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I read Michael Miner's Hot Type this week, on the urgent humor deficit facing journalism, and daily newspapers in particular, with great interest.
I basically agree with it, although I think we're well past the point of crisis and that newspapers have given up on even trying to be funny (Maureen Dowd winning the Pulitzer was the flag of surrender). Even when I was growing up in the 80s and 90s it seemed we had a dearth of newspaper humor. I remember enjoying James Lileks, who was syndicated in my local paper, and of course Dave Barry during his prime, but the funniest stuff was in the comics pages--Doonesbury, Calvin & Hobbes, and my favorite, the inestimably great Bloom County, which was probably more topical than you remember (the series about Reagan's Star Wars initiative and the giant laser space frisbees is a classic). Now, reading newspapers is, to borrow a phrase, like watching old people eat. That goes double for Richard Roeper's column, which reads like that color you get when you mix all the paints together.
Honestly, I can't tell you why newspapers aren't funny. My guess is that it's because they're risk-adverse, and humor is the riskiest of content. Crappy op-eds and bad reporting aren't painful unless they're unusually bad; failing at humor is like scraping your nails on a chalkboard. (For what it's worth, I thought the Sun-Times's late Red Streak was the most entertaining new local publication in forever, and I suspect it was because it existed as a RedEye cock-block and had nothing to lose.)
Newspapers also tend to promote columnists, who have the most consistent opportunities to be funny, from the news-reporting ranks, and reporters aren't supposed to be funny. Since humor is a craft, and a difficult one, I suspect that reporters fall out of practice over the years.
And, of course, there's the Web. That's where virtually all the talented political and etc. humorists are working these days. A lot of great comedy is an acquired taste, and online you can acquire it at your leisure without worrying about whether some editor will tire of people waiting to get it. Also, there are a lot of technically proficient people on the Web, obviously, and in the field of visual comedy poor execution can destroy a good joke.
[Let's pause for a Handy Tip: Learn a photo editing program, and don't be above figuring out color balance, noise filters, and other functions. The Web is awash in badly cropped, amateurishly designed collage jokes which aren't funny. Being able to blend one picture into another is the visual equivalent of comic timing--as you can see here, I bollixed the color/noise/etc here because I was lazy and busy; also, I was too lazy to track down the right font. This was better but Lincoln's face isn't smooth enough. Ask a talented friend to help you, or better yet pick up a new skill.]
With that, a list of sources for humor, political and otherwise, on the Web (I have avoided some usual suspects):
* Chauncey Billups. Sadly defunct but still online (where the line above was borrowed from). This is what the Web was invented for. I suspect most editors would look at this like it was blogged from Mars, and it took me awhile to get addicted to it. I have never checked a blog so frequently for infrequent updates. Gabe Said We're Into Movements, from the same author, is less funny, more elegiac, but no less perfect.
* Achewood. Achewood is the best thing. I know that may be obvious at this point but it bears repeating. Achewood is another thing you have to read for awhile before it clicks.
From the latter: "I would say that screwing his secretary is his main achievement since taking office, and one of the things that sets him apart from monomaniacs and cyborgs like Blair, Brown and Straw. Blair would no more fuck his secretary than he would read a novel. Why? Because he’s a lunatic and a freak, with no more sense of proportion than a Saudi cleric."
I'd give my left arm to have written that. I don't even care whether or not it's accurate; it's just so perfectly composed.
* The Bugle, from John Oliver (The Daily Show) and Andy Zaltzman. Actually, this is a not-quite-as-great alternative to their old BBC radio show The Department, which I still can't find a legal copy of. But it can be had.
* Alicublog. Even when it's shooting fish in a barrel the prose is so wonderful that it's worth it. "Follow that paragraph around the block and you'll see that it's trying to shake you." "You could try to explain that these cows are very small, while those cows are far away." I started watching Father Ted because of that post.
* Matt Taibbi, Rolling Stone. The new P.J. O'Rourke (by the way, you cannot go wrong with Parliament of Whores and Holidays in Hell, both master classes in humor writing). His obit of Boris Yeltsin reminds me of Hunter S. Thompson's elegy for Richard Nixon.