If there was one comedian/mid-level celebrity whose career I’d like to emulate it would probably be Michael Ian Black (okay, there’s a laundry list of comedian/mid-level celebrities who careers I’d like to emulate, and an even longer list of A-list celebrities whose resumes I wouldn’t mind having. But there are few people out there who I admire and appreciate at the level of Michael Ian Black. One of the reasons I like Mr. Black so much is because, obviously, he’s as funny and smart as anyone else out there (if his work in I ♥ the [Insert Decade] didn’t convince you of that, check out his stand-up album I Am A Wonderful Man, an excellent performance from someone who is not known as a stand-up comedian). But, beyond his humor, I especially appreciate the fact that he has the courage to say or write just about anything, the best examples of which are found on his Twitter feed, where he makes fun of everyone and everything from Asians to his kids to his wife cutting off the tip of her finger to himself. Often times I’ll find myself wanting to tweet something potentially offensive, and I don’t do so because I fear that not everyone will get the joke; sarcasm and satire sometimes don’t play so well in less than 140 characters. But Black has been able to pull that off, so much so that he’s participated in several Twitter fundraisers in which for a small donation he’ll make fun of you mercilessly, usually mocking your Twitter name or criticizing your photo. He has created this persona of being an arrogant, insensitive asshole (again, refer to the name of his comedy album), which is a weird achievement to want to replicate, but it seems clear to me that it’s just a put-on. It might be an extension of the real Michael Ian Black, but, if so, it’s a huge exaggeration. I mean, he lives in Connecticut with his wife and kids (who he appears to loathe, if his tweets are to be believed), so how terrible can he really be?
Amidst this backdrop of bombastic, often crude, tweets and blog posts it was surprising that Black received the most backlash for a tweet he composed on Friday night to commemorate Conan O’Brien’s last night as host of The Tonight Show:
Typical trenchant, insightful, slightly dickish Michael Ian Black commentary. But out of all his tweets this one caused the most commotion (although, as you can see, it was retweeted 100+ followers, so I guess not everyone was outraged). It was a joke, but like many of his jokes, he had a point, a good point. Which is another aspect of MIB I appreciate: his candor. He’s a fan of Conan too, but the truth is Conan fans didn’t turn out in droves until these last two weeks, when it didn’t matter anymore.
So, to clarify his point, Black knew he needed more words than Twitter would allow, so he took to his blog (and spared us from a full on tweet procession), and exemplified another quality I admire: intelligence. He composed his actual, and, as he noted, “unfunny” thoughts on the Conan situation, comparing Conan to Sally Fields in Norma Rae and asking “how did a Harvard-educated, multi-millionaire late night talk show host magically transmogrify into a guy who got laid off at the local car plant?” Now I’ve basically been glued to the computer the last two weeks reading every update on the late night wars and watching every relevant monologue the night before, and I’ve even contributed my own thoughts, but Black does have a point. In the end, it’s just millionaires playing in the sandbox, and Conan doesn’t really represent the oppressed, jobless masses. In his essay, Black puts aside the sarcasm and the deadpan humor, presenting refreshing clarity about the whole thing. I’m not sure I’ve read a better breakdown on the skirmish. Despite the working title of his latest TV show, Michael Ian Black does understand. A lot better than most of us.
Bonus: How I once gave Michael Ian Black unsolicited career advice. Sorry!
Do I want Jay Leno to have a show? No. I think his time has come and gone. When 
Jumped The Snark 