I admit to having seen a few minutes of the Stewart schtick while stuck in hotel rooms. Stewart who was born with the name Leibowitz (funny he doesn't look Scottish) used to room with Anthony Weiner back in college. I think Weiner was the funny one. My sample size is small -- appropriate for Weiner and Stewart, and I'm not the target demographic, but I found Stewart tiresome in the same way that I find Sean Hannity, with whom I often agree, tiresome.
Both are equally predictable. Comedy works by being almost predictable. Except for pinata videos. Even there, though you know someone is going to get racked, you can't be sure exactly who, when and how -- so I guess it still holds. Stewart, like most of talk radio and most pundits, lacks even that much surprise. Again, maybe he was just going for the obvious on the few occasions that I watched. Maybe he was much more subtle and clever most of the time.
Greenfield doesn't think so:
Stewart wasn’t funny and knew little about politics. Unqualified to be in politics, journalism or even comedy, he straddled the line by casting himself as a critic of the media and politics. In his new role, he just had to be funny by the standards of politics and politically knowledge by the standard of comedians. It was a low bar that he just managed to limbo under. All he had to was to go after the right targets.
This is the tiresomeness of the talkers. They tell us what we want to hear. They mock what we want mocked. They say vaguely amusing things about people we dislike and so we laugh.
I'm generally credited with a mildly effective sense of humor. That is, I can usually pick up on the humor of something, and I will occasionally say something other people think is funny. For example, I was in a very distressing situation and state of mind recently. There is a certain member of the extended family whom my daughter-in-law dislikes, intensely. This family member was talking, texting, and fakebooking a lot of stupid, pointless stuff. My daughter-in-law was getting upset by it. A little short on temper that day, I let my frustration get the better of me, and said that the decisions in question would be made by those who knew what was going on and not by a drama queen. Actually, I added an expletive in front of drama queen. The daughter-in-law could not stop laughing.
It wasn't all that funny, but it skewered someone she wanted skewered, and it caught her by surprise, because, short of slamming a hammer down on my thumb, I don't say those kinds of words. Even then, I usually manage to moderate them if anyone is around.
This, though, is how people of very modest talent and intelligence, such as Stewart, Colbert, Al Franken, all the people on "Saturday Night Live", O'Reilly, Hannity, Levin, and even, to some extent, Limbaugh make a living. So long as these things are limited to talk shows and sketches, it is fairly harmless. When we move into other realms, the attitude is a lot more dangerous. Greenfield again:
Obama’s fake self-awareness made him seem authentic in a social media society composed of reflective levels of personality. .... [Obama] truly embraced politics without accountability, transforming every issue into a joke or referencing it back to his own biography.
While he may have come out on the stage with a unique personal story, what kept Obama competitive was his skill at refracting everything through layers of irony and self-awareness. His approach was to borrow Stewart’s own routine without any of its ambiguity. Stewart’s pretense of triangulation became Obama’s obsession with turning his radical left-wing politics into an imaginary middle ground.
We have lost the ability, so it seems, to have legitimate political discussions. Obama argues with caricatures of his opponents, while to argue with Obama is to argue with a caricature. It is as ineffective as trying to argue with Jon Stewart because all he is going to do is have the fake flower on his lapel squirt you in the face. People voted for Obama and elected him twice because they did not want a "serious" politician in the White House. Well, congratulations. You've sent in the clowns.