I think1 what you're looking for here is that, in Gricean terms, Chris is flouting the maxim of relation, which here means that you don't make an analogy unless that analogy is relevant to the conversation.
The surface context is an implicit assumption that Martin wouldn't normally hire someone with no shirt. Chris is certainly accepting that much—his reply makes no sense otherwise, but it makes perfect sense given that assumption: If Martin wouldn't normally hire someone with no shirt, but he hired a guy with no shirt, there must be some compensating factor—maybe the guy had really nice pants.
But there's more going on: Martin is offering the story of the guy with no shirt for a reason, as an analogy to something about Chris's condition. And, given the maxim of relation, that analogy must be relevant to the situation. So, Chris should interpret it as an explanation for why Martin isn't going to hire him.
Chris presumably understands that, and facetiously appears to ignore it. Facetious replies often involve flouting a maxim like this.
But this isn't just a joke. At the same time he's flouting the maxim of relation, he's relying on the same maxim to make a point. His extended version of the analogy is meant to be relevant to the situation. So he's implying that he's not like a guy with no shirt who Martin would never hire, he's like a guy with no shirt who Martin did hire, because he had really nice pants. Therefore, Martin should hire him, because he has… well, he hasn't implied what he has, only that it's something that compensates for the surface reason to reject him.2
1. I don't know this movie, and I don't know the context—but I think it's a Will Smith movie, and I know how Will Smith characters usually talk, so I can take a solid guess…
2. If this is a sales job, that something could even be his facility for turning things around this way. The way Will Smith characters tend to converse is a lot like the way successful salesmen convince people to buy things.