Wow, that side of O'Reilly makes me want to listen to him, not that I have the time. I also think TA is almost on the ball, except that it wouldn't be O'Reilly himself but the other Fox cast on their shows and guests who appear on his show. Plausible deniability is a nice thing.
The day after Super Tuesday 2008 I was in the process of a cross-country road trip; that particular day I drove from Amarillo, TX to some hovel south of Chicago. Now, being that I'd missed most of the primary shenanigans the day before (and that I was sick of my CD collection by that point anyway), I decided to check the radio for the breakdown.
Now, since I was listening to talk radio in God's Country, naturally all I was able to get were conservatives. Hey, any port in a storm; I'll just glean the facts from the spin and enjoy the rest for what it is, and then fact-check when I get to Michigan. No sweat.
Well, first of all, Laura Ingraham was hilariously distraught about Mike Huckabee somehow cockblocking Mitt Romney out of winning one primary, like that mattered or whatever. Michael Savage was equally histrionic but he is an Objectively Awful Person too so w/e Bl
Anyway, the point is I ended up listening to Bill O'Reilly's radio show for a while, and I have to admit I unironically enjoyed it. The guy is just hilariously egotistic and wastes absolutely no opportunity for self-promotion (my favorite was how he managed to segue from some state's primary results to his record on predicting Super Bowl results in under 15 seconds), but if you take that for what it is he actually sounds pretty fair if not always accurate.
One bit of his I liked was when he was talking about Obama being a liberal (maybe not accurate in hindsight but he was hardly alone in this appraisal in February of 2008), and then defined "liberal" as someone who believed in "using government power and resources to right wrongs"; he said he thought it was a totally defensible position, if not one he necessarily agreed with. I kind of liked that; might have not been exactly accurate but it was reasonably close for someone who disagrees with it, and sort of frames the policy debate for his listeners as "disagreement in judgment, not in character".
So yeah, as Fox pundits go O'Reilly is pretty okay when his ego isn't wounded. I think he's a little too insecure to make a living out of it but I could easily see him being That Conservative Guy at the Bar I Don't Hate. Out of anyone on Fox, I could see O'Reilly saying this and meaning it.