There is a whole style of comic performance and writing that relies on snark, on archness. It is comic hipness. I won’t try to trace its history, but it includes Carlin more than Cosby, Newhart, or Pryor. You could sense it in Carson and Leno, but it is Letterman’s stock-in-trade. SNL seems to have retained the joys of silliness through its many incarnations, but the attitude of superiority has never been far below their surface. Al Franken breathed it. Monty Python, very little archness. There’s a touch in Steve Martin, and not so much as you’d think in Bill Murray or Will Smith. Very little in Robin Williams.
I must have liked it fairly well over the years – PJ O’Rourke has got plenty, Bryson moved increasingly in that direction. The tone is there in Dave Barry, in Garrison Keillor. But I find it quite tiring and irritating these days. That raising of the eyebrows and looking toward the audience with amusement at how stupid, how gauche, the particular object of ridicule is now provokes a desire to punch their slightly-lifted noses. Except if they can still laugh at themselves.
I have noted how much I value the ability to laugh at oneself as a measure of emotional health. I think some of that is in play here. Rick Reilly used to be able to laugh at himself, and was funny. Now he can’t and he sucks. Bill Simmons still can, for the time being. Barry laughs at himself easily; Keillor can laugh at his young self but less so at his adult self; O’Rourke can still skewer himself (though perhaps less…?), Bryson is a mixed bag on this and always has been. If you go back over the entries in the first paragraph, the pattern holds pretty strongly: those who can self-mock stay funny. Trudeau and Breathed started by being able to laugh at themselves, then lost this. Scott Adams’s pounding on the stupidity and meanness of management worked when Dilbert and Wally’s foibles were also a main focus. As that went, and they became only the hapless everyman observers of the lunacy, Dilbert became less funny.
Ben reads Chuck Klosterman and David Sedaris. I can tell they have this snarky humor - it may be the humor of the era, growing up slowly in the 70's, establishing dominance in the 90's. It is certainly the humor of the reader more than the viewer. I don't know if either of them have the ability to send themselves up, but I'm pretty sure that would be the dividing line whether I liked them.
Update 2011: Wow. I hadn't realised it had gotten this bad. I sense a Firesign Theater reunion right around the corner. So topical, so now!
Update 2019. I had not included the late-night TV hosts in my original essay, but I think it applies to them as well. I am not especially knowledgeable about the topic, but it is my impression that they started off being able to laugh at themselves but have become less able to over the years.