* CrossesTheLineTwice: A master of this practice. It was his personal philosophy that it was the duty of the comedian to find out where the line was drawn and cross it deliberately, then bring the audience along and make them happy that he did.[[note]]That last part is often lost on modern users of this trope.[[/note]]
** His bit about BlackComedyRape starts off like this and gleefully plays double-dutch at every preceding opportunity.
--->'''George Carlin:''' Want to piss off a feminist? Call her a cum-catcher, that'll get her attention!
--->''(Audience groans)''
--->'''George Carlin:''' Oh, don't act disgusted! Don't act disgusted! Half of you are gonna go home and go down on each other tonight, remember? If you're willing to swallow cum, let's not make believe that something I said was disgusting!
** During his "Capital Punishment" routine:
--->Instead of an axe, you do the beheadings with a ''handsaw''! ''(Audience groans)'' Hey, don't bail out on me now, goddammit! The blood is already on our hands; all we're talking about is a matter of degree!
* FunnyAneurysmMoment: ''It's Bad For Ya'', his posthumous final performance, features a lot of routines about death, a fact which was not lost on his surviving family. His daughter Brenda made several allusions to his "Things We Say When People Die" bit at his funeral, knowing George would have wanted them to laugh. [[SugarWiki/HeartwarmingMoments Which they did]].
* HarsherInHindsight:
** His rant on 1999's ''You Are All Diseased'' about how pointless airport security was and how he didn't believe terrorists were out to hijack planes quickly became this only 2 years later when, in fact, terrorists DID hijack planes.
** His ''Fuck Lance Armstrong'' became this, or HilariousInHindsight when he was revealed to dabble with steroids. He also dismissed Tiger Woods harshly, and this was before Woods' infidelity and career crashed.