I am no expert on comedy and I’m certainly not a historian of comedy. My experience with Don Rickles is that he made me laugh when I was less than ten years old by telling off-color jokes about people’s race and ethnicity. And then he mostly disappeared, except maybe he would turn up to do a cameo on Newhart or something. Every once in a while, I’d see him doing a roast where he was still making racist and ethnic jokes that I no longer found remotely amusing. Whenever I devoted a moment’s time to thinking about him, it was always to ponder briefly why he insisted on not changing with the times. The one thing no one should be surprised about is that Rickles would tell a joke about the president coming over to mop his house. That’s his level of humor. What he seems to miss is that you can make a funny joke by mildly playing on racial or ethnic stereotypes if those stereotypes are kind of accurate. The reason polack jokes aren’t very funny is that, in most people’s experience, Poles aren’t especially stupid. The reason that a joke about the president mopping floors isn’t funny is because the president is an extremely smart and talented man. Rickles was warmer a few years ago when he attempted to make people laugh by making a joke about the president playing basketball during a national security emergency. It might have worked if the president wasn’t also an avid golfer.
Obviously, racial and ethnic jokes are best-told by members of the group that is being spoofed. But that’s not mandatory. What matters is that your joke strike people as both essentially true and not meant in any kind of mean-spirited way. Rickles, is seems to me, totally forgets the first part of this formula and goes out of his way to violate the second part. He relies on his jovial personality and a few comedy techniques to try to take the sting out of his meanness. But it rarely works.
One thing I think Poppy Bush shares with Barack Obama is that he was hard to ridicule. Dana Carvey had some success mocking Poppy’s syntax, but he was basically alone in making any headway. Poppy’s sins were too serious and his personal traits too muted to make him easy to parody. The president is so even-keeled and competent that almost all jokes about him just fall flat. Basically, you’ve got those ears and not much else.