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A Jerkass is a character who is so completely obnoxious that it is unbelievable anyone would willingly interact with him; let's face it, this character is schadenfreude incarnate.
There can be numerous types of Jerkasses - some are polite, intelligent, charming, handsome and/or brave, but still give off a basic air of arrogant, snobby, sneering, leering prickery that makes them such a nasty little punk that you wonder why nobody's shanked them or busted a cap in their skull yet. Others are more obvious assholes who may be racist, stupid, or just basically unpleasant. Either way, it's usually their status on the team of "good guy" that results in them never being called out on it. After all, if they were an asshole on team "bad guy", they'd just be a villain.
What makes him or her entertaining is the fact that you don't have to deal with them yourself in real life. Usually, the Rule of Funny enables the people around the person to be able to live under the same roof as them without, y'know, blowing their brains out. Sometimes, the Jerkass is the Plucky Comic Relief who's stepped off the beam and become The Scrappy, in which case the Rule of Funny fades away; they may be okay in the other characters' eyes, but the audience would still love to punch them in the face. Because of this, it's hard to feel sorry for them when something bad does happen to them, and it is often seen as comeuppance.
This is especially disconcerting in any series following a team that needs to be coordinated and would realistically not put up with this kind of behavior. This can also happen with a hardass or grouchy character who becomes an obstacle to others rather than providing pragmatic, but perhaps unpopular, advice. In films, they often get their comeuppance in the end, which will be applauded by the audience.
The single factor that pushes a merely annoying character over the line into full-time Jerkass status is their absolute obliviousness to other people's perceptions of them. Nothing they do ever strikes them as out of proportion; they never realize that anything they are doing might ever be considered inappropriate, excessive, or cruel; in fact, they believe they are actually right and everyone around them is in the wrong. If anyone ever does call them out on their Jerkassery, expect them to just rationalize it or shrug the accusation off. If the writers don't put it in check and just keep trying to one-up the character's assholishness, it can deterioate into The Sociopath.
The Neidermeyer is a military-specific version of this character type. Similarly, the Unsatisfiable Customer is frequently this in a restaurant or retail scenario. Internet trolls can be a Real Life example, and rely on GIFT anonymity to get away with what they do.
The Jerk with a Heart of Gold talks the talk but doesn't walk the walk, being a basically nice person underneath despite a rough outside. When a character is intentionally pretending to be a Jerkass in order to keep people from getting close to him for whatever reason, he's putting up a Jerkass Facade. Keep in mind that pretty much everybody on a show acts like a jerk at some point, such as when the Butt Monkey gets pushed too far, but this does not make them a Jerkass.
Self-serving Jerkass who measures out "justified retribution" against their victim of the day for a perceived slight? They're either Karmic Tricksters or Chaotic Neutral and therefore made of at least 65% grade A Jerkass. The remainder are the good things which keep them from falling into Chaotic Evil territory though not by much given the rarity of their presence.
If you still root for them in spite of their apparent lack of redeeming qualities, it's Draco in Leather Pants. If it's clear they really are a jerk but nonetheless have redeeming qualities and a Dark and Troubled Past, you've got a Jerkass Woobie.
There is a certain level of subjectivity in this trope. One troper may find character X to be a total Jerkass wheras another troper may find character X to be the Only Sane Man in a Crapsack World using snarky complaining to keep his sanity. This can be boiled down to members of the audience having different values and thus judging the same character traits differently. As such, with all examples listed below, Your Mileage May Vary.
See also The Jerk Index.
No Real Life Examples, Please. We do not wish to have any Flame Wars erupting here about the matter and many Jerkass attitudes in Real Life tend to be rather subjective. Not to mention that some people that call out someone as a Jerkass tend to do it in a Jerkass-like attitude themselves, and that just makes our heads spin.
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