I'm catching up on the stream and although it would be nice, in a perfect little world, if Cobra could get under Keem's umbrella because he would try to do good things for him. Keem likes looking like the good guy and he made sure to bring up Josh's teeth and I know getting them replaced with a set of Boogie Biters is what's going through his head right now. He'll want to send a fat retard or two to film it and probably make up for the costs with donos.
I think
@Irregardless is right though, getting Josh to do anything is next to impossible. Keem would have to suck up to him and be as nice as possible all the time. Josh would just have to be the punishment guru or something but if he has to come up with anything creative he'll shut down. Maybe he could get kid behind the camera to wrangle him because Josh liked angry grandpa so much but even that might be a bridge too far. Keem is also going to have to eventually deal with the fact that Cobra is a severe alcoholic, people will start shitting on him for enabling or whatever and Keem want to make it a thing. Say goodbye to Josh the second it's hinted that he stops drinking.
That being said, I'd be curious to see the attempt, if only to see how Cobes would destroy it and it's not like he does all that much anyway.