I don't think that they are difficult to understand. i suppose every language has its own peculiarities. I know for sure that some jokes in Russian can't be translated because of the "the play of words" we call it this way.
To my mind your understanding of a joke depends on the kind of humor that you prefer. A person who adores the primitive physical jokes will never understand O'Henry. it is obvious, i suppose.
By the way, i remember the so-called joke that made me think of it more than twenty minutes before I understood the humor.
Two men met each other and chattered about their latest news. One said: My wife decided to have a holiday on an island. Another man reacted: Jamaica? and the first answered: no, she decided on her own.
later i knew that the joke was a very famous one and everyone knew it. but personally I was astonished with the jibe.