Take Maher for instance, people hate him, and I definitely don't always agree with him, but considering he has been doing political comedy for decades,I respect the shit out of him, and put him in the top tier.

You know... given his longevity and prominence, I have to agree and respect him, even though I find it so damned hard to respect his material.

I know it's the dumbest and most naive reaction to see a superstar and say "anyone could do that", and I try to question the hell out of myself having that reaction to Maher's material on Real Time, and yet I continue to feel that way about the material. It doesn't seem that good. And when he sulks and complains to the audience, "oh, so that offends you", it always seems like an overreaction to the audience not responding to a lame (at best) joke.

To some extent, he MUST be doing right, as you indicate. To some extent, once you have that level of prominence, there's a lot of inertia supporting you--you have people around you to help you maintain your level of material, and the audience has a level of expectation (not to mention the way live studio audiences are directed to laugh hard at everything), where they'll often find your material more funny than it would be from an unknown comic.

Having said all that, I still find Maher's Real Time material sorely lacking--and I realize some of this has to be my own short-sightedness in not appreciating what he's doing--and I'm painfully aware that some of his position is due to the connections and status he can use to get guests, and that a moderate ability to interact with their own material and energy can alchemize into a better product than what Maher himself is contributing. (Let alone the contribution of any professional writers on his staff.)