That Obama joke fell flat because it was stupid. Rickles acts like Obama was a former NBA player or something. Obama was a mere bench player (a 3-point specialist, apparently) for the Punahou High School basketball team. He did not even play basketball on any official team at Occidental College or Columbia University— just pickup games and intramural squads. His set up wasn’t bad— some WH crisis and how Obama would react— but the punchline was garbage.
Still, it is amazing that he looks as healthy as he does at 82.
You forgot to mention Zero’s career selling crack to his teammates. I’m so glad that we have been able as a nation to move beyond the fact that george Bush had a few beers in his youth to the relatively insignificant fact that Obamanation, whose picture will stand along side george Washington’s, was a crack head, a crack addict and sold crack to other kids to feed his habit. Gee, what an intelligent electorate we have.
Rickles mocks and defuses "stupid" ethnic stereotypes. In this case it is the old stereotype, "black guy = basketball player". When Rickles gets going in his act, people laugh at that kind of humor.
If Obama was a former NBA player then the joke would not have been a Rickles-type joke.
Laugh at it or not, call it a stupid joke or not, with your above long explanation of how the joke would have been funny, you miss the Rickles formula.