A job is more than just money for services rendered (Which he desperately needs right now), it will solve a lot of issues for him:
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Self-Esteem: Yes, despite his ginormous ego, he has clear self-esteem issues from seeing all of his past classmates go on to bigger & better things, while he is still essentially living the same life. This is an
old video, but you can clearly see his freudian slip there. He knows his life is out of whack, and with the free time he has, he clearly ruminates on it. This is partly why he would come up unprompted with stuff like 'I learned my lessons..etc", because he NEEDS his past 8-9 years or so to count for something other than him being publicly humiliated on the internet. A job will at least give him a sense of purpose he hugely lacks and something to wake up for. Even if it is stacking shelves at a Wal-Mart or something.
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Building Common Sense: This will likely be our biggest point of agreement, Chris is the opposite of common sense, this is because he doesn't interact with people past arms-length transactions like buying fast food or toys. If he gets a job, he will have to deal with customers, coworkers, managers. He will be able to get good advice on things like relationships, good uses of money etc.
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Making Friends: Chris is incredibly lonely, he may have friends that are willing to tolerate him for the length of a movie or something or are willing to be with him @ Pokemon club, but he has no real friends, the kind that check on you when you've been gone too long, the kind you can call for a cup of coffee at a moments' notice. This is why you see him trying to make friends with celebs, he is not creeping on them, he is merely trying to make friends like a dog is chasing random cars. Of course being Chris, he set the standard of potential friend way too high, as he did with other things during his life.
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Hygiene: Any company that will let him join them will certainly insist on him being clean and not looking/smelling like a hobo. Of course I realize that's half the reason he won't try for a job in the 1st place..
I realize this doesn't entirely solve his incredible array of issues, but it should enable him to be functional at least while working on the rest.