The characters you like should suffer
Protagonists without challenges are boring. James Bond is superhuman in every sense of the word, but he makes a good protagonist because he's pitched into impossible scenarios where even his natural gifts don't let him succeed effortlessly. He suffers, he struggles, and at the end he beats up the bad guys and flies home with a grin on his face. Absurd, yes, but it speaks to a fundamental issue about characters in that we root for the people who suffer.
That extends to roleplaying as well, which means that the characters you like the most are often in the worst positions. Your heroes are the ones who lose everything, fall in love with the wrong people, and get beaten at the worst possible time. How badly you treat a character is an indicator of how much you genuinely like that character. The ones who live a blessed life are the antagonists.
Other players can see the same thing. If your character succeeds at everything by virtue of being there, there's no real cause to root for him. We're intensely suspicious of anyone who gets rewarded for no real effort. And the odd thing is that it never stops -- no matter how high your character goes from sheer pluck and determination, he needs to still be struggling and just one step away from failure. He needs to have significant obstacles, preferrably those he places in his own way.
Happiness is fleeting for the characters you like, but it's more intense. It gives the sense of a major accomplishment, that however bad everything else might still be you managed to do something just right. And it keeps you moving forward.
The characters you don't like are there for drama
When I'm playing a character I like, I really don't have to be consciously roleplaying at any given moment. I slip into the character's mindset, but I can do that without interacting constantly with others. When visitors come calling, I'm ready, but it's not necessary.
Not so with characters I don't like. If I'm playing someone I know is awful in every way, shape, and form, I want him to be out there in the mud at every opportunity. If there's nothing else going on, I'd just as soon leave him on the shelf for a while.
Why? Because characters you already know to be awful are also characters you don't particularly like to be for an extended period of time. I'm perfectly happy to play characters who are maliciously dismissive of others and manipulate the world around them into a convenient shape, but I don't actually want to think like them for long stretches of the day. It's uncomfortable, like putting on filthy clothes and walking around for a day. You feel dirty on a tangible level.
That's not to say I won't play these characters, just that I won't play them for the sheer joy of stepping into someone else's shoes. These shoes are not pleasant. That's kind of the point.
The characters you like are more unexpected
Considering the dramatic need for things like villains, there are always going to be some characters I make with the full knowledge that I won't like them very much. One of my recurring characters is a particularly vile man, and I know every time I create him in a new game that he's not going to be a comfortable character to play. He's going to do awful things, he's going to deserve awful consequences, and eventually he'll get them.
But most of the characters who are comfortable to play turn out to be surprises. Characters I created just to see where they'd go and how they'd do in a given environment. And the usual answer involves unexpected directions that create a certain amount of warmth.
There have been distinct moments when I knew that some of my characters were winners. Others have just slowly become more and more familiar over time, characters who always are fun to join in an adventure no matter how low-key it might seem. Sometimes I'll recreate them and find that they don't lend themselves to a given setting, but when one of them comes into his or her own again, it's like finding a new take on an old favorite.
I don't think there's any coherent way to really cap off this discussion, so I'm not going to shoehorn a neat little conclusion in. Feel free to share your own observations on characters you like or dislike and what impact that has via mail to email@example.com or down in the comments below. Next week I'm going to chat about music, and the week after that will be a look toward another profession that wants to end up with all the toys.
Every Friday, Eliot Lefebvre fills a column up with excellent advice on investing money, writing award-winning novels, and being elected to public office. Then he removes all of that, and you're left with Storyboard, which focuses on roleplaying in MMOs. It won't help you get elected, but it will help you pretend you did.