It’s really hard to explain, because really, he’s not that funny, but I find that hilarious!

Like the moth story, or Uncle Frank in 'Nam, he just creates this awkward tension where you know your listening to a joke, but this guy is saying just such depressing or horrific shit while keeping a slightly goofy tone. You expect a punchline around every corner, but he just keeps dragging you in, and you’re wondering how this terrible story is going to be funny, and he hits you with a mediocre punchline that any third grader could have seen coming a mile away, but he’s built so much tension and sucked you into this story and you couldn’t see what was right in front of you the whole time.

He’s not telling a joke, he’s playing a joke on YOU. That could be part of why people either love him or hate him. As long as there’s no harm, I’ll be the first to laugh at a joke played on me, but I know there are others that don’t appreciate that at all.