one (usually a lover). If they survive, it is to a life of hardship and torment. So here's my question to contemplate as you read on: is it the actor who chooses the role or the role that chooses the actor?
I'll start with What's Eating Gilbert Grape, a great performance by our leading man, but clearly a character with lots of problems, from the obvious mental handicap to his disinterested brother to his obese house-bound mother (who dies).
On to Basketball Diaries. If you've seen this movie, it's pretty self explanatory why it's on my list. A growing drug addiction comes between him and his goal of basketball greatness, leading him to do truly horrible things to sate his appetite for heroin. No, he doesn't die in this one, but his dreams do.
Oh, Romeo + Juliet, how you shaped my young romantic visions. This is where Leo and I began the love affair we've had in my mind all these years. He was the perfect man to myself and many other young impressionable girls, all of whom felt his angst, which begins as apathy seeking something more, grows to an infatuation with exactly the wrong girl, the forbidden nature of the love adding all the more to its potency, and then the inevitable denouement as first she appears to die, then he dies to be with her, she awakes, finds him dead, and shoots herself beside him. We all know the story, it's an age old tragedy, and his emotive powers brought it home for us.
And then his next tragic love story, Titanic. Sure, plenty of people deride a story that begins with a girl trying to kill herself by jumping off the Titanic pre-iceberg. But I think everyone took a guilty pleasure in Celine Dion after that movie (which I think I showed restraint in only attending in the theater 3 times). Jack, the starving artist who wins tickets onto the largest boat in the world, becomes intrigued by a rich girl with ennui, and has a short lives love affair that ends when they can't both fit on a floating door and his chivalry allows him to freeze to death. Plenty of people got mad at Rose (the adorable Kate Winslet) for allowing him to perish in the frigid North Atlantic, but it's part of his character to save her above himself, and part of why we all loved him so. Alas, once more, he died for love.
And then Aviator. A study in madness via Howard Hughes. I don't think I really need to say much of anything about why this role was profoundly disturbing. Sure, he dated Katharine Hepburn for a while, and was able to fly the Spruce Goose, at least a little ways. But the layers of madness that descend on him thereafter, the lines of jars of urine, the fingernails. Even when he attempts to clean up and pull himself together, the paranoia and compulsions continue to the very end. I think this was the movie that really introduced Leo to us as a serious actor capable of handling complicated and confounding characters.
Thereafter, his movies are all powerful, evocative, and riddled with death and deception. The Departed, a great film, where our hero is bullied into spying on the bad guys from inside, and ultimately killed (though he does get to sleep with the real bad guy (Matt Damon)'s fiancee first). But I believed him as a Bostonian and as a guy coming out of a rough past, trying to make good. However, I think my favorite character in the movie was Mark Walberg's Dignam, I mean what a prick, but eventually, the only one to see through what was really happening and get the last word (or bullet).
In Blood Diamond he's a mercenary (Danny Archer), greedy and looking for his ticket out of Africa and its constant warfare, regardless of who falls by the wayside in his pursuit. It is in this he falls in with Solomon (Djimon Hounsou), a man ripped from his family and desperate to get back to them, as well as Maddy (Jennifer Connelly), a reporter with some useful connections. Together, they fight their way to find a large diamond, Solomon's family, and a way out of Africa. Alas, Archer grows a conscience along the way, and an attachment to his fellow travelers, which leads him to sacrifice himself for their welfare. Once again, our hero dies in this one.
Revolutionary Road (based on a wonderful book by Richard Yates) places Leo once again opposite Titanic costar Kate Winslet in a story of young dreams and ambitions sliding seamlessly into the drudgery of everyday suburban life. The couple who were so hopeful for adventures and opportunities settled for a little cottage in a quiet community, children, and the 50's life of a housewife and bored, unfaithful business man. They decide to make a change, to do something about the monotony of their lives, to move to Paris and just see what happens. Alas, even as they formulate their plans and regain hope, Kate's character becomes pregnant again, and they must face that the financial realities of another baby won't allow them to make this move. The tension of options not legally available in this age flood them until Kate's character finds she must take things into her own hands or drown. Leo is then left to discover his wife bleeding to death, his baby gone, and himself left alone to raise his two remaining children.
Lest we think this is the worst that could happen to one of his characters, along came Shutter Island. I must admit, once I made my way fully through this movie, I sympathized with old Teddy Daniels (Leo) in wanting to retreat into a world of his own imaginings rather than face reality. Yes, I am giving it all away, I apologize, but I did warn you. Throughout, I enjoyed the great mindfuck of it. By the time he saw rats covering the cliff side, I was starting to wonder just what was up with him (but maybe they had slipped him drugs). Not until he crumbles the plastic gun in his hand after trying to shoot the doctor with it was I convinced. And then the horrible memory returns to him, his insane wife drowning all three of their children, still not seeing that she had done anything wrong, and him finding no choice but to kill her, as much as he loved her. Yes, I think this one takes the cake as his most tortured and destroyed character. And to date, the best mindfuck film he'd done.
That is, until Inception. I adored this movie. This kind of sci-fi trippy ride is exactly the kind of movie I enjoy. Sliding through other peoples dreams in layer upon layer of non-reality, never quite sure you are really awake, in the real world at all. And we are set up with a man who has been so scarred by previous experiences in the dreamscape of his existence that he can't even trust himself to design the dream worlds anymore. He is haunted, literally, by the memory of his dead wife, who appears to make trouble for him, to punish him for letting her die alone. In the midst of all of this emotional drama, a gang of dream bandits must plant an idea in a man's mind in such a way that it can grow naturally as though spawned in his own mind. This involves three layers deep of dream within a dream, the danger of losing themselves in the limbo of the subconscious mind, and precise timing in order to complete the job before waking. The concept is fabulously intriguing, the actors all contribute (Ellen Page and Joseph Gordon-Levitt notably), and the film is able to leave you not quite sure what's real (to the point of sparking incredible online debate over the ending).
Why then would I question his luck? My concern for the golden boy comes less for the actor and more for his characters, who are almost all terribly unlucky. I won't mention them all, but by and large, his roles are that of tortured men who often either die themselves or suffer the death of a loved one (usually a lover). If they survive, it is to a life of hardship and torment. So here's my question to contemplate as you read on: is it the actor who chooses the role or the role that chooses the actor?Let's take a stroll down memory lane of Leo's movie roles, shall we? (oh, but spoiler alert, i do plan to say who dies in each film, all the way through Inception).
I'll start with What's Eating Gilbert Grape, a great performance by our leading man, but clearly a character with lots of problems, from the obvious mental handicap to his disinterested brother to his obese house-bound mother (who dies). 
On to Basketball Diaries. If you've seen this movie, it's pretty self explanatory why it's on my list. A growing drug addiction comes between him and his goal of basketball greatness, leading him to do truly horrible things to sate his appetite for heroin. No, he doesn't die in this one, but his dreams do. 
Oh, Romeo + Juliet, how you shaped my young romantic visions. This is where Leo and I began the love affair we've had in my mind all these years. He was the perfect man to myself and many other young impressionable girls, all of whom felt his angst, which begins as apathy seeking something more, grows to an infatuation with exactly the wrong girl, the forbidden nature of the love adding all the more to its potency, and then the inevitable denouement as first she appears to die, then he dies to be with her, she awakes, finds him dead, and shoots herself beside him. We all know the story, it's an age old tragedy, and his emotive powers brought it home for us.
And then his next tragic love story, Titanic. Sure, plenty of people deride a story that begins with a girl trying to kill herself by jumping off the Titanic pre-iceberg. But I think everyone took a guilty pleasure in Celine Dion after that movie (which I think I showed restraint in only attending in the theater 3 times). Jack, the starving artist who wins tickets onto the largest boat in the world, becomes intrigued by a rich girl with ennui, and has a short lives love affair that ends when they can't both fit on a floating door and his chivalry allows him to freeze to death. Plenty of people got mad at Rose (the adorable Kate Winslet) for allowing him to perish in the frigid North Atlantic, but it's part of his character to save her above himself, and part of why we all loved him so. Alas, once more, he died for love.Now, we didn't see a ton of Leo in the aftermath of Titanic and it's backlash. He did a few strange movies (The Man in the Iron Mask was terrible, The Beach was a strange twisted trip through a mystery island rife with insanity, perhaps a precursor for some of his roles to come later). And I must admit I never saw Gangs of New York. I know, strike against me. But the one that really 
felt like his comeback film was Catch Me If You Can. It was a fun movie, with Tom Hanks chasing him around all over the country and the world as he pretended to be a pilot, a doctor, a lawyer, anything that would help him maintain a lifestyle he never could have afforded legally. But beneath this all is the story of a little boy who watched his parents torn apart by money and just wants a stable life back. He tries to marry a nice girl and be a part of her family, but his lies catch up with him, and she can't take who he really is. But where things really fall apart for him is when he tries to escape (after a stay in Parisian jail) back to his mother, only to find she has made a new family for herself, seemingly forgetting all about him. So our poor downtrodden hero once again is forced to a life of drudgery alone with only Tom Hanks' character by his side.
felt like his comeback film was Catch Me If You Can. It was a fun movie, with Tom Hanks chasing him around all over the country and the world as he pretended to be a pilot, a doctor, a lawyer, anything that would help him maintain a lifestyle he never could have afforded legally. But beneath this all is the story of a little boy who watched his parents torn apart by money and just wants a stable life back. He tries to marry a nice girl and be a part of her family, but his lies catch up with him, and she can't take who he really is. But where things really fall apart for him is when he tries to escape (after a stay in Parisian jail) back to his mother, only to find she has made a new family for herself, seemingly forgetting all about him. So our poor downtrodden hero once again is forced to a life of drudgery alone with only Tom Hanks' character by his side.
And then Aviator. A study in madness via Howard Hughes. I don't think I really need to say much of anything about why this role was profoundly disturbing. Sure, he dated Katharine Hepburn for a while, and was able to fly the Spruce Goose, at least a little ways. But the layers of madness that descend on him thereafter, the lines of jars of urine, the fingernails. Even when he attempts to clean up and pull himself together, the paranoia and compulsions continue to the very end. I think this was the movie that really introduced Leo to us as a serious actor capable of handling complicated and confounding characters.
Thereafter, his movies are all powerful, evocative, and riddled with death and deception. The Departed, a great film, where our hero is bullied into spying on the bad guys from inside, and ultimately killed (though he does get to sleep with the real bad guy (Matt Damon)'s fiancee first). But I believed him as a Bostonian and as a guy coming out of a rough past, trying to make good. However, I think my favorite character in the movie was Mark Walberg's Dignam, I mean what a prick, but eventually, the only one to see through what was really happening and get the last word (or bullet).
In Blood Diamond he's a mercenary (Danny Archer), greedy and looking for his ticket out of Africa and its constant warfare, regardless of who falls by the wayside in his pursuit. It is in this he falls in with Solomon (Djimon Hounsou), a man ripped from his family and desperate to get back to them, as well as Maddy (Jennifer Connelly), a reporter with some useful connections. Together, they fight their way to find a large diamond, Solomon's family, and a way out of Africa. Alas, Archer grows a conscience along the way, and an attachment to his fellow travelers, which leads him to sacrifice himself for their welfare. Once again, our hero dies in this one.
Revolutionary Road (based on a wonderful book by Richard Yates) places Leo once again opposite Titanic costar Kate Winslet in a story of young dreams and ambitions sliding seamlessly into the drudgery of everyday suburban life. The couple who were so hopeful for adventures and opportunities settled for a little cottage in a quiet community, children, and the 50's life of a housewife and bored, unfaithful business man. They decide to make a change, to do something about the monotony of their lives, to move to Paris and just see what happens. Alas, even as they formulate their plans and regain hope, Kate's character becomes pregnant again, and they must face that the financial realities of another baby won't allow them to make this move. The tension of options not legally available in this age flood them until Kate's character finds she must take things into her own hands or drown. Leo is then left to discover his wife bleeding to death, his baby gone, and himself left alone to raise his two remaining children. 
Lest we think this is the worst that could happen to one of his characters, along came Shutter Island. I must admit, once I made my way fully through this movie, I sympathized with old Teddy Daniels (Leo) in wanting to retreat into a world of his own imaginings rather than face reality. Yes, I am giving it all away, I apologize, but I did warn you. Throughout, I enjoyed the great mindfuck of it. By the time he saw rats covering the cliff side, I was starting to wonder just what was up with him (but maybe they had slipped him drugs). Not until he crumbles the plastic gun in his hand after trying to shoot the doctor with it was I convinced. And then the horrible memory returns to him, his insane wife drowning all three of their children, still not seeing that she had done anything wrong, and him finding no choice but to kill her, as much as he loved her. Yes, I think this one takes the cake as his most tortured and destroyed character. And to date, the best mindfuck film he'd done. 
That is, until Inception. I adored this movie. This kind of sci-fi trippy ride is exactly the kind of movie I enjoy. Sliding through other peoples dreams in layer upon layer of non-reality, never quite sure you are really awake, in the real world at all. And we are set up with a man who has been so scarred by previous experiences in the dreamscape of his existence that he can't even trust himself to design the dream worlds anymore. He is haunted, literally, by the memory of his dead wife, who appears to make trouble for him, to punish him for letting her die alone. In the midst of all of this emotional drama, a gang of dream bandits must plant an idea in a man's mind in such a way that it can grow naturally as though spawned in his own mind. This involves three layers deep of dream within a dream, the danger of losing themselves in the limbo of the subconscious mind, and precise timing in order to complete the job before waking. The concept is fabulously intriguing, the actors all contribute (Ellen Page and Joseph Gordon-Levitt notably), and the film is able to leave you not quite sure what's real (to the point of sparking incredible online debate over the ending). I love the movies Leo has been choosing the past few years, and while I hate to see him tortured over and over again, he plays it so well, I can't help enjoying it. I mean, when we are subjected to performances by Nicholas Cage and Keanu Reeves, he's just such a breath of fresh air. So Leo, he's hoping you find more happiness in your real life than on the screen.
