So the question is whether the title implies you can make a living by being a jerk, or merely while at the same time being a jerk. It’s an important distinction. Donald Trump has certainly made a living while being a jerk. But does he make a living by being a jerk? Does his income derive, at least partly, from his jerkiness? Charlie Sheen was fired from his day job for being a jerk, but has managed to use his jerkitude to launch a new career. Mel Gibson, by contrast, managed to integrate his jerkosity into his film career.
This goes right to the question of what celebrity is, because a celebrity is someone who is the product. They get paid just to be themselves in various contexts … talk shows, public appearances, etc. All they’ve got to do is show up. (Of course, many also try to do something self-aggrandizing at each event to maintain their celebrity status.)
Donald Trump originally made a living by investing in real estate. Now all he has to do is be himself and money rolls in. Charlie Sheen only had to be born to be a celebrity, but now he clearly supplements his income and reputation by being a jerk. And Mel Gibson? Well, he's just a very successful jerk.
So what does this mean for the rest of us? Can we all enjoy the wealth and fame of celebrity jerks? It’s tempting to think so, but remember that for every one of these jerk superstars, there are millions of jerks who still have to go out and work for a living.