Keith Olbermann Keith Olbermann

Bill O'Reilly and Keith Olbermann are engaged in one of the most visible rivalries of the decade — a conflict that may be rooted more in their similarities than differences. Both talk show hosts are former straight news reporters who share not only a formula for talk-show success, but a mutual respect for Tom Snyder, whose 1970s talk show Tomorrow set the bar for thoughtful, entertaining talk. Olbermann and O'Reilly make our Players list for best epitomizing the transformation of news in the 2000s. While CNN ruled the '90s with an emphasis on breaking, opinion-free reports, The O'Reilly Factor helped Fox News become the cable news leader with a show that mixes reporting, reflection, and rampant editorializing. It's the same formula adopted by Olbermann's Countdown, which has led MSNBC's increased emphasis on opinion. Critics paint O'Reilly and Olbermann as blustery, cartoonish bloviators of the right and left, respectively, and take them to task for not playing it straight. But both men — among the influential television industry players interviewed for's Best of the Decade section — would just say they speak the truth. Click here for our interview with O'Reilly or read on for our talk with Olbermann.

Read more of our conversations with the most influential people in TV Can you walk us through the evolution of your shows?

Keith Olbermann: It's like one of those medieval morality plays, because the decade started with Fox firing me from baseball and cable sports coverage because I broke a story about [News Corp. owner] Rupert Murdoch talking about selling the L.A. Dodgers. How are things different now from the start of the decade?
My contention even in 2000 was that fewer and fewer people were watching the newscasts without knowing the news already, or having some idea ... and television news was going to change. And if it wasn't going to change into something more analytical, it was going to change into something that was purely beat-people-over-the-head partisanship. And I was trying to figure out ways to do something novel and original that sort of competed as a television show — that was honest and kept journalistically sound, but was truly competitive with the latest Law & Order episode. It had to move that fast. And I was trying to figure out how to do that, and then circumstances kind of directed it that way. So for me, personally, the environment changed; and obviously the industry totally changed, and the country largely changed. ... 2000 bears no resemblance to 2009 in any of those areas. And I also had mostly dark hair in 2000. What do you anticipate about the end of the next decade?
Olbermann: I think you're going to see more and more of attempts to do what we're doing. In many ways, they will be complete misses. ... News is going to become increasingly analytical. And I don't know what the place is for the broadcast-network newscasts.

Gallery: See who else made our Players list What are you most proud of?
Olbermann: What I'm most proud of, I suppose, is that when it came time to do the first of these commentaries — with a White House in power that really didn't brook any kind of criticism, and a very tepid opposition ... my attitude was, if I'm going down because of what I'm going to say ... I didn't waver. One of the things that maintains the status quo in television or anything else is a big paycheck. Because you can get really enamored of it, you can get protective of it. What are you least proud of?
Olbermann: Least ... That most of my disagreements and most of the reputation I have for being disagreeable with employers was predicated on really worthwhile debate that they would engage me with. And I didn't realize to the degree that they were being generous in doing that, and respectful in doing that. And when I didn't get my way, I normally would just go public with it. Which was just ridiculous. I really don't understand why more people didn't hit me in the head with a brick. Do you have any advice for others in the business?
Olbermann: If you're not introducing something of yourself and your own beliefs to what you're doing on the air, they can replace you with, now, a decreasingly expensive computer that can just read the news for you. ... If you are being yourself, some people will dislike you, some people will like you. You have to run that risk. Fortunately the industry has gotten so niched.

Watch videos of Keith Olbermann Inspirations?
Olbermann: I don't claim any connection to the works of [legendary CBS newsman Edward R.] Murrow or any of the real greats ... other than as a fan. But when I was 13, CBS reran a lot of the Murrow stuff, including the McCarthy broadcasts and a lot of CBS Reports, as a summer fill-in show on a Saturday night. I was probably the only 13-year-old kid asking his parents for permission to stay up to make sure they could watch a newscast on a Saturday night in 1972. ... Two of my other heroes, [the long-ago comedy team of] Bob Elliot and Ray Goulding ... [1960s star Yankees pitcher] Jim Bouton, who wrote the book Ball Four ... [and] a local sportscaster. He actually taught me where the line was [for taste and how far to go with jokes]. ... Tom Snyder was a great influence on me. It is hard to believe — this may tell the entire story of the television news industry in 35 years — that he was not considered eligible for consideration to be the anchorman of the NBC Nightly News because he'd also done the Tomorrow show, and therefore was also a talk show host. How can you be a network news anchor and a talk show host? No, no, you can't do that. What do you watch now?
Olbermann: [The Soup] is just brilliant. I like pretty much everything Seth McFarlane puts out. The Simpsons. [David Letterman's Late Show last year and this year] has been fabulously relevant and politically decisive in many respects. ... [Prime Minister's question hour on C-SPAN] is one of the great entertaining shows that just happens to be about politics ... I'm a devotee of the MLB Network. Which I think is an exceptional product. I don't recall a startup doing a better job in terms of what the product looks like. Anything you wish you were involved in?
Olbermann: Three sitcoms: The Larry Sanders Show. There was once a character named K.O. — my initials — who Rip Torn yells at off-stage. We never see him. And the whole line was: "K.O. Ice! Ice for Larry's balls." He's riding a horse or something like that. Well, all of the Larry Sanders fans at ESPN the next day were shouting at me all day: "K.O. Ice! Ice!" [Arrested Development] is almost Catch-22-like in its intricacy ... The Fall and Rise of Reginald Perrin [which starred Leonard Rossiter, and essentially was about midlife crisis]. I loved it when I was 20, and I love it when I'm 50.