A look back at David Letterman’s legendary late-night career

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(CBS) – In his final days in the Ed Sullivan Theater, David Letterman is reminiscing.

“There was a big, gray, plastic trash garbage can here. And I was up in the balcony and I had a football with me. And I said, ‘I– let me see if I can drop the football into the trash can from up there.’ One shot, bang, zoom. And I thought, ‘Oh, this is– this is a sign of something.’ So I– do we have the thing here? Let’s try it again. Do you mind, Jane?”

We were game.

“Well, we can do anything you want. We have to go up here. Somebody stay down here. Somebody get the can, I’ll be upstairs,” Letterman said.

We were of and running, along the catwalk and into the balcony. It took him 10 tries.

“I’m just happy I was able to do it.”

“Yeah, and you were. That means you can’t leave.”

“Okay, no, no, we have to leave,” Letterman said.

And leaving he is, with an astonishing lineup of guests in his final weeks on the air.

“This is really a nervous place to sit, the one you’re sitting in. Next to Dave when you’re on his show, I– I have been honored to be among the 18,000 guests, do you remember?,” I asked him.

“Yeah, yeah, many, many times when we both worked at NBC, for sure,” he said.

“No, seriously. Do you remember stuff? Do you remember people?” I pressed.

“I– you know … I don’t remember things we’ve done on the show. People are always saying, and — and here lately we’ve bee showing video of — of things we’ve done on the show. I have no memory of it. No memory of it. And I don’t know if you had this trouble with The Today Show, but driving home at night or when I get home, Regina will say, ‘Well, who was on the show?’ And then it’s like, ‘Yeah, who was? I don’t know, was it — it mighta been Reese Witherspoon. But then again, it mighta been Regis Philbin. I don’t — I’m just not sure.”

I started appearing on Letterman’s show in the early days. Once, he thought it would be fun to make our voices sound like we’d inhaled helium. I wasn’t so sure.

“I want to apologize about the helium thing,” I began.

“What? See, I don’t remember. You – you were on helium?”

“No, you had some — some little thing where — where if we spoke, you spoke or– our voices sounded like…”

“That we were on helium, yeah, yeah, yeah.”

“And I wouldn’t say a word. And I must have taken a note — note, paper, something from your desk. And I — I wrote notes. But I just– you did whatever you could to make me …”

“Right. But see, you — you behaved the way humans are expected to behave. My behavior was aberrant. So I owe you an apology.”

There’s often something faintly apologetic about David Letterman, which goes back, as we do, having both grown up in Indianapolis. I recalled an appearance we made together in the 1970s.

‘You told the high school kids about your feelings about your success. You said, ‘It’s like robbing 7-11s. The money’s good, but you know you’re gonna get caught.'”

“I hope I said that. In those days I was — probably not you — waiting to be tapped on the shoulder, ‘Okay, the real guy’s here. You can go home now.’ That’s — that’s what I was always motivated by, that fear — the fear of failure. And then I have to, ‘Oh darn.’ And then, you know, I wasn’t chosen again so I go back home. That was always the concern.”

In high school, Letterman was not a candidate for most likely to succeed. But that’s where he found his calling.

“I knew exactly what I wanted to be. My sophomore year in high school they offered a speech class — public speaking class. So I signed right up. All right, first day of class, everybody has to stand up and give an impromptu speech about themselves. And I got up when it was my turn and I gave the speech — it had to be, like, two minutes or something. And I sat down and I said, ‘Wow that was easy,’ to myself. And I had never said that about any other class in my academic career prior or after. The fact that I could put something together that seemed to fill the requirement was — I couldn’t do it in any other class. I couldn’t do it in algebra, I couldn’t do it in English, I couldn’t do it in history. I couldn’t do it anymore. Metal shop, maybe.”

After college at Ball State, Letterman became a local jack-of-all-TV-trades.

“I started when I was 20 years old in 1968 or something in Indianapolis,” he recalled.

“Yeah, I remember you. … the weather and the weekend movies. You were … hysterical,” I said.

“No, no, maybe not.”

One of the most important decisions he ever made was to get serious about comedy and move to Los Angeles. Within a few years, he had landed an appearance on “The Tonight Show” with Johnny Carson that would change his life.

“And it’s white hot adrenaline. That’s all it is. Then you go and you sit down and you talk to Johnny. And it’s like you’re sitting on the knee of the Lincoln Memorial and Lincoln is talking to you. You know, it’s like, ‘Holy God, it’s the guy on the $5 bill is talking to me.'”

More appearances on “The Tonight Show” led to a morning show.

“At 11:00 a.m. — ’cause it was bizarrely a daytime version of what you do now — my office would be filled with people watching, you know, your — your show. It was — it was brilliant,” I recounted.

“It wasn’t brilliant, Jane. It was– but it was– it was like standing on an overpass looking at a chain reaction collision, you know, that goes okay, nine cars, 10 cars. ‘Oh look, it’s 100 cars.’ It couldn’t have been more poisonous. They had to get away from it.”

The show lasted just four months.

“I really thought that’s it. You get one shot and away you go,” Letterman said.

Though Letterman was a ratings disaster in daytime, NBC gave him a shot at late-night.

“I started out, for God’s sakes, at 12:30 following Johnny Carson. So that was a pretty safe place for a kid who didn’t know what he was doing.”

And that’s what the — the network said, ‘Find some kid who doesn’t know what he’s doing, the only one in America, or that would be — here he is from Indianapolis, Dave Letterman.’ No,” I joked.

“That’s, no that’s exactly how that …”

“And they continued to give you paychecks … to do this … for them.”

“Yes. But it — it was all different. I couldn’t get a show now.”

For years, Letterman was the heir-apparent to his idol, Johnny Carson. But when Carson retired in 1992, the chair went to Jay Leno instead. Letterman, deeply and publicly wounded, moved to CBS.

“I’ve never considered myself to be a bitter person. When Johnny Carson retired and I was not given the job as host of the tonight show, I was disappointed, but – my way of thinking, it was not bitter,” Letterman said during a press conference.

He turned “The Late Show” into a comedic laboratory.

There were top 10 lists and stupid pet tricks.

Television’s most reliably irreverent personality is feeling kind of nostalgic these days.

“Now I am told by some staff that you’re seen in, not odd but unique places around the Ed Sullivan Theater, as if you’re kind of trying to soak it all in,” I put forth.

“Well, that’s absolutely correct. So when I’m down here during band numbers or during commercial breaks, I will go to various places and — and try to memorize what it looks like and how I feel, and look at the audience and — and get the scale of things because even though I’ve done it for so long, I — I don’t ever wanna be without a fairly accurate, fairly vivid impression of this experience.”

By any measure, David Letterman took his craft to new heights. His comic genius recognized by everyone … except himself.

“I had this conversation as recently as last evening with my wife. And she will go to this strategy to pep me up. … She says, ‘Everything’s fine and you’ve — you’ve accomplished some things and you should be proud of that.’ And — and I don’t believe her. And so we, you know, we have to be separated. We go — we go to neutral corners.”

“Life can be hard work for you,” I said.

“Well, for anybody for God’s sakes. Isn’t it really?”

Letterman’s time in the late night spotlight has had its share of good times and bad times — some of his own creation.

“You’ve talked about alcoholism. … Is that for real,” I asked. “I mean, you’re not just talking about ‘I drink a lot [or] drank a lot.’ But you were or are an alcoholic?”

“I guess you — you’re always an alcoholic, yeah.”

Letterman said he started drinking when he was about 11 years old.

“It was that old thing where my dad used to like scotch and soda.And, ‘Here, here, Dave, you wanna try one?’ And I tried one. And I just thought, ‘This is fantastic.’ … It was delightful. I — I just — I loved everything about it.”

“But then in high school it– it was part of the culture. And in college, it was mandatory. And then when– when you get outta college people start to taper off. And I was surprised. I would look around and [ask] ‘Where are all my drunk buddies?’ And you had to go looking for a drunk buddy here and there. They weren’t prevalent the way they were in school. And I drank right through ’til I was 34. And I had the — the show at NBC and I just said to myself, ‘You’re- – you’re a fool, you’re a dumb fool. You can’t do this. You — you know, they just don’t give these shows to everybody. You have one. And– and you drink yourself into trouble, you’re done, pal.” And I just quit. Never, never took another drink.”

“It was huge — because I’d be dead. I — I’d just be dead.”

Remarkable candor for a man so famously private, though Letterman’s personal life HAS sometimes become conspicuously public.

In 2009, he admitted to having liaisons with staffers, after a CBS News producer tried to extort money from him.

Letterman delivered an on-air apology. The revelation came just months after his marriage to long-time girlfriend Regina Lasko.

Letterman is no stranger to headlines, as when he underwent quintuple bypass surgery in 2000.

“I don’t know anybody who has had open heart surgery loved it.”

“It was great because it was all about me. Oh my God it was great,” Letterman said. “And people would come in and — and they would worry about me and they would help me outta bed and they would walk me around the wing of the hospital. And then after I got out of the hospital they would come up to the house and — it was delightful.”

He celebrated his doctors on the air and admits his surgery did have a surprising emotional impact.

“I did get weepy, which I — I don’t think was depression. … It was a joyful weepiness. You know, I would hear a certain song or a certain image or, you know, be talking to my wife and I would just explode into tears. But it was never that — that, like, clinical depression where it’s, like, I can’t get out of bed. ‘Oh my God, I can’t get out of bed.’ It was not that.

“Have you ever had that?” I asked.

“Yes. Yeah, I’ve had that. And that’s just — that’s the worst. That’s really the worst. It’s — it’s a bottomless pit that sucks you and keeps you suckin’ you down. And I — I never — I’m glad I went through it because now I understand it.”

“One episode or more episodes?”

“One. One … it lasted about six months,” he said.

It was triggered, he said, when he went off prescription medication after a painful outbreak of shingles — which forced him off the air for more than a month.

Just recently, Letterman found himself a bit player in Brian Williams’ woes. The NBC news anchor was caught embellishing the truth in a story he told on Letterman’s show about a helicopter mission in Iraq.

Typically, Letterman’s version begins with a joke.

“I went to his dressing room and I said, ‘You know, that helicopter story, it would be so much better if you mentioned you were in the — chopper that took the hit,” he said, laughing.

Williams had been a frequent guest on late-night talk shows and reportedly even lobbied to host one.

“He would’ve been fantastic. He would’ve been great. He’s … a natural born broadcaster.”

“You can see the future as well as I can only maybe a little better ’cause you’re taller. Do you think he’ll end up in comedy?” I asked.

“No. No, I don’t think so. I think this will sort itself out. I don’t know how, but I think it will — in a year or two it will be a dim memory.”

Letterman, meanwhile, is looking forward to spending more time with his family.

As his audience knows well, his heart belongs to 11-year-old Harry, born when Letterman was 56.

But first he has to say goodbye.

“You had me on during an important point in my life, when I was leaving ‘The Today Show,’ which was ’89-ish. It was probably the most vivid year of my life, and I was a guest on your show. And now you’re having what I’m guessing is a profoundly vivid moment in your life. And I’m grateful that you’re sharing with it us.”

“Well, thank you very much. And I … I’m naked and afraid because — and I, it’s so cliché, but I’ll share it with you anyway — any enormous uprooting change in my life has petrified me. Really petrified me. But once I’ve come through the other side, the — the reward has been unimaginable.”

On Wednesday, David Letterman will walk out the stage door for the last time. And it’s not clear this time what’s on the “other side.”

“I notice how when you talk about it you say that you are retiring from the show. … Retiring form the show is not the same thing as ‘I’m retiring.”

Right. Yeah, I — I think I’m trying to make it more palatable to myself. But I — I doubt that anybody will ever see me again,” he said before breaking into a grin and laugh. “Yeah.”

I doubt that.

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