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Exclusive Look Back: Conan O'Brien's Private Thoughts, Worries Ahead Of His First Season

Jul. 3 2021, Published 7:03 a.m. ET

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For almost three decades, late-night televisionʼs Conan OʼBrien, 58, spent his time tirelessly avoiding the lengthy shadow left by the immortal reigns of David Letterman and Jay Leno. The latter turning into an embarrassing and controversial network mess.

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But now that's all over, and the surprisingly still red-haired, freckle-faced, one-time comedy writer has walked away from it all.

Nobody aside from a handful of entertainment insiders had ever heard of a 6ʼ4”, skinny Harvard grad named Conan. That was until May 3, 1993 when Saturday Night Live creator Lorne Michaels shocked America with the news that OʼBrien would be taking over for the king of late night, David Letterman, who was heading over to CBS.

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exclusive interview conan obrien private thoughts worries first season ok
Source: MEGA
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Redefining the word pressure (at stake for NBC was a reported $70 million in advertising revenue), the unlikely Late Night successor from Brookline, Mass., set out on the seemingly impossible task of replacing a legend.

Meanwhile, yours truly was a rookie in the magazine business. I had just a handful of Hollywood stories under my belt and was desperate to make a name for myself. At the time, Michael's unlikely pick to replace Letterman was front-page news. So I took my shot: The dreaded interview request.

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Call me overly ambitious. Call me too dumb and inexperienced to know that I had no chance to land an exclusive one-on-one with the new talk of late night television. It's worth noting this was before everyone on Earth had a podcast or blog. (Not everyone with a cell phone was a "journalist.")

The next day I got a call from a young publicist (because email didn't exist yet), who I'm sure is retired by now. My interview request was approved! Little did I know at the time, I was sitting down with a future Late Night Hall of Famer.

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A week later I published my story and tossed the cassette tape of our chat in a dusty box. There it sat for the next 30 years... Until now.

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When I heard O'Brien was calling it a career, I thought back on my interview when we were both two ghostly pale ginger's starting out on our chosen careers. I listened to our chat, and how unsure O'Brien was about his future — how humble and respectful he was toward the legend he was replacing. Here are a few sound bites from that big score so many years ago.

OK!: Describe what itʼs like having your dream come true. 

Conan OʼBrien: (Laughs) Ummm..itʼs very nice! You always hear these things like thereʼs supposed to be some ironic twist to it. At first you think is this going to be like a Twilight Zone episode where you really wish for something like your own talk show, then you get it, and the audience are a bunch of zombies or something like that. Or you'll get your own talk show but the twist is, (Yelling) YOU'LL HAVE TO DO IT FOREVER! It's not like one of those things where I won a boat and I can just sit back and enjoy it Itʼs a lot of work. I think even if you do this for 20 years, you never get to the point where you can say, "I got this thing licked, and I donʼt have to worry about it anymore. I can just show up."

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Are you very critical of yourself after each show?

Yeah, but I try not to overdo it. I think it would be worse if I did just one of these shows a week. But I do five a week, so it's not really healthy or constructive to micro-analyze them. Do you know what I mean? You can't get obsessed. Instead, you kind of have to look for trends.

Give an example of what you mean by "trends."

For instance, I might see what I have a tendency to go too long with the second guest. Or I might see that I have a tendency to go too long with the first guest. That kind of thing.

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After only a couple of years you've gone from a virtual unknown to a high-profile celebrity. How do you think you've changed?

Oh man, I think I've become such a jerk. I really have.

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You say that in jest but the truth is prior to taking over for Letterman, you had the reputation of being a really nice guy. However, one would think with the responsibilities of your own show, you might be prone to lose it now and then.

If you isolate yourself you probably change. But I work with too many people who know me from before. Do you know what I mean? And Iʼm pretty close to my family. So I donʼt think I've changed. (Laughing) They've changed!

So in other words, thereʼs no whispering going on behind your back that youʼre aware?

Yeah, they're probably saying to each other, "He used to be so different. What happened to him?" I mean, of course, you canʼt always be a nice guy. If there is something that I think hurts my show, or if there is something that is happening with the show that I think is not constructive, I'll have to say something about it. Sometimes I just get irritated with people. I don't think it happens that often, and I think it's for the good of what we're all doing.

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It sounds like a far cry from your writing days with The Simpsons.

Well, I think now I'm probably more prone to getting angry because I'm out there every day, and it's my name at stake. Do you know what I mean? When you work for a show like The Simpsonʼ other people are calling the shots. But now I'm the one calling the shots. So there're going to be times when I say, "No, I don't want to do that." I don't do it in a mean way but it goes with the territory. But other than that, I don't think I've really gone through some major personality change.

Are you concerned when television affiliates around the country voiced their displeasure over your lack of David Letterman-type ratings?

Well, there is always going to be somebody who's not happy. I mean America's a big country, and you're always going to be doing well in some markets and not so well in others.

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Since your first show, your ratings have been climbing. That's gotta be a good feeling.

Oh yeah! The ratings are up, and the affiliates actually seem happy. I still have 100 percent affiliate clearance. I think most of them understand that these things take a little while. I always say that it's a two-fold adjustment. It's me getting comfortable in the job, and then at the same time, it's people getting comfortable with me being on TV at 12:30 at night. I think actually what makes it easier on the affiliates is if they see growth, especially in the Nielsen ratings. Of course, they will always be some markets where you won't do as well as you would like, but I think everybody has that problem. Even Dave (Letterman) had affiliates that were trying to do stuff to him. I think that kind of problem is going to be there 10 years from now.

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Is there a region of the country where you find that you struggle in the ratings the most?

Ummm...not really. Sometimes I''l have trouble in the real rural farm areas where they go to bed early. That's always tough because they don't watch a lot of late night TV.

How do you correct that?

I thought about shipping coffee into those areas—huge tanks of the stuff.

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It was reported that you signed a one million dollar a year deal with NBC with a option to renegotiate after one year. However, those close to you felt that you would have done the show for nothing. How much of an exaggeration is that?

Well, I never like to get into what I get paid because it's never quite accurate. It's never quite as much as people say it is. But...(pausing) let's just put it this way. I was never in this for the money. This was never a money-making proposition. It's too hard. You don't get into something like this to make money because itʼs too hard of a job. There are other ways. I would sooner go to Vegas with $500 and try and do it that way. If I just wanted to make money, I would have produced infomercials. Certainly, I don't want to go on the record saying that I would do it for nothing, but I love doing it enough that the money isn't a big factor.

When you hear the name Joe Franklin, what's the first thing that comes to mind?

(Laughing) Pizzazz! Pure energy! A showman the likes of which we'll never see again.

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While we're on the subject of former talk show hosts from hell, do you ever have nightmares where you wake up in the middle of the night, look in  the mirror and see Dick Cavett's face staring back at you?

(Laughing) Well, actually that has happened a few times. You see, Dick Cavett doesnʼt have a place to stay. So he's been staying with me. It's really not a nightmare.

Here's a question I bet you thought you'd never be asked. Whoʼs your favorite thus far?

I would say that for pure entertainment value and also meaning, that it had to be David Letterman. Him coming on my show meant a lot. Not only was he a good guest, but I think symbolically it meant a lot for him to come on. He seems to think that we're doing a good job, and I want to believe he's sincere when he says that.

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Iʼm sure he can relate to your situation.

Exactly. He knows what it takes to do something like this. For him to come and anoint the show meant a lot to us. I don't know what it meant to America, but it meant a lot to me personally. Also, my staff and I have a lot of respect for what he did with this time slot, and now we're trying to do something interesting as well.

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How did you feel when Howard Stern trashes you?

Well, that's sort of what he does. To be honest, I listen to his show, and I think Howard's funny. Think of it this way, why would he give me a break? What he does is go after people. I mean who doesn't he insult? Do you know what I mean? I'm the guy who replaced Letterman, and I'm kind of the underdog right now so it kind of makes sense to trash me. If Howard wasn't going after me on the air. I would think something was wrong. So as long as he's talking about me, I'm happy.

Like so many other brilliant comedy writers, youʼre a graduate of Harvard University. What is it about Harvard that produces so many great comedy minds?

I just don't know. I think it's a good training ground.  A lot of bright people there start writing comedy when they're 18 or 19 and make the mistakes that they would have made when they were in their mid-twenties. I think it's a good training ground so it kind of makes sense. Why it's grown so much, I don't know. I think it's just a trend.

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I read that the late Bob Crane from the '60s sitcom, Hoganʼs Heroes, was your childhood idol. Is that true?

Ummm..he was an influence. I don't know if he was my idol. What I thought was cool was that he had black hair and a black leather jacket. I always thought that was the way to be.

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Physically you have some very interesting features. Is it true that as a child you hated having red hair and freckles

Well, when you're a kid you get called a lot of names—carrot-top, match-head.

Is it true that you were so afraid of women in high school that you opted not to attend your senior prom?

Itʼs like an Irish-Catholic thing. I think every guy has a mysterious fascination with women. I mean what the hell are they?

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Are you still uncomfortable around women?

Oh no! Actually, they are my favorite guests. No, I would say that just because that was true when I was a sophomore in high school, doesn't mean that it's true now. I also had bad skin in high school and that went away.

If this late night gig doesn't work out, what will you do?

If this late night job doesn't work out Iʼll probably become a casino greeter in Atlantic City.

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