I recognize that this is more of an issue in tv shows, movies, and games than it is in written stories, but I feel like the points that I make will still stand. There's nothing wrong with wanting to write a cool character. If you want to write a character that is the epitome of cool, that makes your reader go, "Wow, I wish I were that cool," when they read them, that's fine. That is totally your prerogative. However, as with many things, you have to have some sort of balance in that badassery, or else it just goes over the top and stops being cool and just becomes silly.
Unfortunately, this is totally a subjective thing. What I think is the coolest thing in the world, someone else might find to be incredibly lame and try-hard, or vice versa. And even more unfortunate, one of us may be in the majority opinion, and the other in the vast minority. And in my case, very frequently I am in the vast minority when it comes to opinions on what is cool.
I can try and write my own versions of cool, and I might think they're cool characters, and you might think they're cool, but lots of others might not. And further still, what is cool is not necessarily a consistent thing. Many ideas of what is cool is based on current culture, which may change at any moment, and there's no way to predict what will last and what won't. This is easily seen looking back. There are thousands of things that we can look back on, and think, "Why did we ever think that was cool?"
But when you're trying to write a cool character, those are the factors that we have to draw on. The very act of trying to make something cool is effectively putting a date on it, showing when it was made and when it was actually considered cool. And with the long amounts of time that it takes to produce a story, by the time you're finished, the things that made your characters cool may not even be cool anymore. That means rewriting them. But that takes time. And by the time you're finished...
You get the point.
Many of our opinions of cool are based on what used to be cool, as well. By trying to pull on these things, we are alienating people who never experienced those things as being cool. But we probably don't even realize that we're doing that, because to us they never stopped being cool.
It boils down to a simple fact: a character can be cool, but chances are that coolness won't last. Which may not be a bad thing. We can leave a mark in our writings to say what things used to be, and that's perfectly alright. We may even choose to write intentionally in ways that used to be cool but are no longer, in order to date the characters themselves and set them on a page in history. Perhaps this can be used to hold them back in the story, or give them something to work towards in the future.
Personally, I wouldn't want a character of mine to be defined as being cool. But I suppose, in a way, I'm not the person who gets to decide that anyway.
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