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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.

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.