@izzythepush,
Almost anything can be funny if context is carefully worked out. I think Carlins examples of Elmer Fudd and Porky Pig are funny because he goes and creates n insane context.
Dales lines were just basically unfunny because his use of "Rapist" had little context,(so then it just sounds insensitive) .However, prhaps if he would include it as being a component of education, he should have considered trying to focus on Catholic Parochial schools and the sex deviant priests. That'd be funny.
"I work in a school, Im a Randy Priest"
Comedy's tough
Self deprecation is safe because I can joke about almost anything if I am the subject. Substitution of insane characters or cartoon characters can become (sorta) self-deprecation (especially if the comedian tries to "seriously"explain the characters motives in doing whatever hes doing)
Carlin was trying to xplain that Elmer Fudd had this hard-on and needed to seek som relief. I find that funny, after having introduced "Porky" Pig based on what his name means in the urban dictionary.
Political edgy-ness requires great care. Louis CK makes it sound more artificially presented than George Carlin ever did.