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Olbermann - Week Of August 26

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Conan O’Brien’s Dartmouth commencement speech in 2011 sits in the highest echelon of addresses, along with Steve Jobs at Stanford and David Foster Wallace at Kenyon College. O’Brien was charming, hilarious, and honest while pandering to the somewhat neglected Ivy League audience—at least from the perspective of Harvard, Yale, and Princeton. But as he transitioned into the “big advice” portion of his speech, he reeled off one of the best moments of self-actualization in the face of mid-life upheaval I’ve ever heard, describing how late-night comedy got to the place it is at today.

“Way back in the 1940’s there was a very, very funny man named Jack Benny. He was a giant star and easily one of the greatest comedians of his generation. And a much younger man named Johnny Carson wanted very much to be Jack Benny. In some ways he was, but in many ways he wasn’t. He emulated Jack Benny, but his own quirks and mannerisms, along with a changing medium, pulled him in a different direction. And yet, his failure to completely become his hero made him the funniest person of his generation. David Letterman wanted to be Johnny Carson. And was not. And as a result my generation of comedians wanted to be David Letterman. And none of us are. My peers and I have all missed that mark in a thousand different ways. But the point is this: It is our failure to become our perceived ideal that ultimately defines us and makes us unique.”


This isn’t as clear-cut when looking outside of comedians. But what is clear with the benefit of hindsight is that Keith Olbermann dreamed of becoming Edward R. Murrow someday. And was not. He was one half of the dream team that put SportsCenter on the map, making a sports highlight show appointment television, cementing ESPN’s reputation as the Worldwide Leader In Sports, and paving the route for countless catchphrase-spouting highlight jockeys to imitate the comedy gold of Olbermann and Dan Patrick.

I watched Countdown every now and again, not nearly as often as I watched Rachel Maddow, so I can’t speak much about Olbermann’s increasingly radicalized political tack that led him right to the edge of a cliff, but the news that he would be returning to ESPN had me actually anticipating watching a new sports show (as opposed to Fox Sports 1, which continues to provide plentiful coverage without a depth of insight). ESPN could use some good press in the wake of severing their partnership with Frontline (which shares a studio with Olbermann’s new show), and an hour-long news program that improves upon shows like Rock Center and hopes to be a go-to for current sports news and in-depth commentary might be just what ESPN needs to salvage some of its reputation.


Olbermann is in a position to rebound from his high-profile departures over behind-the-scenes “difficulties” to synthesize his talents and his aspirations into a late-night sports commentary show. Olbermann is part highlight reel, part sports business commentary, part interview show, all revolving around the man who left sports for politics, to be a serious television newsman. His ego and fiery temper are legendary. ESPN put him in Times Square to keep him away from Bristol, which is just fine for Olbermann as well, since he’s a bit of a lone wolf. But after only five shows, Olbermann should be happy to find a place where he belongs, where he could quietly become the most sophisticated and intelligent show on a network bereft of successful shows that deal in the smart nitty-gritty details of sports, entertainment, and the members of the media who cover all of that.

It started on Monday with sound effects like the rejected bumper noise from Wii Sports as recorded by a ballpark organist and Olbermann speaking in media res, with “As I was saying…” As he did frequently on Countdown, Olberman begins each show by unleashing a monologue on a topic that ignites his fury. If the guy could tone down his impression of the part of Will McAvoy based on him and instead lean toward the parts of his persona that inspired Dan Rydell on Sports Night, he could hit an eminently watchable sweet spot.


The initial discussions on Olbermann lucked out with some easily-skewered issues. Fellow unlikely returning ESPN analyst Jason Whitlock was the debut guest, talking about media coverage of a Marc Sanchez injury during the fourth quarter of an NFL preseason game. The two discuss story invention instead of reporting—and discerning viewers can read between the lines to hear the commentary on the practices of that very network. This is the kind of subtlety Olbermann will have to employ when talking about his corporate overlords. And talking to Tony Kornheiser (awake close to midnight for the first time in decades, most likely), he leads a lively and informative discussion of whether college athletes should be paid, noting that athletes are severely undercompensated for what they bring in for conferences.

On Thursday night he opened with a beautiful, haunting (and self-promoting) 11-minute monologue about former New York Giants running back Doug Kotar, his death from a brain tumor, and what the 1973 labor negotiations between the NFL and the player’s union has to do with this week’s demonstrably lowball settlement for a chump change sum of $765 million paid out to former players and their families.


But then he brings on Jon Gruden—presumably already booked as a first-week high-profile guest before this story—who just might be the worst possible person to participate in this discussion. On Monday Night Football, Gruden is there to provide game film obsessive color commentary that is somehow different from Ron Jaworski drooling all over the “National Football League.” Gruden’s detailed analysis of player tendencies with draft prospects serves a purpose, and he clearly knows the inner workings of the game (though not as well as NBC’s Sunday Night Football team). But he’s not the big-idea thinker, nor the guy willing to say anything against the game that got him a Super Bowl and a plum gig with ESPN. It’s a mismatch of commentator and subject, making Gruden appear flustered before the interview shifts to other topics.

The first week even gets a chance to show why it’s so necessary for Olbermann to be a nightly program instead of a weekly show. Thursday, Olbermann talks about the NFL head trauma settlement, delivering his monologue about Kotar, but then Friday night he skewers the idiotic media responses to the case. One columnist says he should sue Pop Warner leagues and high schools seeking compensation, so egregious is the NFLPA fleecing the league—entirely ignoring the most frightening part of the settlement: that the NFL will not acknowledge what they knew about concussions or when they knew it. That’s the type of big corporation sidestep around actual, honorable responsibility that puts a professional sports league on the same level as oil companies and giant pharmaceutical firms.


Olberman’s director cuts between Pete Prisco’s asinine column for CBS and interviews with players who suffered concussions. I defy any logical, sane human to say the players don’t deserve medical compensation for the profits reaped by the league after that parallel montage. The opening statement is without a doubt the strongest and most consistent portion of the show, allowing Olbermann to indulge his sense of moral imperative but channel it through sports commentary to ease back on the gas.

Some of Olbermann’s go-to segments have sharp edges. The “Worst Person In Sports” rundown hits on some dumb things, but it makes Olbermann much meaner than his “Time Marches On” segment, which is like a condensed version of Tosh.0 as hosted by a sportscaster moonlighting as an uptight comedian. But the thrill of seeing him actually call sports highlights shows he’s still got it—that ease at whipping through a prompter like he’s just a guy dishing about the games while sitting with buddies on a couch.


Olberman is an insanely smart man, able to deliver even the cheesiest stories with such conviction that he imbues the information with power. Take his story about talking to his dying father about Satchel Paige in relation to Martin Luther King. It’s a heartfelt moment, a personal one, designed to make the audience sympathize with him, revere his intelligence at recalling all this information, and listen awestruck at the story of unwitting racism. “I was old enough to go to Yankee Stadium by myself and I was naïve enough to believe that Satchel Paige wanted to pitch for the Black Yankees instead. Amazing.” Olbermann still employs the self-aggrandizing streak that makes him appear like a pompous asshole, but at least he also looks like he’s having a ton of fun talking about sports again. He’s never as enthusiastic as he is during the cold open, but combining the serious capital-J “Journalism” with dumb Internet videos and actual sports highlights narrated by one of the best highlight hosts ever keeps the show from feeling too loose or too stuffy.

If his years away from ESPN—burning all his bridges at MSNBC and Current— have shown Olbermann that his puffed-up onscreen persona requires even a dash of humility, then Olbermann could grow into a must-see program for sports fans (or at least a must-listen podcast). As it stands, watching the first 10 minutes to listen to the prologue and hear about the guests is the best way to figure out whether to stick around for the full hour of this promising show.


Stray observations:

  • Damn, it is nice to hear “It’s deep…and I don’t think it’s playable” again.
  • If The Newsroom were just a shade more like Sports Night, it would be the perfect Aaron Sorkin show.
  • “This Week In Keith History” is a lovely bit of history and tongue-in-cheek self-deprecating humor.
  • Olbermann pulls punches when talking to Russell Wilson and Peyton Manning, but he does get great stuff out of Mark Cuban, always willing to reveal things about himself that perhaps he should keep closer to the vest.

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