There's an honesty and realness about him and his humor. It's doesn't come off as trying to be clever, but at the same time, it's some of the most clever stuff out there. It's blunt and subtle at the same time. You're right, it's hard to explain. Most comedians, when they're "on" and being funny, are obviously trying to be funny. Which isn't a BAD thing. I mean, of course they're trying to be funny, it's what they do. But Norm has this ability to be incredibly hilarious and say the funniest shit, but at the same time seem completely chill about it, like he wasn't even trying, and, I think most importantly, like he doesn't even care if other people find it funny. I think that's the key, now that I mention it. He's said in interviews that he actually enjoys bombing, because the situation of a comedian bombing is hilarious to him. This kind of outlook comes through in his comedy.

Generally, I think Norm's brand of comedy is sort of an exact flip flop of most mainstream comedy; most comics address issues that seem subversive, but do it in what is actually a very broad way. They discuss "topical" subjects in a manor that gives off this facade of being insightful. They're outwardly subversive but actually somewhat safe or "normal". They have to be. People only think it's funny when they already agree with the message. Norm, on the other hand, is the opposite. Humor that is outwardly very broad and base and silly, but in an actually subversive way. You often get that, and I'm not sure how else to put this, that the joke itself is the joke. Most comedians tell shallow jokes about deep subjects. Norm tells deep jokes about shallow subjects, and is more subversive and generally funnier for it. Of course, attitude only goes so far. On top of his unorthodox approach, he is also incredibly witty, and much more intelligent than people probably give him credit for.

Let's look at one of his jokes for analysis: "Opinion's are like assholes, Neil Patrick Harris likes to sick his cock in them. Oh wait, that's just assholes." It's hard to explain what's so funny about this. On the surface, it's a gay slash cock joke. But it's funnier than that. Everyone's heard some self-righteous person give the whole "opinions are like assholes" or "opinions are like penis" spiel, as if they were some kind of prophet floating above all the petty conflicts of the day. Often, nowadays, this will be in reference to someone's overt homophobia, which is, I feel, a crucial part of the underlying comedy. Norm takes this phrase and perfectly subverts it by turning it into, what else, a gay joke. It also subverts the cause. Once again, the phrase being subverted here is often used to speak out against homophobic opinions, essentially defending gay rights by likening opposing opinions to something as ugly as an asshole. Norm is not anti-gay by any means; however, I think he recognizes the inherent silliness of getting all high and mighty about what boils down to a bunch of guys who fucking each other in the ass. This joke isn't anti-gay, but it is subversive in that way it tries to bring the self-righteous people who would use the actual phrase back down to earth. He keeps it real.