Eggman and the Gheez go way back, I think quiplash might have been their first segment together on the NLSS, but Cerso's duel against Thornforg in Andor Landor marked the vanquishing of their rivalry.
I don't really get the NL dan dynamics now. Ryan just seems to comment on his play as if Dan is doing bad at the game, when in fact Dan is pretty good at Isaac compared to average. Meanwhile Dan is pumping the energy with great ease!
You gotta remember isaac is NL's domain. There is precisely one video game where NL feels confident saying he is just genuinely good, and that is Isaac. Whilst he (and us) loves Dan, he still finds it funny watching him play. Def check out their co-op series if you haven't already, it's this dynamic writ large
I think the dynamic is that they're close enough friends that NL can dunk on him and it makes sense in the context of the friendship. Dan has a good head on his shoulders for it too.