Olbermann is a wisecracking sportscaster-turned-wisecracking political pundit and left-leaning counterweight to his Fox News opponent Bill O'Reilly.

So—Karl Rove is going to be a Fox News contributer! What an exciting and unexpected move. We hope it goes well for them! It probably won't, though. Because Karl Rove, that Machiavellian Boy Genius, is terrible on-air and also not even particularly adept at analyzing politics. He's a great smear campaigner, sure! But he's not even Lee Atwater's equal in that dubious regard. The man micromanaged one of the least popular presidencies of the last hundred years, parlayed untold goodwill and love into worldwide scorn, and also lost two of Bush's most important elections. Namely the 2006 midterms and, oh right, Bush's initial election itself. The only people who still think Karl Rove is some sort of brilliant political mind are semi-literate Kos commenters. And Roger Ailes, apparently. Even Keith Olbermann thinks Karl is only the third worst person in the world! See for yourself, after the jump.

Playboy editor Chip Rowe would like you to know that he didn't actually solicit a pro-Olbermann letter from an Olbermann fan blogger after receiving a flood of negative responses to their interview. He merely invited her to respond if she so desired. Also this is S.O.P. and also "I read it for the articles" jokes are not funny anymore. [Playboy]

In the October Playboy, Keith Olbermann called Fox News "worse than Al Qaeda." The letters page in this month's Playboy "is littered with negative reaction to the Olbermann interview," according to TVNewser. Except for the positive one Playboy editor Chip Rowe solicited from the lady who runs an Olbermann fan site! The letter's author blogged about it, possibly unaware that she was embarrassing the respected titty mag. [BloggingOlbermann.com via TVNewser]

The latest issue of Men's Journal tells the story of Keith Olbermann, the logorrheic sportscaster who terrorized ESPN while creating its sarcastic brand, became a failed "serious" newscaster, and finally ended up as the hopeful savior of perennial third-place cable news network MSNBC by providing a liberal blowhardy-but-funny alternative to Fox's self-serious conservative goons. Olbermann—nearly canceled a few short years ago—is rapidly becoming the face of the network, thanks to his solid ratings and fantastic demographic numbers. "Keith runs MSNBC," an unnamed senior MSNBC executive tells Men's Journal. "Chris Matthews is infuriated by it." Naturally! They're both ridiculously self-important, convinced of their encyclopedic knowledge of everything political, and they tend to not mesh well with other egos. Poor Chris already has Tim Russert undermining him, the last thing he needed was an up-and-comer usurping his tiny, wonky niche. [TVNewser]

We all know by now that Tom Cruise and Katie Holmes are the most awkward couple in Hollywood, if not the entire world. Last night, Keith Olbermann proves that he too reads InStyle magazine and that he couldn't get enough of their nutty Katie Holmes interview this week. In it, she says that Tom thinks it's hot when she has a security detail. Olbermann and Best Week Ever's Paul F. Tompkins think that this tactic isn't exactly the best way to a woman's heart. (They are correct!)

Keith Olbermann, host of MSNBC's "Countdown," looks at the Wikipedia Scanner episode, in which a website made it vastly easier to trace edits made to the online encyclopedia back to the organizations that made them. He notes that two News Corp.-owned media properties — the Times of London and Fox News — reported on the scandal without noting their own, er, contributions to Wikipedia. Fair enough. But, then again, did Olbermann note any edits made by his colleagues at NBC?

While the rest of us are drinking and snoozing, the television is trying to transmit important information into our homes. Today, our special correspondent for T.V. punditry catches us up on the week in chat shows. Because we totally wouldn't watch that shit if you paid us. Get your tinfoil hats on!

Never let it be said that MSNBC's Keith Olbermann is myopic. The anchor of Countdown just sprung for a 4.2 million dollar condo at 200 E. 69th St, a hulking Trump tower, says the Observer. Whilst padding about in his Missioni housecoat through his five 40th-floor rooms, Olbermann will enjoy 360 degree views. The same can't be said for Fox News's late-night host Greg Gutfeld, who recently bought a coop in a tiny 5-story building on W. 49th Street for an infinitesimal fraction of the price of Olbermann's condo. But what his apartment lacks in size is made up for with convenience—News Corp is located just around the corner on 48th and 6th, close enough to stumble home from after another soul-crushing night of broadcasting to stoners. Take that, Olbermann! —Josh

• Southampton Press, owned by entirely nutty Joseph Louchheim, begets East Hampton Press; East Hampton Star not thrilled. We say: If there are two places to read crime reports about dumb girls named Amy Kline who miss the last train back to the city and call the police, who then actually call and get them a bus back to town instead of telling them to sleep on the street, we're thrilled. [NYT]
  

• Comedy Central and TVLand head downtown to Hudson Street, although that may just be a plot by Viacom to make mass layoffs easier to handle. [NYP]
  

• Wall Street Journal Managing Editor Paul Steiger set to retire at the end of next year. [NYP]
  

Page Six continues its bizarre feud with Keith Olbermann, today reporting that Olbermann, "who's been branded lousy in the sack, apparently doesn't want his viewers to suffer the same sad fate. The MSNBC loudmouth has started running commercials for erection-enhancing drug Cialis on his 'Countdown with Keith Olbermann.'"

• Larry Page and Sergey Brin pretend that they're playing with real money. [NYT]
• "It's generally a questionable sign when a publisher flees before a magazine publishes its first issue; it's worse when the magazine has been launched and failed twice already." WWD harshes out on Radar, compensates by running "thin" picture of Maer Roshan. [WWD]
• Keith Olbermann makes obscure reference to the time Nicole Richie took a gigantic crap in Paris Hilton's mouth in an epic game of Truth or Dare gone awry. [FBNY]
• The problem with new media? Not enough people getting killed. [LAT]
• "Maybe if you want to get a younger audience for your newscast, maybe you could start by not ash-canning a pregnant 43-year-old woman and replacing her with a man 20 years older. I'm just thinking out loud here." We would have said "shit-canning," but otherwise James Poniewozik speaks for us. [Tuned In]

• Paris Hilton and Nicole Richie just might have called a truce, as the two dined together at a steakhouse last night. Figures Paris would take Nicole to someplace with food, where Paris could back her into a corner with all sorts of caloric manipulation and threats. It's like having a sitdown with Superman in a room full of kryptonite. [TMZ]
• Okay, so maybe Madonna did adopt a Malawian boy, despite her publicist's denials. UK rag The People says that if the boy exists, his name his Luca. And he lives on the seventh floor. [Page Six]
• Is Penelope Cruz a lesbian? If so, it might explain her willingness to work as Hollywood's most popular beard. [R&M]
• Four months after the fact, Page Six learns of Keith Olbermann's ex-lover's blog. [Page Six]
• It doesn't matter how much you pay Lindsay Lohan — if she's hungover, she's not going to show at your event. [SMH]
• For his final column, Lloyd Grove goes out with a bang: Horace Mann students use their Facebook profiles to write mean things about their teachers. Sigh. We're gonna miss you, buddy. [Lowdown]

Professional Bush-hater Keith Olbermann recently received an envelope full of white powder. The Post reports:

There are many ways to go about ridiculing Fox News screambox Bill O'Reilly. If you're mouthy, you can shout "Shut up!" at every given opportunity. If you're crafty, you can distribute personalized falafel loofahs as holiday gifts, as did the Smoking Gun in 2004. If you're enterprising, you can even start your own satirical spin-off on Comedy Central. All are perfectly acceptible ways of deriding a man who seems to have been sent from above solely for the sake of mockery. Hell, if you're lazy, you can even just don an O'Reilly mask and do a stupid dance. You cannot, however, don an O'Reilly mask and do a Nazi salute. MSNBC host Keith Olbermann tried it this weekend, and the humor just got overshadowed by that whole systematic extermination thing.

How did Keith Olbermann's MSNBC show cover the White House flip-flop scandal? (Which, interestingly, is not a scandal about Bush's now-void promise to fire any staffer involved in the Plame leak, but rather is a kerfuffle over several members of Northwestern's NCAA-champion women's lacrosse team, who wore flip-flops on a White House visit.) "By inviting Mo Rocca on the show last night for an on-air fashion demonstration," answers Jossip, who kindly provides a screen shot.