EPISODE 365: HOW TO ENJOY THINGS

Battleship Pretension says:

I see why you would compare the two, and Whittle’s half-British upbringing certainly isn’t doing him any favors as far as having a genial cadence, but I think the difference between the two men is about what they are promoting. Agree with him or not, Whittle is promoting his values and what he believes to be the correct course of action for the country. One can see this in his speeches, as he is quick to complement and defer to those that he considers to be more capable or knowledgeable than he is (like a Victor Davis Hanson or Thomas Sowell). He wants the audience to understand and embrace the political philosophy, no matter where they get it from. Certainly, he can get a bit snippy as he does so, which I don’t always like, but that is common in the pundit community.
Whereas I’ve always gotten the impression that Bill Maher has been less interested in promoting his viewpoint and more interested in promoting himself. He always seemed to me- whether in his stand-up, his television shows, or his movie- that he genuinely considered himself the smartest guy in the room, and wanted to make sure we all knew it, too. In this way, he reminds me of Armond White. Both men are (probably) sincere in their views, but the way they express those views seems to have more to do with setting themselves not merely apart from everybody else, but above them.
But, then, Maher and Whittle come from different backgrounds. As a comedian, it was important for Maher to be able to command a room in a very specific way. In many cases, he had to win people over. One of the ways to do that is to exhibit a great deal of self confidence, so the audience could think, “Man, we better listen to this guy. See how smart he is?” So it’s a bit more understandable to see how he arrived where he is.
With Whittle, however, whatever smugness may be there could lay in his becoming a public speaker solely as a function of politics. As such, he didn’t require as much to get the audience on his side, as they likely already agreed with him. So, the confidence could come from knowing that his audience was on his side no matter what. But, in the various Q&A sessions that I’ve watched, he always seems more than willing to admit when he doesn’t know something or at least doesn’t have an answer ready. I find this to be inherently humble, even if it doesn’t permeate his prepared remarks.
That was a long answer to your question, but there it is.