By David Dudley
Photograph by John Abbott

Keith Olbermann's well-tuned sense of outrage has made him an unlikely hero for a skeptical age.

As a sportscaster for Ithaca's WVBR, the student-run FM radio station, a teenage Keith Olbermann '79 was prone to irreverence. On pleasant days he'd haul his microphone outside the station's Linden Avenue headquarters and broadcast in the sunshine. Once he did the sports in rhyme. He'd been reading a lot of Ring Lardner and was inspired to compose a two-and-a-half minute sportscast in verse, just as the legendary newspaperman had done as a beat reporter covering a Cubs-Giants rainout in 1910. After wrapping the bit, Olbermann walked into the control room, where he found the station engineer getting off the phone. "Somebody just called in," the engineer announced, "and asked me, ‘Is this guy a jackass, or what?'"

Olbermann chuckles at the memory. "It wasn't a rhetorical question," he says. "The guy was really trying to find out if I was thought of as a jackass, or if there was some other explanation."

This is an issue of ongoing resonance with current Olbermann watchers, some of whom wrestle with the same question as they tune in to his nightly MSNBC newsmagazine, "Countdown with Keith Olbermann." In the past two years, the former ESPN anchor has assumed a polarizing role as an outspoken liberal voice amid the right-leaning talkers on cable news. The position comes with all the glory and infamy of digital-age punditry: video clips of his speeches assailing the Bush Administration ranked among the most popular blog links of 2006 and have raised Olbermann's profile in antiwar circles. Some network execs and industry critics tracking the show's rising ratings and pop-culture cachet have suggested that "Countdown," with its brisk mix of serious policy discussion, tabloid whimsy, and unabashed commentary, is nothing less than the network news of the future. "The most compelling news personality of his generation," the Hollywood Reporter recently proclaimed. "Love him or hate him, he is a charismatic, righteously indignant force of nature who is inspiring fervent cheers and detesting jeers in equal measure."

Accordingly, the nation's red precincts now echo with attacks on all things Olbermann: his opinion-laced style, his seriocomic feud with Fox News rival Bill O'Reilly, his history of workplace disgruntlement, his dating habits. In November, a frequent poster to a conservative Web forum was arrested by the FBI for mailing threatening letters laced with a harmless white powder to several media personalities with perceived left-of-center tendencies, Olbermann included. In January, Geraldo Rivera threatened to "make a pizza out of him." In other words, the former local sportscaster with the Guy Smiley looks has officially joined Michael Moore and Al Franken on the Liberal Media A-list.

This seems to suit Olbermann fine. Arriving for a late breakfast at Manhattan's Parker Meridien Hotel, Olbermann is buzzing over the latest from the Fox camp--O'Reilly's charge that NBC itself is "an activist network" that had gone "sharply to the left." The previous morning, NBC News president Steve Capus told reporters that O'Reilly--who pointedly refrains from mentioning Olbermann by name--had a more specific target in mind. "I don't quite understand it, "Capus said. "I assume it's because Keith Olbermann has had such tremendous growth and there's real momentum behind Keith's broadcast." This in turn has handed Olbermann yet another opportunity to berate his bête noire, and he's a contented man.

"People think I'm really bothered by all the criticism," he says, sipping a strawberry smoothie. He tells a story about being rebuffed by a fan at Shea Stadium in April 2003, right after "Countdown" debuted. "The guy tells his friend, ‘Never mind him--he's a liberal.' Now, I've been on the air a week and a half. All we'd done at that point is introduce reporters from the field in Iraq. No commentary, no criticism, no point-of-view. And yet, this word had become like a sign. So we're starting with the point that, because someone perceives me--incompletely, if not incorrectly -- as a liberal, they're going to dismiss me utterly. Somehow they think that will limit me. I think it liberates me."

As befits a man who has been doing radio since high school, there is little dead air during a conversation with Keith Olbermann. He's an unlined forty-eight years old, six-three and possessed of camera-ready gravitas: his jet-black helmet of anchorman hair has assumed a dignified pewter cast, the 1980s moustache of the KTLA years is long gone, and he chats in the dulcet baritone of a born broadcaster. On "Countdown," when he needles O'Reilly by quoting the Fox host's own words, he takes his voice down a notch and assumes the stentorian tones of Ted Baxter, fatuous anchor of the "Mary Tyler Moore Show." But the joke is that this sounds little like O'Reilly, who has a plainspoken, I'm-Just-Saying cadence to even his most immoderate pronouncements. It just sounds like Olbermann, only more so.

The voice is deployed to its most striking effect when he delivers a "Special Comment," an op-ed monologue that closes the show occasionally ("whenever my blood rises to a sufficient height," Olbermann says). The first, inspired by the woeful official response to Hurricane Katrina, ran in September 2005, and its memorable charge that the government "has just proved that it cannot save its citizens from a biological weapon called standing water" was so well received that MSNBC execs asked for more. Olbermann demurred. "It has to be organic," he says. "I viewed it as an isolated incident."

The Special Comment would not re-emerge until August 2006, with an epic denunciation of then-Defense Secretary Donald Rumsfeld, who had just compared critics of the war in Iraq to appeasement-minded politicians of pre-World War II Europe. "Thus did Mr. Rumsfeld make an apt historical analogy," Olbermann began, "excepting the fact that he has the battery plugged in backwards. His government, absolute and exclusive in its knowledge, is not the modern version of the one which stood up to the Nazis. It is the modern version of the government of Neville Chamberlain."He closed with a McCarthy-era quotation from his broadcasting idol, Edward R. Murrow. Less than two weeks later he excoriated the Bush Administration on the fifth anniversary of 9/11. Clips of those two speeches, posted to YouTube and several political websites, have been downloaded hundreds of thousands of times, making "Countdown" a multiplatform phenomenon.

Despite the newfangled distribution technology, there's something distinctly retro about the performance: a man in a suit, eyes locked on the audience, aiming ten minutes of well-modulated spleen at an unmoving camera. The essays bristle with literary references, ornate locution, and a barely contained sense of cosmic indignation. Associations with CBS newsman Murrow are both inevitable and intentional--more so since Olbermann began borrowing Murrow's sign-off, "Good night, and good luck." But a more frequent point of comparison is a fictional one: Howard Beale, the old-school anchorman prone to on-air meltdowns in the 1976 film Network. "You could do worse, "Olbermann says of his two journalistic models; a fan of the movie, he posed as a pajama-clad Beale for GQ's 2006 Men of the Year issue. "I can tell you that when I did that [Rumsfeld commentary], I felt like I was going to get up out of the chair and grab the camera and go, ‘Are you listening to me?' "At this, the voice assumes full Special Comment intensity, a swelling tide of outrage. "Did you hear how little he understands of the history he pretends to be a master of? That he thinks he would have been Churchill when in fact he's clearly Chamberlain? And, oh, by the way, it was his party in this country that appeased Hitler! It was his party that didn't want to get involved in the Second World War!" He cuts himself short and returns to his smoothie. "Anyway, I'm doing it again."

The peculiar thing about the current incarnation of Keith Olbermann as truth-telling Last Angry Man is that he first found fame as the smart-aleck who refused to take anything seriously. With his "SportsCenter" partner Dan Patrick on ESPN in the 1990s, he turned the staid highlight show into a postmodern playground of catch phrases and absurdist ad-libs. It was a style Olbermann had been honing for a long time. "What you saw on ‘SportsCenter,' that's what he did on his sportscasts on WVBR," says Peter Schacknow '78, who worked the news desk at the student station. A former business anchor on Bloomberg radio, he's now a CNBC producer." Keith already had this professional-quality broadcast voice."

Olbermann grew up in the prosperous Westchester County suburb of Tarrytown, New York. At eight years old, he got his first pack of baseball cards; within a few years, he was writing and performing his own sportscasts, first to himself and then via a high school radio station. "It opened up for me like a jewel that you find in the street," he says. At fourteen he wrote and privately published a book on major-league baseball coaches. At sixteen, when he arrived at Cornell, he had a sideline writing baseball card copy and editing a sports-card collectors' magazine. (Olbermann remains a rabid memorabilia collector, with a stash of cards covering every year from 1863.)

By the time he found his way to WVBR, Olbermann had a healthy head start on his colleagues. "The fact that I was sixteen and on a radio station was something I expected of myself," he says. "The older students were kind of surprised at my preparation. But I had done this before, so they put me on quickly." Olbermann first broadcast on October 7, 1975. "I came back to my room in Mennen Hall and played the tape of it that my neighbor had recorded," he says. "And realized that I mispronounced my own name." The lesson proved instructive: Olbermann became a methodical archivist of his own work and has since filled a rented storage space with tapes of his broadcasts.

Coursework took a backseat to radio work. With the Yankees a perennial contender, Olbermann's autumns were full of skipped classes and flights to New York to cover World Series games. "I was prioritizing," he says. "I never heard anybody in broadcasting say that their grade-point average ever figured in to whether they got work." At WVBR, where he quickly became sports director, he sold advertising, trained recruits, learned how to report breaking news, and dueled with pro rivals for listeners. "Keith was singlehandedly trying to turn the sports department into something," says Jim Savitt '80, a freshman sportscaster recruited by Olbermann. "It was an intellectually exciting place to be. We were trying to learn the business, trying to assert our adulthood. Keith had opinions on everything, and he had a way of articulating them in such a way that you were never really sure whether he knew what he was talking about."

In those post-Watergate years, the student broadcasters tended to obsess over careers, not politics. "They didn't call it the ‘Me Decade' for nothing," says Schacknow. Once, in a rare moment of self-doubt, Olbermann wondered aloud if he would make it. "He asked me, ‘Are we fooling ourselves?'" Schacknow recalls. "‘Are we good enough?' And I said, ‘Well, I know you are.'"

The ink was barely dry on Olbermann's diploma when he was hired by UPI in New York City. In 1981, he went to television, joining a new cable news network called CNN, then did local TV sports in Boston and Los Angeles. ESPN came calling in 1992, and the arch, self-referential banter Olbermann pioneered with Patrick on "SportsCenter" seemed to reinvent the genre overnight, paving the way for an army of imitators. It also made Olbermann one of the most famous sportscasters in America.

In a self-lacerating 2002 essay for Salon called "ESPN: Mea Culpa," Olbermann shed some light on his turbulent 1997 exit from "SportsCenter." "I couldn't handle the pressure of working in daily long-form television," he declared, "and what was worse, I didn't know I couldn't handle it." The details were more complicated: Olbermann publicly tweaked the network and its executives and gave some brutal assessments of former colleagues to the author of a behind-the-scenes book. As ESPN's director of communications, Mike Soltys, memorably told USA Today, Olbermann "didn't burn bridges here--he napalmed them."

The publicity saddled Olbermann with a reputation as a difficult co-worker, a perfectionist and prima donna who could be his own worst enemy. In 1998, that image only sharpened. Handed an opportunity to do a newsmagazine for MSNBC, "The Big Show," he quickly found the program consumed by the mushrooming Clinton impeachment scandal. The show was renamed "White House in Crisis," and, after seventeen months and an unsuccessful effort to broaden it beyond l'affaire Lewinsky, Olbermann wanted out. He found a very public outlet for his frustration: a convocation speech for the Class of 1998 in Barton Hall. "There are days now when my line of work makes me ashamed, makes me depressed, makes me cry, "Olbermann told the assembled graduates. The speech helped seal his fate at the network. "I remember, as I was writing it, that I had no inclination whatsoever to hold anything back," he says.

Mulling a more permanent return to campus, Olbermann spoke to a Cornell administrator about teaching in the communication department. Instead, he was traded away like a moody power hitter: NBC sold his contract to Fox Sports. "That's when you start thinking, Well, teaching at Cornell is noble and really a nice sort of symmetry," he says, "but that's eight million dollars."

His tenure at Fox was remunerative but no happier; two and a half years later, his low-rated weekly sports show was off the air, and a few industry prognosticators sensed the end of his TV career. "The sad truth is that Olbermann's perfect format was ESPN's ‘SportsCenter,' " Sports Illustrated mused in 2001, calling him "a supremely talented but restless soul who has worn out a string of welcome mats. . . . Olbermann will probably spend the rest of his career trying to recapture what he had with Patrick."

The door of Olbermann's office at the MSNBC studios in Secaucus is decorated with a few telling artifacts of his new station in life. Next to a picture of Kent Brockman, cartoon anchorman of "The Simpsons," there's an Olbermann trading card, trimmed in blue, with his team affiliation ("Liberal"). And there's a chummy snapshot of him with a beaming Bill Clinton, who asked Olbermann to attend the first meeting of his Clinton Global Initiative in September. "I've had fans among political figures before, "Olbermann says. "But I hadn't been invited to those things until the Special Comments occurred. It's interesting. It's also useful to remember that bandwagons leave every quarter hour in politics."

The journey back to prime time began with a gig as a substitute host on MSNBC in 2003. The shows went well, and the perennial third-place cable news network agreed to give Olbermann another shot. The premiere of "Countdown" neatly coincided with the invasion of Iraq, but it took time for Olbermann's innate skepticism to seep to the surface. "At the beginning, there was not going to be any commentary, and there was certainly not going to be any political stance," he says. "It was supposed to be an attempt to take a news format and make good television without sacrificing journalism. In an age of specialization, we'd be generalists. We have everybody on there, from John Dean to Lindsay Lohan."

Critics often call "Countdown" a left-wing approximation of the fire-breathing Fox News formula, but it's an inexact match: Olbermann's interview segments are typically civil exchanges with a repertory of journalists or like-minded experts, not O'Reilly-style shout-downs. The show's focus on the manifold failures of the Bush Administration, Olbermann contends, isn't an ideological crusade but an overdue application of journalistic incredulity. "On 9/11, the people who would have been skeptical of the president of the United States--the media and the opposing political party--suspended those skepticisms, for extraordinarily patriotic reasons," he says. "The administration believed that was some sort of permanent arrangement. And the last two years it's been necessary to disabuse them of this, in the strongest possible terms."

As support for the war wanes, Olbermann has the zeitgeist on his side. "Countdown" is now MSNBC's highest-rated program, and while his numbers lag well behind his time-slot rival O'Reilly, Olbermann has tightened his grip on second place, especially among younger viewers. All of which makes life pleasant in Secaucus these days, a state of grace that stands in marked contrast to Olbermann's previous employment situations. "Everybody loves Keith, loves the show," says executive producer Isabelle Povich '89. Rumors of friction with executives over Olbermann's anti-Bush rants occasionally rustle the blogosphere, but Povich dismisses them. "Those are conspiracy theorists. It's more like, ‘What are you guys doing that we should be doing too?' They've been incredibly supportive."

The question then becomes: How long can Keith stay angry? Povich notes that, while the Special Comments drive the buzz, they are a small and still-infrequent component of the show, much of which covers matters of less geopolitical import: celebrity tantrums, weird video clips, car chases. "Keith and I respectfully disagree about that," she says. "I'm the pop culture person. He thinks I'm crazy. But, you know, at a party you're not always going to talk about the war. You're also going to talk about ‘American Idol.' Our job is to give the right mix."

That mix--a curious aggregate of hard and soft news--may reflect lessons learned from Olbermann's previous MSNBC outing. Still, many ask what the White House's most determined mainstream broadcast critic will do with his nightly sixty minutes when the current occupant leaves office. "You do wonder how he's going to be able to shift gears," says National Public Radio media correspondent David Folkenflik '91. "It's hard to sustain that degree of outrage day after day. But smart people can play a lot of roles, and Olbermann is smarter than a lot of guys."

His foes, meanwhile, can take solace in his employment history and await the inevitable blow-up with management. So far, publicity brushfires have been largely limited to personal gossip and an intemperate e-mail Olbermann sent to a viewer in 2006 (in which he called MSNBC colleague Rita Cosby "dumber than a suitcase of rocks"; he later issued an apology and has since curtailed his communications with fans). But stay tuned: in February, he signed a new contract with the network. "Because of his personal demons, Keith has imploded everywhere he's worked," Fox News spokesperson Irena Briganti told the New York Times last summer, one of many salvos in the proxy war-of-words she conducts on behalf of O'Reilly. "It's obvious Keith is a train wreck waiting to happen."

Jim Savitt isn't so sure. Olbermann, he suspects, is right where he wants to be. "Keith has a magnet inside him that pulls him to controversy," he says. "I think he enjoys it. He likes to be where the action is. "Others say that, unlike Network's Howard Beale, Olbermann does not appear to be a man on the edge. He has a steady girlfriend, talks about having kids, and somehow even mended fences with ESPN, rejoining his old partner Dan Patrick in 2005 for an hour on ESPN Radio every weekday afternoon. "He has the courage of his convictions, and he seems comfortable with his role," says Peter Schacknow, who just attended a forty-eighth birthday party for his old 'VBR colleague. "I'm shocked at what he's become. This is a late development. He's found his voice."

Judging by the adamantine certainty in that voice, Olbermann seems unlikely to lose it again. This, of course, is what drives his detractors, liberal and conservative alike, to distraction--the whiff of the demagogic in his commentaries, the sense that he sometimes indulges in the same overconfidence that afflicts his opponents. Not so, Olbermann says: he is merely arguing the inarguable. "There's an old saw--‘It's just my opinion, but I'm right,'" he says. "I don't even view it necessarily as commentary. I prefer to think of it as analysis. Which is, of course, commentary that the commentator views as correct."

And then--briskly, because he's due on the radio in an hour--he's up and out the door. Like any good broadcaster, Olbermann doesn't end a conversation with the usual civilian pleasantries. He has a sign-off. "We're not liberal," he announces brightly, striding to the lobby. "We're right!"