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These kinds of remarks get chuckles for the basic reason that we like to pat ourselves on the back for recognizing a pattern and having the thing we watch acknowledge it as such. Considering the sheer degree of prevalence the isekai genre has enjoyed ever since the early 2010s, no doubt because it provides publishers like Kadokawa a lot of money, it makes sense that isekai too would become susceptible to these kinds of remarks from its own works.
But *The Eminence in Shadow* makes the mistake of assuming that being meta is the same as being funny or a worthwhile piece of entertainment. Glimpsing the greater picture, or making casual reference to things that viewers would recognize, is perhaps a short-term solution. But that does not guarantee that the inner substance of the story will be able to stand on its own two feet, either. Within its audience-conscious asides, it attempts to fashion a fantastical story of Cid Kagenou, a fashions-himself-as-the-ultimate-warrior man who attempts to make the best of both worlds, so to speak. Treating his reincarnated situation as the chance to live out his ultimate fantasy, he adopts the moniker of the background everyman archetype on one hand and the “Eminence in Shadow” in the other. Getting involved, investigating, and dispensing his own form of justice when he sees fit, he treats his new environment as a playground rather than being full of actual people with consequences.
Therein lies its initial draw, and its first real gag; take the common thought that many isekai protagonists have (that they’re either dreaming / don’t take their new situation seriously enough), and have it last for the entire show. This gag quickly devolves into overreliance; *The Eminence in Shadow* spends so much of its time with Cid making jokes about the isekai world, drawing upon his knowledge of its conventions and general structure. But the show is confusing its meta remarks for comedic cleverness.