I have to admit that I don’t remember this dude, but after a quick glance at memory alpha, he definitely looks the part! Just get him some sunglasses, a hat, and some pocket sand.
Comedy can be a minefield for this type of stuff. I’m a big fan of the comedians that can dance around the edge, or seem to cross it and then bring the audience back, eg: Mark Normand, Bill Burr, Jimmy Carr, a lot of the old Norm MacDonald stuff, etc.
But I’ll see some fan compilations with titles or comments that make it clear that they don’t get the style of humor… Like “[comedian] DESTROYS feminists!!1!”
When, to anyone with a reasonable level of social intelligence, it’s abundantly clear that that’s not what’s happening.