Keith Olbermann at Chik-Fil-A

L’enfant terrible sportscaster and firebrand political pundit Keith Olbermann has a long history of fostering turbulent work environments. Bob Ley, Olbermann’s one-time coworker at ESPN, is quoted in the 2011 ESPN history Those Guys Have All the Fun as saying: “We felt not so much relief when Keith left as unrestrained fucking joy.” Olbermann has since gone on to work for, revitalize, and ultimately alienate places like Fox Sports, MSNBC, and Al Gore’s Current TV.  The media landscape is fairly littered with victims of Olbermann’s acerbic wit, undeniable charisma, and correspondingly large ego. After a long stretch in the wilderness, Keith is back where he belongs, with his own show on ESPN2, providing the smartest sports commentary in the business. (Granted, talking-head buffoons like Skip Bayless have set the bar pretty low.) That being said, history suggests it’s only a matter of time before he gets restless and starts erupting. Below are ten suggestions for Keith’s next professional endeavor once he’s shown the door (again) at ESPN.

Chick-fil-A drive-thru attendant: Noted delicious chicken sandwich maker Chick-fil-A made waves last year when the company’s COO, Dan Cathy, loudly and publicly opposed gay marriage. Liberal backlash predictably followed, which was, in turn, followed by the counter-backlash in the form of “Chick-fil-A Appreciation Day,” where thousands turned out at “restaurants” across the nation to show support for Cathy’s right to express his homophobia under the First Amendment. Putting Olbermann at the window—complete with ill-fitting polo shirt and “Hi my name is Keith!” name tag—as hordes of anti-gay marriage (sorry, “pro free speech advocates”) drive up to him and order their 1,500 calorie-lunches, and you have ready-made, must-watch television.

I refuse to believe Olbermann wouldn’t greatly enjoy handing out parking citations right as the meter expires.

SAT tutor: “Listen kid. Forget reading comprehension and all of that other horse shit. Here’s the only question you need to know the answer to: Who is the worst person in the world? Is it, A) Donald Trump, B) Bill O’Reilly, C) Karl Rove, or D) Al Gore? Trick question. It’s my as-of-this-second former agent, for getting me this craptastic gig.”

Parking meter maid: I refuse to believe that Olbermann isn’t a man who would greatly enjoy handing out parking citations right as the meter expires. Refuse.

Bristol Tour Bus Guide: ESPN began its broadcasting life in Bristol, Connecticut, which is still the fortress of solitude for the worldwide leader in sports. One of Olbermann’s first public spats with his once and future employers occurred when he made an unauthorized appearance on The Daily Show (then hosted by ESPN alum Craig Kilborn) and compounded the offense by referring to Bristol, on air, as a “godforsaken place.” A licensed, double-decker bus tour of Bristol, with Olbermann on a megaphone, pointing out local hotspots where tourists could hear the mirthless laugh of the Bristol damned, would be a sure-fire moneymaker.

Dentist: Have you seen this man’s teeth? Immaculate.

Keith Olbermann as Batman

The New Batman: When Ben Affleck was tabbed to play Batman in the next Superman movie, the Internet flared up in an uncontrollable conflagration of fan-boy outrage (as of this writing, a petition on to remove Affleck from the film is at 87%). But if Affleck was removed, who would replace him? My vote is for, you guessed it, Keith Olbermann. Sure he’d be a slightly grayer Bruce Wayne, but what he lacks in brawn, youthful sidekicks, and world class martial arts training he makes up for in good hair, superpowered zingers, and a wide range of aggrieved nemeses.

Huffington Post blogger: Sure, HuffPo’s celebrity bloggers—your Alec Baldwins, your Kirk Douglases (who, incidentally, could still play a kick ass Batman at 96), your National Entertainment Journalism Award-winning James Francos—use the platform as a means to get out their super-important opinions about wars and Wall Street and poverty and stuff, but this would be strictly a last resort for Olbermann. The pay cut alone—two million a year, his reported salary at ESPN2, to zero, HuffPo’s going blogging rate—would seem to be a sticking point. More importantly, Olbermann would no doubt chafe at his incisive political commentary being run next to stories about Lindsay Lohan’s “seriously short shorts” or a heartmelting friendship between a piglet and floppy-earred rabbit.

Keith Olbermann, marriage counselor

Marriage Counselor: Who but Keith better understands the gentle art of mercilessly picking people apart? (He infamously once caused ESPN colleague Suzy Kolber to lock herself in the bathroom and cry.) In one intense, hour-long session, a married couple would go from hating each other’s guts to despising Keith instead. By transferring all of that anger onto his broad shoulders, the troubled couple will quickly be on the road to rediscovering marital bliss.

Netflix Original Buddy Comedy with Corey Feldman: I feel like this union could work on a number of levels. First of all, Feldman has been missing a sidekick since Corey Haim tragically died in 2010, and Olbermann hasn’t had a worthy wingman since his days of doing SportsCenter with Dan Patrick. Secondly, Feldman could really teach the dyspeptic Olbermann some valuable lessons when it comes to loosening up. Finally, and perhaps most importantly, Corey knows better than anyone the keys to reinventing oneself after serious career setbacks. Two words: Olbermann’s Angels.

Men’s Warehouse Spokesperson: “You’ll look stupid. I guarantee it. What do you mean that’s not the tag line? No, I’m not going to read a goddamn teleprompter for a goddamn commercial. I have to tell you guys, this is the fucking minor leagues of men’s formal wear. Tell my agent to get Brooks Brothers on the phone. It’s goddamn double-breasted amateur hour over here.”


Photo illustrations by Sarah Mulligan.