Not the hero we need but the jerk we deserve
Let's start with the most basic trick to get your character into the group even though he's a jerk: He provides a service that everyone else needs. If the only way to get to Alderaan is to deal with an obvious lying swindler, then you're going to have to deal with that lying swindler, and when it turns out you've pulled him into a bigger mess, you're going to keep moving along with him out of momentum. Part of what makes Star Wars work is that Han Solo is a jerk right up front, but he keeps getting pulled into the plot or pulled along by it, and the other characters need his help for various reasons. (The other part is one I'll get to in a minute.)
Obviously, this is something you have to work out with other players beforehand, but it works well enough for the basic function of keeping a guy around even when people might not like him. He provides one function or another that no one else can replicate. Maybe he's a pilot, maybe he's an exceptional accountant, maybe he's just the one armorsmith who will actually work with someone else. Remember that poverty and geography can play a role as well -- your guild might not like this guy, but he's the only lawyer you can hire after an earlier mess.
Bear in mind, however, that this works only to get your foot in the door. Eventually someone else is going to come along, someone who provides the skill with none of the accompanying background noise, or at least enough of the skill to work with. Similarly, being an amazing warrior is not reason enough to keep a jerk around. Most games are filled to the brim with those sorts of characters. You can get a master swordsman anywhere; most of them aren't misogynistic, autocratic tools.
In the event that your character has no useful skills -- or no useful relevant skills -- you can always fall back on the time-honored defense of not being an enormous jerk for the five minutes it takes to make a positive first impression.
I'm not a jerk, but I play one almost all of the time
Most people are not just plain nasty. They act that way for a reason. Usually, someone who keeps everyone else at arm's length is trying to specifically avoid any close personal connections for one reason or another. So it speaks for a lot when your jerk actually goes out of his way to help someone else. (Yes, the original Star Wars films get credit for this again. I told you I'd get to it in a minute.)
I'm not talking about doing so as a byproduct or an accidental result of something else (though you can certainly claim it after the fact). I'm talking about going out of your way to do something for another person or persons that looks like a gesture of magnanimity for pretty much any definition you care to use. Oh, sure, you claim it was because you just wanted to shut someone up or you didn't need the money or whatever, but that's an obvious excuse made after the fact.
When you have trouble playing jerks with hidden depths, the trouble often comes down to those hidden depths never surfacing. Bring them to the surface, even if it's just briefly, from an early point. Rielene, who got highlighted in earlier columns, was kind of a jerk, but it was because she was desperately afraid of getting close to someone else again. She also went to bat for the people she claimed not to care about on more than one occasion because she did care. Her real problem was caring too much rather than not enough.
That doesn't mean you should be afraid to play your jerk as a jerk. Just don't be afraid to break through the nasty facade on occasion so that people see that there are depths there, even if they aren't always readily accessible.
A steady hand on the jerk
The greatest danger with any jerk character is that you start acting like a jerk to players on the basis of this being how your character should act. Sorry that my character chopped off your arm and then burned your house down, Phil, but you know, he's a jerk! Always being a jerk to others; can't control that adorable little scamp.
But you can. And so it is more than worth considering the biggest collection of jerks ever assembled for television: Seinfeld.
For those of you who have never seen Seinfeld, you are too young to be using a computer. Go get your parents to put you back in the crib. But if you can still see the computer from the crib, it was the origin of several comedy tropes that have since been adopted in pretty much every sitcom ever. It was also populated exclusively by selfish, short-sighted, amoral jerks. (I'm told It's Always Sunny in Philadelphia occupies a similar niche.) These were awful people who would stab one another in the back with only the slightest hesitation.
In theory, anyway. In practice, they all got along for the most part because it would kind of kill the entire premise of the show if they openly tried to murder one another. So while tempers flared, everything was kept under control by the writers, who were in complete control of what the characters did.
The same is true for you. Yes, I'm the first person to advocate letting your character speak and being true to the essence of the concept, but there's also a time to remember that you are playing a game and do not want to completely ruin everyone's experience. Your character gets a voice, but you as the player get veto power, and it's important to exercise that power on occasion. Otherwise I'm not going to think the problem is the character's impulse control.
As always, feedback is welcome through mail to email@example.com or in the comment section. Next week, I want to talk about hinting at hidden traits without being too obvious or too obtuse.
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.