Why? Because to me they more closely resemble real life.
Sure, there are times when I succeed in my goals and feel really great about it. Likewise, there are moments when I fail in my efforts and feel really miserable about it (unfortunately more the latter, than the former). But rarely does life ever work out this nicely. More frequently, I find that I achieve my goals at the expense of my own personal life or I find that failing miserably turned out to be the best thing for me. Either way, it seems these outcomes happen more often than all-out triumphs or tragedies.
The only drawback with identifying these kinds of stories is that there isn't a great one-word term to explain them like there is with triumphs or tragedies. In a general sense they can be called "bittersweet," but even this isn't as accurate as it should be. Which is more prevalent, the bitter or the sweet? And to what part of the story does it apply? Bittersweet accurately describes the general feeling these kinds of stories have, but it's not too helpful in the actual creation of a story.
Because the Main Character is such an integral part of a story's meaning it can sometimes be helpful to use their emotional state as a kind of benchmark by which to evaluate the ending of a story. With this in mind, the "Bittersweet" ending can be divided into two categories: the Personal Triumph story and the Personal Tragedy story. The second (my ultimate favorite) will be looked at in greater depth in the following article, but for now, I'd like to focus on the sweeter part of bittersweet.
The Personal Triumph
These are the stories where the good guys lose, yet the Main Character goes home happy. As always, I've tried to put together a collection of clips illustrating this concept.
The first clip comes from the popular film, The Devil Wears Prada. In this story, Andy Sachs (Anne Hathaway) is the "good guy" trying to succeed in her attempts to be the assistant to Miranda Priestley (Meryl Streep). As the clip above shows though, things don't quite work out the way Andy thought they would.
Having grown to a point where she can confidently make the decision her heart wants her to, Andy turns away and chooses a life of tweed over one of Prada. However, even though she blew it, she still ends up gaining Miranda's approval. The good guy (or in this case gal) loses, yet goes home happy -- a perfect example of a Personal Triumph story.
In Donnie Darko, the same kind of ending exists. If you haven't yet seen this film, you should probably skip the next couple of paragraphs -- it won't make any sense at all (it might not make sense even if you have seen it!)
Just moments before he is crushed by the jet engine, Donnie starts laughing hysterically. Why? Because he is no longer worried about dying alone. Although we don't see the actual act, it's safe to assume that his relationship with Gretchen has grown to a point where he doesn't feel like he's alone in the world anymore (i.e, they slept together). Donnie has love. The Main Character, who started out in a catatonic state, ends up going home happy.
But where does this leave the rest of the world?
Unfortunately, Donnie's acceptance of his own death reverts the Primary Universe back to its miserable state. The alienation and the fixed conservative attitudes, which are the real source of the problems in the story, continue on.
Gretchen asks Donnie, "Wouldn't it be great if we could go back in time and erase all that pain and suffering?" But even a time-traveling superhero like Donnie can't outrun the past. Whatever happened, will always be. Dukakis will lose, Jim Cunningham (Patrick Swayze) will continue to abuse children and Cherita will still be ridiculed by the other kids in her class.
Donnie could have let this world end by refusing to go back in time. In doing so, he would have brought an end to all of the painful and incompatible attitudes and the good guys would have won. But he didn't. He found a connection that he never thought he would and felt that that was enough of a life.
The Main Character goes home happy, yet the world as a whole, the "good guys" that we are rooting for, end up losing.
Last up is the Academy Award-winning Rain Man. In case it's been awhile since you've seen the film, Charlie Babbitt (Tom Cruise) abducts his brother Raymond (Dustin Hoffman) in hopes that he can ransom him for an inheritance. Along the way Charlie grows to love his brother and ultimately, decides to give up the inheritance. His brother means more to him now than any amount of money ever could. The "good guy" loses, yet goes home happy.
Much simpler to explain than Donnie Darko, but no less meaningful.
Feeling Good About Losing Out
In short, that's what these stories mean and why they feel the way they do. The audiences feels good about losing. Three completely different genres: a popular chick lit flick, an indie fan-favorite and an Academy Award winner -- all with the same kind of ending. In giving audiences something closer resembling real life, these films become cherished experiences that outlast the usual mindless drivel found in most theaters.