20 Questions: Keith Olbermann
April, 1998
After five and a half years co-hosting ESPN's ''Sportscenter,'' affectionately dubbed ''The Big Show,'' Keith Olbermann has a gig of his own: ''The Big Show With Keith Olbermann'' on MSNBC.
Olbermann is happy. For now. His departure from ESPN last year was not entirely amicable. He and co-host Dan Patrick had arguably built ''Sportscenter,'' a roundup of the day's jock news, into the network's signature show. Their twist on that staple of the sports broadcast--highlights--included banter, ad-libs and such a large volume of catchphrases that the pair included a glossary in their book, ''The Big Show: Inside ESPN's Sportscenter.''
But Olbermann chafed at what he terms ESPN's ''rules mentality'' and admits, ''I stopped being a sports fan.'' He claims that his enthusiasm was dampened by team owners' machinations in shifting franchises and the pervasive hype surrounding professional sports. ''It was Upton Sinclair in the stockyards,'' he recalls. ''I saw the corruption.'' He left the air before his ESPN contract expired.
Contributing Editor Warren Kalbacker met with Olbermann in New York. Kalbacker reports: ''Olbermann wanted to set the record straight regarding the brouhaha over his description of Bristol, Connecticut as the most godforsaken place in the East. 'I was never asked the follow-up question, which is ''Why?''' he told me. The answer he would have given: 'That's where ESPN is.' Olbermann insists there's nothing wrong with Bristol and its environs. 'Fine places. If I had been married with children, the area would have been a great place to live.' Even Mike Tyson's residence in neighboring Farmington presented no problem for Olbermann. 'Mike Tyson is legally a cousin of mine. He was adopted by Cus D'Amato, who was his trainer, and Cus' niece is my aunt by marriage--she's my father's brother's wife.'''
1.
Playboy: You appropriated the nickname of your former show as the formal name of your current show. We understand you had to resolve a dispute with your former employer about using the title The Big Show.
Olbermann: ESPN was just being pissy. It was suggested that there might be an intellectual property problem until I pointed out that I had appropriated the nickname of my previous show for use on its network and that I'd called my show in Los Angeles The Big Show. I used to call my radio show at Cornell University The Big Show. There are so many Big Shows that during the controversy over the title I did an interview on a radio show called The Big Show. Nobody has a claim. If anybody has a claim, maybe it's Ed Sullivan. If I go somewhere else after this and try to call a show The Big Show With Keith Olbermann, NBC would have a case against me. I can use The Big Show again and I can use Keith Olbermann again, but I can't use them in that combination. Keith Olbermann's Big Show I probably could get away with.
2.
Playboy: You introduced the premiere Big Show with what could only be described as a mission statement. Why?
Olbermann: Phil Griffin, the executive producer, and I had many meetings last summer about what we wanted to do and what the tone of the show was supposed to be. I kept hitting him with ''skeptical, not cynical.'' Let's not act like everything is untrue, but let's question whether or not it is. Let's take that as our attitude. If anything, it was inspired by Citizen Kane, when Kane bought the newspaper and made his statement of principles. If a guy comes on who is completely identified with sports, and suddenly he's doing what is more or less a news broadcast, he should explain what the hell he's doing there and not say, ''I'm lost. I thought this was a place to get a Starbucks.''
3.
Playboy: A recent guest complained on the air about not being able to pass through NBC security in Los Angeles to appear on your show. Do you think The Big Show's ratings might grow to the point that NBC's West Coast operation is aware of its existence?
Olbermann: That happens all the time. They didn't know what MSNBC was, and they sure as hell didn't know who I was. As a kid, I remember hearing stories about Tom Snyder not being able to get into NBC when he anchored the local news and hosted the Tomorrow show. If the people who do the stopping were really good at their job, they wouldn't be doing that kind of work anyway. We would have already sucked them into management. There aren't that many qualified television people around. If we have a good one down there at the front gate, we're probably not using him as well as we could. There were no security guards at ESPN. I once had a receptionist escort an overenthusiastic fan--I wouldn't want to call her a stalker--to my desk. This was like a guided tour--''Keith is working only this one Saturday, so why don't you fly in on that day?''
4.
Playboy: Does working for General Electric's NBC beat working for Disney's ESPN? Do you get hefty discounts on major appliances?
Olbermann: Hands down. [NBC news correspondent] Brian Williams came to the dinner where they were trying to sell me on going to work for the company. They didn't know they had already sold me--I'd left that out to make sure I'd get the free meal. Williams snuck up behind me and whispered, ''Lightbulbs. I can get you all the lightbulbs you can eat, aircraft components, refrigeration equipment, anything you want. Anything but money.'' So they tried to use that as a hitch. But honestly, at NBC the idea is: What can we do to relieve you of these workaday burdens so you can focus on doing your show? At the last World Series, in Cleveland, everybody had mis-guessed the weather. It felt like 20 degrees. I'm thinking maybe I'll go out to get some underwear. A production manager, without being summoned, asked, ''Are you warm enough? What do you need?'' And I'm thinking maybe underwear. She told me they had people to do that for me. They'd get me thermals. The coats were coming in. There would be turtlenecks. Did I need moon boots?
5.
Playboy: Williams, whose MSNBC show follows yours, has been mentioned as a successor to Tom Brokaw. You and Williams appear to have a thing going. Are you looking to hitch on to his coattails?
Olbermann: How do you mean that? We have a little bit of fun on the air. There is some belief that Brokaw would never give up his job under any circumstances. He has stamina: ''Tom Brokaw turned 106 today, and it was covered by NBC's George Lewis.'' My professional aspirations long ago ceased to be specifically defined. My dream when I was a kid was to do the major sporting events and then have a nightly news show. Well, I have that now. Brian is brilliant at what he does and, apparently, it can be applied for an hour at a time every night in what is to him a very satisfying method. The irony of the Brian Williams story is--and I use this term measuredly--that he's crazier than I am. He is intrinsically funnier, stranger, makes more bizarre cultural references. He's an instantaneous mimic and very quick with an insult or sardonic remark. I sat there at that dinner, while he was throwing these things back and forth, and I was watching NBC news executives seated across from us wondering how they could turn this into a show.
6.
Playboy: An ESPN producer once confessed to us he'd fallen asleep in the production truck during a major event. Is the entertainment value of sports vastly overrated?
Olbermann: It is overrated. I truly believe that if you could not buy beer in every sports stadium and if there were no gambling at all, the total attendance at all major sporting events in the country would be under 700,000. It's not that there isn't great drama in sports, but nowadays there is so much sports that nothing stands out. The Super Bowl is a brand name. The World Series is played so late in the year that the pitchers--they will not admit this for the record--are so weary they can barely see the plate, let alone throw that critical fastball over the corner. They're playing in 15-degree wind chills. They can't feel the ball. The whole process used to be 50 percent hype, and you could find the wonderful stories behind it. You could find the obscure jockeys who were really worth your time, or you could be a fan of a utility infielder who'd be there for five or six years. Now it's 90 percent hype. And merchandise. It's so discouraging, because when you are at the center of it, you become part of a process that I've described as the sports media complex. Even what seems dramatic is so immediately overtaken by money. Tiger Woods was instant hype, and I was instantly tired of it.
7.
Playboy: After years of broadcasting from behind a desk, what's it like to work in dress pants on an open set?
Olbermann: Being in a full suit is a new experience. I've found that girls really go for it. Five and a half years in jeans and a shirt, tie and jacket--no shoes on really hot days--and I never got up from behind the desk. Now I walk around in a suit and I get stared at. It's a nice feeling. Dress up, boys. I may have hit the first wave of this, but girls like suits. I haven't gotten too many comments on my shoes--usually loafers--though some women seem to be interested.
8.
Playboy: ESPN once suspended you for two weeks for ''actions against company policy''--such as promoting your book without permission. Do you consider yourself an example to all of us who struggle with authority?
Olbermann: I served my time, and I've only recently been able to admit this: For five and a half years I wondered if it was me or if it was them. Was I a pain in the ass? Is my hatred of authority that great? Now I can say with absolute conviction: It was them. There was such a corporate ''all we have are the rules'' mentality at ESPN that I feel like I've been released from prison. There is a lesson to employers: You can behave humanely, and it needs to start at the top. The lesson to employees is that you can go work somewhere else, and your value as an individual can still be redeemed.
9.
Playboy: You're a cigar connoisseur and a baseball aficionado. Now that you're in the news business, are you preparing questions for an interview with Fidel Castro?
Olbermann: Yes. I would certainly open with cigars and baseball, and really straighten out if he got a serious scouting look from the Washington Senators--as did nearly every other Cuban in the Fifties. At one time the Senators had something like 300 Cubans in their farm system: man, woman, child, animal, plant. They figured out that it was a cheap way of scouting: Send a scout to a very small island where a lot of baseball is played. I'd see if I could get some cigars, though I prefer milder Dominicans. What I want to know is how it feels to be ideologically and physically isolated, now that all the countries that propped him up all those years don't exist anymore. He's aligned with North Korea, and I imagine Castro would think the North Koreans are kind of crazy and irresponsible. So why not back Cuba off from communism and go to humane socialism? Castro's exports would financially revitalize his country in about an hour and a half: baseball players-- third basemen, especially--and cigars. He could export the cigars directly-- open Fidel's Cigar Factory stores across this country and take advantage of the current cigar craze--and finance his own form of sophisticated socialism. Bring us that third baseman, Linares, and bring us Cohibas. Castro could be the most popular man in this hemisphere. He could be the commissioner of baseball.
10.
Playboy: The other night you made a reference to a mythical Greek highwayman with the expression Procrustean bed. Do you use your Ivy League education every day?
Olbermann: My Ivy League education taught me how to cut corners, skim books and take an idea and write 15 pages on it, and also how to work all day at the Cornell radio station and never actually go to class. I use my Hackley [a private school in Tarrytown, New York] education every day. We read about Procrustes in Ms. Gibbon's English class. Procrustes had beds, each a different length. He would never change the one he assigned you. Once you were in that bed, you had to fit. If you were too short, he stretched you. If you were too long, he cut off your legs. The symbolism was appropriate to what we were talking about on that show--making the situation fit your preconception--though I can't remember what the situation was. I've never gotten a complaint from somebody who didn't get a reference, no matter how obscure it was.
11.
Playboy: Your position against public financing of sports stadiums is well known. We assume you haven't been invited to visit any luxury boxes lately.
Olbermann: No. I'm not a popular figure among team owners. Bud Selig came to ESPN once for meetings and a lecture, but I wasn't due in the office till later. In fact, I wouldn't go across the street to see Bud Selig even if the traffic light were with me. Selig left a note on my desk that said, ''Dear Keith: Sorry I didn't get a chance to defend my positions. Sincerely, Bud Selig.'' This man, who held what was in my mind as a child the most powerful position in the free world, commissioner of baseball, somehow felt he had to justify his actions to me. I felt power and glory in this. Baseball owners called ESPN and tried to get me fired. Jackie Autry, Gene's second wife, who runs the Angels in Gene's dotage, tried to get me fired when I worked for a station in Los Angeles. Later, she tried to get me fired at ESPN because of something I wrote about her in a magazine. I wrote about her standing with a cigarette dangling mannishly from her lips. She didn't like that. She is a rather large, imposing woman.
12.
Playboy: You don't drive. Do you identify with Clint Eastwood's character in In the Line of Fire, who is a steely advocate of mass transit?
Olbermann: I'm a fan of trolleys and elevated trains. I can't drive. I hit my head, and I have a depth-perception problem when I'm in motion. Here in the city there are no circumstances under which you must have a car, so I don't worry about it. Public transportation has always been my favorite. When I was a kid, I used to go to the garage and look at the buses. I take the Third Avenue el in my mind all the time. Mom took me to the doctor for shots when I was four or five, and my prize for being a brave boy was a ride on the el. We lived on Grand Avenue in the Bronx. Much of my infancy was spent at the windowsill, watching the Jerome Avenue el trains go by--a perfect way to keep a thoughtful baby quiet. Chicago is fun, the els are great there. The Montreal system is wonderful. You get a payoff on the number four to Yankee Stadium--the sweep up out of the tunnel at 158th Street is a wonderful way to see the ballpark. And if you're coming in the other direction, you see the park appear a few stations down the line. Very effective. But the number seven out to Shea is still pretty good. I took it out to Jackie Robinson Night in the spring of 1997.
13.
Playboy: Can any American boy or girl grow up to be a television anchor?
Olbermann: Apparently any boy or girl has. This is the first job I've had with a broadcasting company that existed when I was in high school. ESPN was founded when I was starting my career. In 1980 I interviewed at CNN, and I was glad it didn't go well because I knew those poor fools weren't going to get on the air. It doesn't seem to be anywhere near the end in terms of the number of organizations. The analogy to sports expansion is this: When I came back to this town after years on the West Coast, there were people broadcasting sports on radio who would not have been qualified to listen to sports on radio. There has to be a shakeout at some point. I always give the same advice to broadcasting students: Learn about some other subject. If I could, I would go back and major in history. The one thing most young people seem to bring to broadcasting these days is that they really don't know anything but broadcasting. They should have some general knowledge. You never know when you're going to suddenly be switched from sports to news, and you are going to have to know where Iraq is. There are lots of people on the news right now who have no idea where Iraq is.
14.
Playboy: Explain the special appeal of Helen Hunt.
Olbermann: She was last month's ideal American woman. Last night I said Kris-ten Johnston is the ideal American woman. I'm fickle. Helen Hunt just seems like somebody with whom you could have an intellectual discussion or an alcoholic beverage, go to a movie, maybe go dancing and sleep with. What you want is a well-rounded individual. For me at 6'3 1/2'', Kristen Johnston would probably be more appropriate than Helen Hunt, a better eye-to-eye fit. I once went out with a woman taller than I, and I got to use a Ring Lardner line. He was 6'4'' back in the Twenties when everybody else was 5'4'', and he met a woman who was 6'5'', and he said, ''My goodness, this is the first time I've realized that women also have nostrils.'' I said that to her, but she didn't think it was quite as funny as I did. She was a basketball player and remains a friend to this day. Someday we'll all be working for her because she's sharper than anyone else I have ever known.
15.
Playboy: Do you store your baseball cards in shoe boxes or cigar boxes?
Olbermann: In album pages. I have a few in plastic holders. My feeling is, if you can't show the card to somebody in an album, there's no value to it. I have been an ardent collector, and as recently as two or three years ago I would still get the new cards when they came out. But the strike took a lot out of me, and card collecting was one of the things that didn't matter anymore. Plus the cards all look the same. They're too much. A baseball card is a posed picture. A kid looks at it and gets an inaccurate but more useful view of what an adult athlete looks like than he does by seeing a freeze-frame from game coverage. I want to see a guy with his cap off-kilter in a fake pose--winding up with just his hands over his head and standing next to the dugout at Yankee Stadium. Why he would be doing this, we don't know. The old cards are always fascinating and I still spend phenomenal sums of money to get something from 1887 or whenever.
16.
Playboy: OK, what card would you give us in return for our--?
Olbermann: I have two unissued 1977 Topps Reggie Jackson Orioles cards. I would trade one for an unissued 1967 Topps Tommie Reynolds card. The issued card says Tom, and the unissued card says Tommy. I've always wondered why the card says Tom Reynolds rather than Tommie Reynolds, which it says on the back. There was a question of how he spelled it. They had printed it originally as Tommy, he spelled it Tommie, and at the last minute a proofreader said, ''That's wrong, take it off. Call him Tom.'' About eight years ago, the proof card went out in an auction as one of a sheet of cards. I didn't bid on it. Call me. I will make a deal. The values aren't the same, but I'll swap one of the Reggies in exchange for that Reynolds and maybe something extra, something cute, something neat--or a little cash.
17.
Playboy: You're a historian of baseball. Care to wax nostalgic about baseball in the days before the designated hitter and electronic scoreboard?
Olbermann: To the average fan today, a game from the 19th century would be far more interesting than a game from the 20th century. Baseball was simpler and still experimental. It was faster. There was less specialization. There were pitchers batting fourth, and they were good hitters. A pitcher would go out and play right field on his off day, and the right fielder would come in and pitch. There were unfortunate rules changes: seven balls for a base on balls, or four strikes to strike out. You wouldn't have seen a great deal of home runs. Home runs are the prostitutes of baseball. Every couple of years, the owners say, ''We need more home runs. That'll draw fans!'' They've upped the number of home runs since 1910, when they introduced the rabbit ball. Part of the fascination with the embryonic game is that it was played a long time ago. There's nothing so beautifully stated as when James Earl Jones says in Field of Dreams, ''The one constant through all the years has been baseball. America has been knocked down, erased like a blackboard, rebuilt and erased again.'' That's absolutely true. When I was nine years old I watched Mickey Mantle struggle through the last couple years of his career. In his second year in the majors, he faced a relief pitcher for the Boston Red Sox named Al Benton. In his rookie year Benton had pitched to Babe Ruth. There's a living history there that we have in so few areas of life. Somebody taken from our time and thrown into the New York of 1935 would be overwhelmed by the lack of air-conditioning. But a baseball fan taken out of Yankee Stadium this spring and thrown into Yankee Stadium in the spring of 1935 would be delighted by the lower prices.
18.
Playboy: Do student broadcasters and equipment managers know something that those of us who once wore jockstraps don't?
Olbermann: Every American boy--and now it's every American girl as well--understands at some point that he won't be a pro athlete. Those who understand that at the age of 42 are ex-athletes or frustrated bankers who must play in family hockey leagues or fantasy leagues. Those of us who realized it when we were eight have become announcers or equipment managers. We're not more mature, just more realistic. I have a friend named Joe Magrane who as a rookie pitched the opening and closing games of the 1987 World Series for the Cardinals. Joe is now 33, and after recovering from arm problems he pitched for the White Sox in 1996. In that off-season he asked me about getting work as an announcer, but he decided to give it up. Leaving baseball was a trauma for him and it harked back to my realization. When I was eight, I knew intuitively that I could put 24 years into this, and at 32, I'd be no closer to being a ballplayer. I would argue that most people are better prepared to contend with it at the age of eight than they are at 32. I'm sure my crisis of realization was far easier to deal with than Joe's was.
19.
Playboy: Is the smirk your trademark facial expression?
Olbermann: If you were to ask me to smirk now, I couldn't do it. I will occasionally do the intentional raised eyebrow. Everything else so far has been a legitimate reaction. It's seen as a smirk, but it may be that I don't have sufficient muscular control of my upper lip. It must be a reaction to the lights.
20.
Playboy: The Big Show, and every other broadcast, calls upon panels of experts for comment on any subject. Is America in danger of becoming overpundited?
Olbermann: I saw this coming when I was a kid. At the Cornell radio station we used to be issued a book every year--the Cornell directory of experts. If a zebra burst into flames, there was a guy on the faculty or staff who could tell you how many times it had happened, what the likely causes were and what it smelled like when it first happened in the 14th century. That has evolved into ''I saw him on Court TV, let's grab him.'' People have been on my show live, and appeared on tape on CNN and on Fox News. They're punditing on all three channels on the same day. We'll eventually have an expert who will talk about how much we've overdone the expert thing. He will be the expert who will rank actual expertise as opposed to punditry or punditude. Punditing will be a gerund. We'll go one step beyond and everybody will realize how absurd it is. The novelty of six lawyers appearing after every case and yelling at one another will eventually go away. How many trials of the century can you have?
Like what you see? Upgrade your access to finish reading.
- Access all member-only articles from the Playboy archive
- Join member-only Playmate meetups and events
- Priority status across Playboy’s digital ecosystem
- $25 credit to spend in the Playboy Club
- Unlock BTS content from Playboy photoshoots
- 15% discount on Playboy merch and apparel