My thoughts on him after watching quite a lot for several years... He calls himself a "Traditionalist," and really, that's the most accurate description I can come up with for him. He reminds me of a slightly less intense version of Dana Carvey's "Grumpy Old Man"...
"In my day, we didn't have safety standards for toys. We got rusty nails and big bags of broken glass! That's the way it was, and we liked it! We loved it!"
"In my day we didn't have hair dryers, if you wanted to blow-dry your hair, you had to step outside in the middle of a hurricane! You would get your hair dried but you would also get a sharp piece of wood driven clean through your skull--'Look, I'm a human head kebab!'--that's the way it was and we liked it, we loved it!
I think it's hilarious when he says to his guest, "I'll give you the last word." And then, in absolutely EVERY instance, he follows up or contradicts whatever they say. He does this with an absolutely straight face. Does he really not see the humor here? Does he not realize what it means to give someone "the last word?"
That said, I'll also defend him from people who would compare him to, for instance, Sean Hannity. To me, while I frequently agree with Mr. Hannity, it is clear that he is a Republican "talking points" parrot. Is he pretty good at it? Sure. Do I have the sense that he is genuinely trying to be fair in his presentation? Not whatsoever.
On the other hand, I truly believe Bill O'Reilly thinks he is "looking out for the folks." He tries to be fair, and if you want to be fair, you will notice that he is every bit as ready to condemn the typical Republican than he is the typical Democrat. It's true: he wants things to be the way they used to be--and this reminds us of, and often places him in the corner with, conservatives. But he's as angrily vocal as any commentator you will ever find on the subject of those "greedy" corporations who reward themselves--and their CEOs--with lavish parties and golden parachutes, while they fail miserably and their employees are royally screwed. And, with the possible exception of John Walsh, no one has done more to pressure states to pass "Jessica's Law," in trying to better protect children from sexual predators. He really does see himself as a protector of the little guy, ironically just like Michael Moore does.
Bill O'Reilly reminds me of other hard-nosed, East-Coast, Catholic School-raised people I've known. He presents his opinions rather forcefully, and this sort of person tends to grate on me. Why? Because I was raised in a family environment where people offered their opinions more diplomatically. But what I've discovered about these guys? It's not that they expect the rest of us merely to accept their positions. On the contrary, they expect you to come to the table with yours too--just as forcefully, if you feel the way you do. They like a good scrap. About ten to twenty times per week, after making his assertions, he'll turn to a guest or two and say, "Okay, so where am I goin' wrong here?"
Do I disagree with his perspectives more often than not? Yes. But I do sense he is (at least) trying to be fair in uncovering facts and coming to conclusions.