Speaking from a purely visual standpoint, Chris only needs a trip to the barber and a set of decent clothes to be passable.
He only needs a shower to not turn others away with his BO.
You're talking about getting a job, not actually keeping one. A set of decent clothes and not being smelly for one day isn't going to cut it.
For one, even for getting a job, it won't get past a job history that literally doesn't exist. "I've never had a job in my freaking life" isn't a resume. They're going to ask why. And he has no good explanation.
Then, getting past getting a job, which isn't itself impossible, but would be difficult even for a normal person with his job history, he has to keep it.
One shower isn't going to do that. He'd need to revolutionize his personal habits to make even basic hygiene a part of them. He'd have to get a habit of actually going to the barber, and actually wearing many sets of decent clothes, washing them, and so on. He'd also have to manage not to sperg out in socially unacceptable ways, not just as long as a job interview, but every single day he goes to work, for at least 40 hours a week.
If he even managed it temporarily, it would lose him his guaranteed tugboat income and have to reapply when he inevitably lost his job, something he wouldn't be capable of navigating easily or without legal assistance, potentially waiting for years to re-qualify.
So it would be a really insanely dumb gamble, even by Chris standards, to throw away a sure thing to make a majorly dicey attempt to get a job and keep one for the rest of his life. If I were advising Chris, I'd say stick with the tugboat.