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CNN LIVE EVENT/SPECIAL
David Letterman Says Goodnight. Aired 7-8p ET
Aired May 23, 2015 - 19:00 ET
THIS IS A RUSH TRANSCRIPT. THIS COPY MAY NOT BE IN ITS FINAL FORM AND MAY BE UPDATED.
DAVID LETTERMAN, TELEVISION HOST: I happen to be the most powerful man in American broadcasting.
PAUL SHAFFER, MUSICIAN: There really was no preparation, it was spontaneous.
CONAN O'BRIEN, T.V. HOST: Carson was the best show, Dave was the anti-show.
UNIDENTIFIED MALE: David Latterman.
JIMMY KINNEL, HOST, JIMMY KINNEL LIVE: I have more memories of the Letterman show than of my own life during that time from that time.
JAKE TAPPER, CNN JOURNALIST: Before Kimmel
UNIDENTIFIED MALE: It's on the chimp.
TAPPER: Seth, or Fallon. There was Dave, the king of quips.
LETTERMAN: Hi and welcome and to the damn show.
TAPPER: Stupid pet tricks, and outrageous pranks.
UNIDENTIFIED MALE: It's hard to say what his influence is not (ph).
TAPPER: But behind the scenes it wasn't all laughs.
BILL CARTER, AUTHOR: He was devastated, he was devastated.
UNIDENTIFIED MALE: NBC has no use for you people, wash out and get out.
LETTERMAN: Whoa hello, this is blackmail.
TAPPER: A late night legend signs off.
LETTERMAN: What this means now, is that Paul and I can be married.
TAPPER: A CNN special report, DAVID LETTERMAN SAYS GOODNIGHT.
LETTERMAN: I still have to do things like answer a viewer mail letters and here's one we received...
TAPPER: Viewer mail.
LETTERMAN: Here to begin, what's the deal with the sneakers? Well, we decided that this letter could be answered in person.
TAPPER: David Letterman's trademark bet (ph), it was 1986 and Steve O'Donnell was a writer for Dave's show.
STEVE O'DONNELL, T.V. WRITER: If we would get a letter that seemed provocative enough, we would seek them up.
LETTERMAN: I think this is the house right here.
TAPPER: Just one example of how Dave changed the game.
LETTERMAN: Let's go in up and see if Colin (ph) is home. We'll ring the bell here. It doesn't appear that anyone is home.
TAPPER: Five years into its run on NBC, Late Night With David Letterman was both clever and unconventional.
LETTERMAN: Can you show around the place and maybe show us some of your sister's stuff?
UNIDENTIFIED MALE: The brother showed up and he showed us the girl's room.
LETTERMAN: Let's take a look at the footwear. A lot of high heel shoes.
UNIDENTIFIED MALE: And then took us to where she worked at the mall.
LETTERMAN: Are you Colin Boyle (ph)?
COLIN BOYLE (PH): Oh my God.
UNIDENTIFIED MALE: And that was the kind of the model for spontaneous kind of guerilla T.V. making.
O'BRIEN: At that time that was electric.
TAPPER: Conan O'Brien could barely believe it.
O'BRIEN: It just wasn't something you ever saw, the idea of Johnny Carson going into someone's house.
Dave, you have to remember, he was wearing a -- it was all coming at from a completely different angle.
O'BRIEN: I think he did, yes.
The idea that he had walked out of the T.V. and into someone's room and is going through their stuff, it had huge impact on me.
TAPPER: A huge impact on pop culture, comedy, and all the shows that would come after his. Not bad for a boy next door from Indianapolis, Indiana.
His Dad Harry was florist, his Mom Dorothy, a church secretary. His mother later wrote a cook book filled with photos of Dave and his two sisters, and all American family who love a good laugh and watching television.
LETTERMAN: Our household was full of Arthur Godfrey productions.
And I can just remember being fascinated by -- when they would open the television impact of the simulcast, there was something about the microphone and the earphones and the equipment that I found fascinating.
TAPPER: Dave was a good player but at Broad Ripple High School not a great student.
LETTERMAN: I can remember doing so poorly my mom was very upset about it and she said, we're going to try to get you into a trade school. I was not able to keep up. And then one semester I took up public course and I realize this might be lifeline. I might be able to turn this into doing something.
TAPPER: At Ball State University, Dave turned it into his major.
CARTER: He decided to be a speech major in college.
TAPPER: Author Bill Carter has covered the T.V. industry for more than 25 years.
CARTER: He wasn't a student or anything, he joined the radio station, then he comes out of college and becomes a lower weatherman, and goofy weatherman.
LETTERMAN: The higher up have removed the border between India and Ohio making one giant state, personally I'm against it.
When the tropical storm becomes a hurricane I would wish her well and they didn't like that sort of thing because later it would go on to destroy millions and millions of dollars of property.
[21:05:00] TAPPER: Dave wasn't exactly suited for news but he was suited for comedy. So at 21-years-old he married his college sweetheart Michelle Cook and headed out to Hollywood.
CARTER: She was a steady lovely girl apparently, totally supportive of him. You know, his dreams at that point. A lot people didn't even know he had it first (ph), but, you know, he said he behaved badly right away because these young girls we're so smitten with him.
TAPPER: As Dave begun building an audience on L.A. standup circuit his marriage fell apart.
LETTERMAN: I just came back from reno (ph) state (inaudible) Jacuzzi though because when everybody got in the water we had to take (inaudible).
TAPPER: In 1975 Dave talked about the struggles of standup.
LETTERMAN: Say you go comedies (ph) and you do real well. And you get done and you're pretty exited for about 5 or 10 minutes and you think, wait a minute I just 18 drunk people laugh.
TAPPER: What was new about his (inaudible)?
CARTER: He was ironic I think is main thing. He had sort of a detachment. He's very cool and verbal.
TAPPER: By 1978 he hit the bit time.
UNIDENTIFIED MALE: Here's Johnny.
TAPPER: A guest spot with his long-time idol.
LETTERMAN: If your dog is constipated why screw up a good thing?
He was the biggest star in television and I was just a kid who kind of followed the beacon of his light coming out of Burbank. And to be on his show was endlessly nerve-wracking.
LETTERMAN: There was a fire in Laurel Canyon not too long ago and I lost like an entire (inaudible) you know. But you know paper burns and...
JOHNNY CARSON, T.V. HOST: Just like that.
TAPPER: But Johnny Carson fell hard for Dave.
CARSON: It's always a former house. Nobody buys an original house out there.
CARSON: Formerly owned by Dorothy Lamour's cousin or something...
LETTERMAN: Yes, I think Squeaky Fromme used to live in the place I...
CARSON: Squeaky's own place, yes.
CARTER: They could really banter. He become a protegee which, you know, was hard to do with Johnny.
CARSON: I have a feeling here, your shot at this show tonight, you're going to be working a lot outside of the comedy star.
LETTERMAN: Thank you.
TAPPER: And after just a few appearances, Dave went from guest...
UNIDENTIFIED MALE: Johnny's guest host tonight is David Letterman.
TAPPER: To guest host and became a network favorite.
UNIDENTIFIED MALE: It's the David Letterman Show live.
TAPPER: NBC execs we're so smitten in 1980 Dave got his own morning talk show. Veteran T.V. director Hal Gurnee.
HAL GURNEE, T.V. DIRECTOR: It wasn't fun to begin with, there was room for doing musical acts, anybody who would came in, it was like a sitcom, people come in through a door.
LETTERMAN: Welcome our very own staff member Rich Hall with gardening (ph) will be here.
GURNEE: It was wildly inappropriate for his style.
TAPPER: When we return, a devastating blow of David Letterman.
UNIDENTIFIED FEMALE: Mr. Letterman was sure we're doomed, like it was the end of everything.
UNIDENTIFIED MALE: David Letterman.
TAPPER: That's David Letterman, hosting a live morning talk show in 1980.
LETTERMAN: Make the thing make noises for us.
UNIDENTIFIED FEMALE: OK.
LETTERMAN: First of all why do you have this stuff?
TAPPER: And this was one of the few people who was watching.
O'BRIEN: Everything about it was a recipe.
LETTERMAN: An electronic wizard...
TAPPER: Conan O'Brien then in high school.
O'BRIEN: And it's very hard to explain that to people today. This guy was 180 degrees different from anything you had seen in that kind of format.
UNIDENTIFIED MALE: Would you like a tissue?
O'BRIEN: The whole thing felt wrong slash perfect. TAPPER: Maybe perfect for Conan but a poor fit for the time slot. After four months David Letterman was canceled. He thought his career was over.
CARTER: He was about as devastated as he could be. I think he remained for a lot of his career, consumed with self-doubt.
TAPPER: But NBC bras (ph) had other plans for Dave.
UNIDENTIFIED MALE: David Letterman.
UNIDENTIFIED MALE: Dave Letterman, come on everybody up. Everybody up.
TAPPER: In 1982 David landed late night airing at 12:30 A.M. right after his hero Johnny Carson.
CARSON: I love what you've done with the rec (ph) room, it's very nice.
TAPPER: A dream job and a time slot so late he really could do anything he wanted on air.
LETTERMAN: Right over there is the Today Show.
This prime-time program was my idea and I'm not wearing pants.
TAPPER: It was a completely unique talk show infused with Dave's sarcasm.
LETTERMAN: America's favorite summer time past time, destruction by gravity.
TAPPER: And wacky stunts.
SETH MEYERS, T.V. HOST: Throwing stuff off buildings, I just remember my friends and I watching that and thinking this is the greatest thing ever.
LETTERMAN: A turkey is a flightless bird, I don't think so.
TAPPER: Brand new territory for a talk show. Dave broke, he smash the forth wall, turning to his own team for inspiration.
LETTERMAN: What do you do with the jacket when I'm done with it?
UNIDENTIFIED MALE: I'll just add it do the big ball of sports coat.
LETTERMAN: Paul, good question, how exactly do you get out of there?
UNIDENTIFIED MALE: There really was no preparation, it was spontaneous.
UNIDENTIFIED MALE: We're just going to buff (ph) it. KINNEL: I love Paul, he always has the perfect reaction and I love the rhythm that they have together.
LETTERMAN: Serous again folks, what's his name. No it's Paul.
TAPPER: Fan leader and sidekick Paul Shaffer.
SHAFFER: You're giving me the one name...
LETTERMAN: What's that, what's that?
SHAFFER: The first shows, I don't, you know, have anything to say. So I asserted my self, you know, and just one day started talking. And Dave got a kick out of it.
LETTERMAN: You know Paul I used to do weather on T.V.
SHAFFER: You did because I used to be (inaudible) model.
They said, hey, you know, that was great. After the show he said do more of that.
I watched Johnny Carson and you are no Johnny Carson.
GURNEE: Sometimes we had a bigger audience than the Tonight Show.
TAPPER: And then he started a routine with you where he would talk to you...
TAPPER: ... during the show.
LETTERMAN: Hal? Hal? Hal?
TAPPER: Hilarious and innovative, everybody was along for the ride. There was guest cam and monkey cam.
KINNEL: They had 360 degree shows on where the show slowly over the course of the hour rotated, that was ridiculous.
UNIDENTIFIED FEMALE: We have achieved 180 degrees.
KINNEL: They did the show on plane, and I felt almost like it was somehow for me like they haven't said opened up (ph).
TAPPER: Letterman fan boy Jimmy Kinnel.
There's a picture I've seen from your 18th birthday and what was the cake?
KINNEL: Late Night with David Letterman and my mom made the cake, my mom had a Letterman, Letterman jacket made for me like the ones they have on the show. They didn't sell those. I played no sports and I wore Letterman jacket through high school everybody.
My license plates had L8 NITE. It's the most informative thing in my young life.
LETTERMAN: Please clear the hallway, you in a tie beat it will you? Thank you.
KINNEL: It just seems like it's such a waste of network television time, I love it.
UNIDENTIFIED MALE: They started a new kind of humor.
LETTERMAN: Get off the elevator, I'm serious.
And here's -- here's one of the smaller offices right there.
MERRIL MARKOE, FORMER HEAD WRITER: Carson had (inaudible) set we weren't supposed to (inaudible) that they shouldn't talk an announcer and they shouldn't be doing any monologue. I remember thinking, that's it, that's all the things we want to do, well that means everything.
TAPPER: Writer Merril Markoe was the brains behind much of late night, she and Dave we're involved professional and romantically for a decade.
MARKOE: Everything that I found in the phonebook that had made any kind of claim, I would go and ask them about it. Like if they said, just (inaudible), I would go, and what else do you allow?
TAPPER: Then she's send Dave there to harass them.
LETTERMAN: (Inaudible) what we have here.
UNIDENTIFIED FEMALE: Nothing.
LETTERMAN: What can you get in here?
UNIDENTIFIED FEMALE: What can you get in here? All these shades.
LETTERMAN: Markoe develops many of Dave's trademark segments.
MARKOE: Usually I think I'm ground zero for dog videos.
LETTERMAN: I just hope they don't let him drive after this.
TAPPER: That led to stupid pet tricks.
UNIDENTIFIED MALE: Play dead.
TAPPER: And the human tricks. And viewer mail.
LETTERMAN: Letter number.
O'BRIEN: My dream job was to work for David Letterman.
TAPPER: In 1985 Conan O'Brien tried to get a job as a writer on the show. O'BRIEN: It was between me and one other guy from Oklahoma, currently (ph) a mass murderer. But a very prolific mass murderer and they with the other guy and I was crushed.
O'DONNELL: I had a (inaudible) craziest job I ever had.
TAPPER: Steve O'Donnell though not a mass murderer got one of those coveted writing guest (ph).
O'DONNELL: And there's exhilaration of being a like a cult college dorm-type show but it wasn't necessarily clear that it would go on for a long, long time.
TAPPER: O'Donnell and the team came up with most of Dave's crazy getups.
LETTERMAN: We have 3,400 alka-seltzer tablets on this fine piece of clothing.
O'DONNELL: We did a bunch of stunts like since, that would partly inspired by Steve Alley (ph).
LETTERMAN: I got of food of pits (ph) on here and when I come out, I'll them among you folks, just smack your brains up.
TAPPER: And crafted Dave's classic top ten list.
O'DONNELL: On the first one, top 10 words that almost rhyme with peas.
LETTERMAN: And the number one word that almost rhyme with peas according to our poll is meats.
O'DONNELL: Yes, that was supposed to be absurd.
UNIDENTIFIED MALE: Two, one, ignition.
TAPPER: Off the charts absurd but arguably Dave's funniest material we're his remotes, pranks outside the studio.
LETTERMAN: I just want to ask you a couple of questions, what do you do for a living?
UNIDENTIFIED MALE: I'm a mail man.
LETTERMAN: Give me a favor, get into the fountain.
UNIDENTIFIED MALE: Get into it?
LETTERMAN: Come on get in, if you get fired I'll get you a job.
O'DONNELL: No one knew who he was because he was this guy on 12:30 at night. And I do remember when a lady suddenly went, wait a second I know you. UNIDENTIFIED FEMALE: Kevin McKay (ph).
LETTERMAN: That's right I'm Kevin McKay (ph), nice to see you.
We need authorization to drop off a fruit basket?
TAPPER: Dave begin taking remotes to a whole new level when he mocked his own network.
LETTERMAN: This is going to be fun to work with these people isn't it? To drop off a fruit basket we need paperwork.
CARTER: When he did the famous think and he took over and he brings a gift basket to them, the guy wouldn't shake his hand.
LETTERMAN: Nice to meet you.
[21:20:00] UNIDENTIFIED MALE: What is your name?
UNIDENTIFIED MALE: I'm going to ask you to turn the cameras off please.
LETTERMAN: OK, we just...
TAPPER: Do you feel like you're disobeying the bosses especially when he (inaudible) NBC?
GURNEE: Oh absolutely, that was important -- we we're all the same side...
UNIDENTIFIED MALE: I think he, you know, he hurt his own future that way. Here's Dave who wants to succeed more than anything else.
LETTERMAN: Dave, don't move body in driveway...
UNIDENTIFIED MALE: Here's the people who are going to make the decision and you are alienating them?
LETTERMAN: You bet it's a G.E.
UNIDENTIFIED MALE: David Letterman.
TAPPER: But the audience loved it. After a year in the air he was everywhere. Late night once coal pit (ph) become must see T.V. but Dave never relaxed.
MARKOE: Having been canceled once, he felt another cancelation was imminent. He just feel there was an axe over his head and he was waiting for it to drop.
TAPPER: Ahead the axe drops. The war for late night.
UNIDENTIFIED MALE: (Inaudible) can I speak to you for a second?
UNIDENTIFIED MALE: Will you people leave me alone, this is an experiment damn it, my stuff on the right side is tingling, it's tingling, do you what that means? It's working that's what that means.
[21:25:00] TAPPER: David Letterman could seemingly find humor anywhere.
And by the late 80s, all the cool kids wanted to hang with Dave. Including fellow coming Jay Leno who Jay Leno who would up with Letterman doing standup in the 70s.
JAY LENO, COMEDIAN: I'm no the kind of guy that brags, right?
O'DONNELL: Leno was our dream guest. Whatever was going on, in some weeks or months we go, well we got Leno next Thursday.
CARTER: That led to Jay getting the job as the permanent substitute host of Johnny because he's so good.
UNIDENTIFIED MALE: Here's Jay Leno.
UNIDENTIFIED MALE: You know we can get two shot here, we could actually sent the crew home.
TAPPER: Movie stars wanted in with Dave too but, they got no special treatment.
UNIDENTIFIED MALE: Please welcome Cher (ph).
O'BRIEN: He was suspicious of celebrity, you know, famously when Cher (ph) went on, he's not being the friendly, you're the greatest, you're the best, I love you, you're fantastic, you're Cher (ph). He's prodding...
LETTERMAN: Why finally after nearly 4.5 years did you decide to come on?
O'BRIEN: I thought that I would never want to do this show with you?
LETTERMAN: Now why, why -- because you thought I was...
CHER (PH): An ass...
O'BRIEN: It was like this electric moment, no one called Carson an asshole. First of all if you did you would disappear from the face of the earth.
TAPPER: Dave was on a roll. And then in 1992, a shocking announcement, Carson was stepping down.
CARSON: (Inaudible) good night.
TAPPER: To many Dave, after a decade of smash hit shows seemed to be heir apparent and joked with Johnny about it months before.
LETTERMAN: Would I like to have the show? Sure, yes.
CARSON: That's honest.
LETTERMAN: I likely to be looking at new poll stream now, you know.
TAPPER: Dave was all ready to inhering his hero's chair and his time slot.
GURNEE: That's what he was working for all those years, to do the Tonight Show.
TAPPER: But unknown to Dave and the rest of the world, NBC executives had another comedian in mind.
When did it come clear to Dave that he was not going to get this dream job?
GURNEE: They came to New York to talk to him and, we love you, we want to keep you where you are and he just says, that's unacceptable and I want out on my contract and walks out of the room.
TAPPER: Making it even worse, the comic NBC favored was Jay Leno who Dave had helped boost to success.
LENO: Did you ever tell you a little white lie that gets you into a lot of trouble?
TAPPER: Bill Carter wrote a best selling book about the battle for late night and he says NBC execs had doubts about Letterman.
CARTER: They thought, oh it's, you know, he's so experimental, can he do the Tonight Show, the Tonight Show format? And Jay, they had a guy who would do anything, anything they ask (inaudible) and they looked at that and said, why can't we have both? We'll give Leno this one and we'll keep Dave.
TAPPER: But Dave would have none of it and public jostling for the Tonight Show went on for months.
LETTERMAN: You know we we're on 12:30 we did OK, we did pretty well. I guess it was just that odd thing, NBC and myself, Jay Leon and myself and you had like an ongoing soap op (inaudible) strategy, big guy, the little guy, the, you know, the one guy who didn't get the job.
TAPPER: Ultimately Leno got the gig.
LENO: Now why would someone claim to be a (inaudible)?
TAPPER: Dave was crushed. CARTER: He was devastated, he was devastated. There's a lot of people who say that Dave was this wild creative comic and decides to become a mainstream comic. And Jay calculated very smartly what's -- he need to do, if you think about late night show at 11:30, Dave wants to win, it played out in an interesting way, Dave didn't play the game, Jay got the show.
LETTERMAN: We love it. Enjoy yourselves, I'll be right back.
TAPPER: Dave's relationship with NBC become fractured. But, all the other networks came accordant.
LETTERMAN: We went to Los Angeles, we had this meetings with these people and I think that -- what made the real different is, they would bring in a place of fresh fruit, and it was first rate fruits. And I think that...
UNIDENTIFIED MALE: That impressed you?
LETTERMAN: Not me but I think that impressed every other bonehead that came in, you know.
TAPPER: Ultimately he gets the most powerful agent Hollywood represents.
CARTER: Yes, that's where (inaudible) came up with this idea that, if it doesn't play at 11:30, there's a $50 million penalty, that's how they got around that.
CBC said, we're going to make you the signature star of the network. I mean, you know, you're going to be the guy for us.
TAPPER: Coming up, Dave rolls the dice.
GURNEE: He was worried about going to another venue, the CBC thing was about gamble.
LETTERMAN: I check this now with the CBC attorneys and legally I can continue to call my self Dave.
LETTERMAN: This morning, I wake up and next to me in bed is the head of a peacock. So I don't know...
TAPPER: Broadway is Ed Sullivan Theater.
LETTERMAN: It's a marvelous, wonderful as it is and we couldn't be happier to be here.
TAPPER: August, 1993.
GURNEE: The thing that spooked Dave more nothing else with the double bound, it was enormous.
LETTERMAN: Ladies and gentlemen, we have a wonderful program tonight, Bill Murray, Billy Jones...
TAPPER: Dave's first night on a new network.
SHAFFER: Welcome on Broadway, baby.
TAPPER: In a new time slot.
When the dust of the late night war settled, Jay Leno have the Tonight Show and Dave have a multi million dollar deal with CBS. It was a risky move.
CARTER: CBS did not have anything in their history of late night.
So, Letterman, in his first couple of months on the air was absolute can't miss television.
LETTERMAN: It's a joke, OK?
UNIDENTIFIED MALE: It's me, you jerk.
UNIDENTIFIED MALE: Every single night. He just killed it, killed it, killed it.
[21:35:00] LETTERMAN: Ladies and gentleman this is not a promo this is the actual show.
TOPPOER: Dave upped his monologue and added more A-list guests.
DREW BARRYMORE, ACTRESS: Would you like to do a dance for you?
TAPPER: But just Drew Barrymore who gave Dave an unforgettable birthday present.
LETTERMAN: Oh my God.
GURNEE: We've done a lot of my favorite reactions shoot and -- for some reason I thought it would be funny if she used the F-word over and over and over again, it got tiresome.
BARRYMORE: Actually, I brought something to like make a point.
LETTERMAN: OK. Good.
BARRYMORE: You are always -- use me on the show.
GURNEE: And then in the middle of all these -- the F-word. There was an elderly woman and her husband sitting in the audience and I just had a shot of her and got (ph) a big, big laugh.
LETTERMAN: Turn the volume down immediately she can't be stopped. There's something wrong...
TAPPER: Non stop laughs. Yet writer Steve O'Donnell says Dave never thought he was good enough.
O'DONNELL: I think it could be painful to people close to him, I have saved dozens of little notes he would write during the show and they alternate between I hate myself and stand by show and then he went stay at my show.
TAPPER: Even as he worried about his own success on CBS, Dave paid it forward just as Carson had done for him.
O'BRIEN: I'll give it a shot. All right, he should maybe put him away.
TOOPER: Conan O'Brien Brian was a virtual unknown. He replaced Dave on NBC's Late Night.
O'BRIEN: I was being pummeled to death on television every night.
I wasn't even on the air just a couple of months and Dave came on as a guest.
That was a huge deal.
When I first got this job, I came here to 30 Rock...
LETTERMAN: How did you get this job?
O'BRIEN: So, always indebted to him for that.
LETTERMAN: There for a free taco.
TAPPER: Dave delivered everywhere he went and for a couple of years, he was golden, going head to head with his old Pal at NBC at 11:30 and winning.
UNIDENTIFIED MALE: (Inaudible) the NBC (inaudible)...
TAPPER: That is until a shocking celebrity scandal in 1995.
A gigantic get when Leno landed Hugh Grant after the actor's arrest for soliciting a prostitute.
LENO: What the hell were you thinking?
TAPPER: That epic interview plus NBC's monster prime-time hits and Leno's own fine tuning of the show took a tool on Letterman's late show.
CARTER: It really hurt Letterman I think. And he -- became extremely difficult struggle for him to like counter all that moment at NBC.
LENO: If you want to influence Congressman, you got something full beer cans...
TAPPER: Jay Leno went on to win the rating is force for 15 years. Gradually Dave made peace with it.
LENO: He was more comfortable as the hipper, slightly spewed show with slightly spewed attitude than being at number one.
KINNEL: It doesn't matter what the ratings are. It really doesn't matter, the fact to the matter is. Dave is the best there ever was. Dave started something.
TAPPER: In 2000, Dave showed a much softer side after emergency heart bypass surgery and five weeks off the air, he returned giving a touching tribute to the hospital staff who helped him.
LETTERMAN: These men and women right here saved my life and...
KINNEL: When Dave shows his human his side. It's a real treat like "oh, what's going on here? Who was this person we didn't know."
TAPPER: The episode earned an Emmy nomination. A year later Dave's, after September 11th, Dave couldn't hold back his emotions.
We're told that there were zealots fueled by religious fervor.
SHAFFER: He was phasing and figuring how he is going to say.
LETTERMAN: And if you lived would be thousands years old without making any sense to you, would that make any goddamn sense?
TAPPER: Dave was the first Late Night host back on air.
UNIDENTIFIED MALE: He made it OK to start laughing again.
TAPPER: (Inaudible) also changed. In 2003, he and girlfriend Regina Lasko had a son Harry named after Dave's late father.
MEYERS: It's been really sweet to get to see these big moments in his life, from his heart surgery to the birth of the son and I think as his gone older, we got to know him a little bit.
LETTERMAN: Your life doesn't really begin in the important ways until you had to try (ph).
TAPPER: When we come back, a cheating scandal turns Dave's world upside down.
LETTERMAN: I have a little story that I would like to tell you and the home viewers as well. Do you like (ph) a story?
LETTERMAN: Thank you very much for being on the again. You know, it's been three years since the last time you're on the show and I will just say right off the top here, you look different than I remember you.
TAPPER: The Late Show, January 2009. O'BRIEN: Joaquin Phoenix was I think crazy.
PHOENIX: Why do you have them on?
LETTERMAN: I'm sorry? I'm sorry? What did you say?
PHOENIX: What do you gas (ph) them up with?
O'BRIEN: It was like watching a surgeon, a really good surgeon. It was better than that. I was named the surgeon. It was just watching a maestro.
LETTERMAN: What can you tell us about your days with the Unabomber?
KIMMEL: He told you without specifically telling you that he thought that person was nuts (ph). For me, when I see somebody on the show, I have a pretty good idea of whether he is going to light them or not. And it really influences me. He likes them, I like them. And if he doesn't like them, they're idiots.
LETTERMAN: And Joaquin, I'm sorry, you couldn't be here tonight.
TAPPER: More than 25 years in the biz and Dave still nailed it. And when Jay Leno left The Tonight Show a few months later...
LENO: We have just two more shows left to do, you know?
TAPPER: Dave crushed his competition for the first time in more than a decade.
[21:45:01] O'BRIEN: Ladies and gentlemen welcome to The Tonight Show with Conan O'Brien. Thank you.
TAPPER: There was much drama over at NBC with Conan O'Brien getting The Tonight Show and then Leno wrestling (ph) it back from him.
LENO: It's good to be home.
TAPPER: In 2012, David and Conan joked about the late night mess. Both of them deprived that their Tonight Show dreams by scheming Jay Leno.
O'BRIEN: He's getting a live feed in a satellite truck right now. He is watching every second.
TAPPER: And it was kind of like, here are two guys very successful, nobody should feel bad for them but they're both kind of been through the same, hellish experience because of this other guy.
O'BRIEN: Yeah. It was just -- it was one of those nights. It was a nice moment that comes along every now and then where everything lines up.
LETTERMAN: What's your relationship with Jay because you knew Jay before that he demanded that he get his show back?
O'BRIEN: I was assured none of this would come up tonight.
TAPPER: Dave was leading The Late Night pack when he joked about Sarah Palin's daughter fell flat.
LETTERMAN: One awkward moment for Sarah Palin at the Yankee game during the 7th inning, her daughter was knocked up by Alex Rodriguez.
TAPPER: Adding fuel to the fire, Dave had messed up and targeted the wrong daughter.
CARTER: He took just the daughter. I think, a lot of people thought and think that's over the line.
LETTERMAN: I told a bad joke. I told a joke that was beyond flawed.
TAPPER: But that joke was nothing compared to what came next that year.
LETTERMAN: I had a little story that I would like to tell you and the home viewers as well.
TAPPER: The 62-year-old host confessed to a cheating scandal soon after he and long time girlfriend Regina Lasko had tied the knot.
This is an embarrassing thing to admit because it wasn't just -- a kind of an open secret that he...
CARTER: He'd had...
TAPPER: He'd had some relationship with some women who worked on the show.
CARTER: Yes, and people on the show were aware of that. But I don't think that were aware on this one.
TAPPER: Dave shocking confession drew a pause.
LETTERMAN: I have had sex with women who worked for me on this show. Now, my response to that is, yes, I have. I have had sex with women who work on this show.
TAPPER: Dave's confession came after an extortion attempt by a CBS producer who demanded millions to keep hush Dave's affairs with staff.
LETTERMAN: And would it be embarrassing if it were made public? Perhaps it would, perhaps it would - especially for the women.
CARTER: The fact that he's has affair probably that's conventional but then, the guy wants up turn a blackmail man. And I think it's very, very Letterman that instead of he's paying this guy off, keep it quiet, he said, "No. I'm not doing that." And he went right to the cops.
LETTERMAN: I just want to thank the people at the Special Prosecution Bureau and the Manhattan District Attorney's Office.
CARTER: And this is a guy who hates humiliation, hates it.
TAPPER: The CBS producer pleaded guilty to attempted grand larceny and spent four months in jail.
A week after the scandal, Dave apologized to his wife on air.
LETTERMAN: My wife, Regina, she has been horribly hurt by my behavior, and when something happens like that, if you hurt a person and it's your responsibility, you try to fix it. So, let me tell you, folks, I got my work cut out for me.
TAPPER: Dave called this the lowest point in his life. The couple did reconciled and they are still together.
CARTER: Talk about electric television, it's just television like nothing else you've ever seen.
TAPPER: His ratings went up.
CARTER: He's ratings went up for that. But, you know, his ratings have never recovered much to the early days because he's always been playing from behind. And at some point, I think, he stopped feeling like he could win.
TAPPER: Coming up, Dave saving it so.
LETTERMAN: So, I was goofing around with my son Harry and I said, "Harry, what if I retire?" "Why would you retire?"
TAPPER: Dave and pop star Lady Gaga.
LADY GAGA, SINGER: Hello New York.
LETTERMAN: Nice to see you.
LADY GAGA: There was no stopping me so my mom was really supportive and, you know, I've been doing this for a long time and I had a lot of rejection and...
LETTERMAN: When I get fired at NBC my mom brought me here to CBS.
TAPPER: That was 23 years ago. Is weird that it's lasted this long it's 2015.
MARKOE: I think it's weird in the sense that he felt it was going to be canceled all the time, I heard about that endlessly and I would like to go back to that version of him and just go, what's wrong with you, you're going to be on for the rest of your life.
UNIDENTIFIED MALE: Here's Johnny. TAPPER: Or at least longer that his idol Johnny Carson.
CARSON: I bid you a very heartfelt good night.
TAPPER: In 2013 David Letterman became the longest running late night host in show business history.
LETTERMAN: My name is David Letterman the one fixed point in the ever changing late night sky.
TAPPER: He's had more than 18,000 guests.
LETTERMAN: Howard Stern.
TAPPER: Many of them regulars.
LETTERMAN: No. Bolmer. A little paint right in there. Yeah.
LETTERMAN: Julia Roberts.
JULIA ROBERTS, ACTRESS: You know, there was a time Dave when I asked you on a date.
LETTERMAN: Gentlemen turn off the cameras. Even the audience turn off the cameras. Jerry Seinfield.
UNIDENTIFIED MALE: I'm not going to make...
LETTERMAN: Yeah that's right.
UNIDENTIFIED MALE: Why would I? Their food is already here.
TAPPER: After more than 30 years on air for Letterman. His younger rivals are grabbing those coveted younger viewers.
[20:55:00] MEYERS: You know, not surprising anyone at this point but being David Letterman, like we all know what David Letterman is and yet he is still doing things you absolutely have to see.
LETTERMAN: It's too damn hot, there you go.
TAPPER: Late night observer Bill Carter has been seeing signs that Dave has been winding down.
CARTER: He really hasn't done of the bits that he used to do, you know, doesn't really doesn't go over personal. And there are people who would say, he probably should have left when he was closer to the peak. I think it's really been very hard for him.
LETTERMAN: When this show stops being fun I will retire 10 years later.
TAPPER: Then last April Letterman made a shocking reveal about a phone call he had with CBS Honcho Les Moonves.
LETTERMAN: When I said Leslie it's been great you've been great the network has been great.
SHAFFER: There was no indication until we were in the winds (ph). Can I just, you know, come with me over there and took me in a little alcohol and he said I've told the guy that...
LETTERMAN: I'm retiring.
SHAFFER: This is -- really.
SHAFFER: This is true -- this is you actually did this?
LETTERMAN: Yes I did.
SHAFFER: Wow. Well do I have do I have minute to call my cousin because.
Wow and then the next thing I know I was on stage, please (inaudible) what, I'm thinking what did I just hear and, you know, but that's -- it was just fast as that.
LETTERMAN: There's the bird look at that.
SHAFFER: It's here.
LETTERMAN: Look at that animal right there.
SHAFFER: Yeah it's beautiful yeah.
TAPPER: Dave said he's epiphany came after bird watching with his son Harry and then going to do his show.
LETTERMAN: So I get hold that night and I'm talking to my wife Regina and she said how was work I said, "Oh, well we think we identified the bird", and she says that's great who was on the show?
SHAFFER: I said I don't remember.
LETTERMAN: So, that's when I started thinking in terms of how long does a guy want to do a T.V show?
TAPPER: In 2012, Dave admitted battling depression with medication and even with meditation yet steady dose of fatherhood seems to be the most powerful elixir.
LETTERMAN: So I was goofing around with Harry and I said, Harry what if I retire then I would be able to spend more time with the family and Harry looked at me and said which part of the family?
ADAM SANDLER, COMMEDIANE: Oh boy here we go.
There simply is no better man than good old David Letterman.
LETTERMAN: Thank you for everything.
UNIDENTIFIED MALE: Thank you.
TAPPER: Dave celebrity friends however have been less understanding.
UNIDENTIFIED MALE: You know I have this number prepared for sometime to be honest Dave I wrote it for your funeral.
UNIDENTIFIED MALE: Believe me you're going to have nothing to do pretty soon.
LETTERMAN: Yeah I know.
UNIDENTIFIED MALE: This whole quitting idea...
UNIDENTIFIED MALE: ... is the stupidest thing I ever heard.
LETTERMAN: Oh my god.
CHER: And you're still an.
PRES. BARACK OBAMA, UNITED STATES OF AMERICA: Well I was thinking you and me we could play some dominos together.
TAPPER: Even President Obama gave David a heartfelt send off.
TAPPER: I think Dave will have the same kind of legacy that -- that Richard Pryor and George Carlin, I think that he is up there with those guys.
SHAFFER: You looked at all the other show and you see David Letterman's influenced.
UNIDENTIFIED MALE: How are you?
UNIDENTIFIED MALE: I loved his set.
UNIDENTIFIED MALE: We should do our show.
O'BRIEN: Dave not being on television just doesn't feel right, the next followed up by people pointing out to me that I'm the old guy now.
TAPPER: You're the oldest -- you're the one that's been on the longest.
O'BRIEN: I went from, "Who the hell is he" to, "He's still here?"
CARSON: Do you envision yourself 20 years from now doing your late night show?
SHAFFER: What the hell am I going to do with myself everyday at 4:00 P.M.?
TAPPER: So for Dave, what is going to do?
SHAFFER: Dave loves to get laughs.
LETTERMAN: You boys like a table or you want to sit at the bar.
SHAFFER: So, I wouldn't count him, you know, I would put him on a porch.
TAPPER: I know Dave would be the very last person to say he is better than Johnny but Dave is better than Johnny.
LETTERMAN: OK thank you very much Peter and our Arnold seriously thank you very much, I'm sorry about the chair they were supposed to fix it yesterday.
UNIDENTIFIED MALE: I do not envy whoever they find to put in that chair.
LETTERMAN: Good night, hope you enjoy it. Good night everybody.