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CNN Special Report-20150523-23:48:00

>> this is a guy who hates humiliation. >> the cbs producer pled guilty to attempted grand larceny and spent four months in jail. a week after the scandal, dave apologized to his wife on air. >> my wife regina has been horribly hurt by my behavior. and when something happens like that, if you hurt a person and it's yurs your responsibility, you try to fix it. so let me tell you, folks, i got my work cut out for me. >> dave called this the lowest point in his life. the couple did reconcile and they are still together. >> talk about electric television. it's just television like nothing else you've ever seen. >> his ratings went up. >> his ratings went up after that. but you know his ratings have never recovered much from the early days because he's always been playing from behind. and at some point i think he stopped feeling like he could win. coming up, dave.

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CNN Special Report-20150523-23:38:00

think. it became an increasingly difficult struggle to counter all of that momentum at nbc. >> if you want to influence a congressman, you have to send him a full beer can. >> jay leno went on to win the ratings war for 15 years. gradual gradually, dave made peace with it. >> he is more comfortable as the hipper, slightly skewed show with a slightly skewed attitude and being at number one. >> it doesn't matter what the ratings are. it really doesn't matter. the fact of the matter is dave is the best there ever was. dave started something. >> dave dave dave dave dave dave dave! >> in 2000, dave showed a much softer side after emergency heart bypass surgery and five weeks of ott off the air, giving a touching tribute to the hospital staff that helped him. >> these men and women right here saved my life. >> and when dave shows his human side, it's a real treat. you're like, oh, what is going on here, who is this person we

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CNN Special Report-20150523-23:12:00

>> conan o'brien, then in high school. >> 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. >> would you like a tissue? >> thank you. >> the whole thing felt wrong/perfect. >> 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. >> he was about as devastated as you could be. i think he remained for a lot of his career consumed with self-doubt. >> but nbc brass had other plans for dave. >> david letterman! >> dave letterman, come on, everybody up. >> in 1982 dave landed "late night" airing at 12:30 a.m., right after his hero johnny carson. >> so that's what they're doing. >> a dream job in a time slot so late you really could do anything he wanted on air.

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CNN Special Report-20150523-23:39:00

didn't know? >> the episode earned an emmy nomination. >> the year later, the september after the 11th, he couldn't hold back his emotion. >> i was in the makeup room with him. he was pacing and trying to figure out what he would say. >> if you live to be a thousand years old will that make any sense to you? will that make any goddamn sense? >> letterman was the first late night host back on air. >> he made it okay to start laughing again. >> fatherhood also changed him. >> in 2003, he and his girlfriend had a son harry named after dave's late father. >> it's been really sweet to get to see these big moments in his life, from his heart surgery to the birth of his son and then i think as he's getten older we got to know him a little bit. >> your life doesn't really begin in the important ways until you've had a child. when we come back, a

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CNN Special Report-20150523-23:36:00

and i had a shot of her. it got big, bill laughs. >> turn the volume down immediately! she can't be stopped. >> nonstop laughs. yet writer steve o'donnell said dave never thought he was good enough. >> i think it could be painful for people close to him. i have saved dozens of little notes he wrote and they were like i hate myself and standby show. he would underline that. >> even as he worried about his own success on cbs, dave paid it forward just as carson had done for him. >> you better be as good as letterman! >> i'll give it a shot. >> he should maybe put him away. >> conan o'brien was a virtual unknown when he replaced dave on nbc's "late night." >> i was being pummelled to death on television every night. >> hey, hey. >> we'd only been on the air just a couple of months, and dave came on as a guest.

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CNN Special Report-20150523-23:34:00

this morning i wake up and next to me in bed is the head of a peacock. so i don't know. >> broadway's ed sullivan theater. >> it's a marvelous, wonderful edifice, and we couldn't be happier to be here. >> august 1993. >> the thing more than anything else, it was the double balcony, and it was enormous. >> ladies and gentlemen, we have a wonderful program tonight, bill murray, billy joel. >> dave's first night on a new network. >> welcome broadway, baby. >> in a new time slot. >> when the dust of the late night war settled, jay leno had "the tonight show" and dave had a multimillion-dollar deal with cbs. it was a risky move. >> cbs did not have anything in their history of late night. so letterman comes on, and his first few months on the air was absolute can't-miss television. >> it's a joke, okay? >> it is me, you jerk.

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CNN Special Report-20150523-01:54:00

night host in history. >> the one fixed point in the ever changing late night sky. >> he's had more than 18,000 guests. >> howard stern. >> many of them regulars. ♪ >> a little thing right in there. yeah. julia roberts [ applause ] >> you know, there was a time, dave, when i asked you on a date. >> turn off the cameras. clear the audience, turn off the cameras. >> after more than 30 years on air for letterman, his younger rivals are grabbing those coveted younger viewers. >>. ♪ i want to rock right now >> he's not surprising anyone at this point by being david letterman. and yet he's still doing things

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CNN Special Report-20150523-23:54:00

many of them, regulars. >> no! >> a little thing right in there. yeah! >> julia roberts! >> you know, there was a time, dave, when i asked you on a date. >> wait a minute, turn off the cameras! clear the audience. turn off the cameras! >> jerry seinfeld. >> i'm not going to mexico. why would i? their food is already here. >> after more than 30 years on air for letterman, his younger rivals are grabbing those coveted viewers. ♪ i want to rock right now >> you know, he's not surprising anybody at this point by being david letterman. we all know what david letterman is. yet he's still doing things you absolutely have to see. >> it's too damned hot! there you go! >> late-night observer bill carter has been seeing signs that dave has been winding down. >> he really hasn't done any of the bits he used to do.

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CNN Special Report-20150520-05:55:00

on air for letterman, his younger rivals are grabbing those coveted viewers. ♪ i want to rock right now >> you know, he's not surprising anybody at this point by being david letterman. we all know what david letterman is. yet he's still doing things you absolutely have to see. >> it's too damned hot! there you go! >> late-night observer bill carter has been seeing signs that dave has been winding down. >> he really hasn't done any of the bits he used to do. he doesn't really -- he doesn't even go to rehearsal. there are people who say he probably should have left when he was closer to the peak. but i think it's really been very hard for him. >> when this show stops being fun, i will retire ten years later. >> then, last april, letterman made a shocking reveal about a

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CNN Special Report-20150520-05:38:00

letterman's late show. >> it really hurt letterman and it became an extremely difficult struggle for him to count all that momentum at nbc. >> if you want to influence a congressman, you have to send him a full beer can. that's not -- >> jay leno went on to win the ratings wars for 15 years. gradually, dave made peace with it. >> he is more comfortable as the hipper, slightly skewed show with the slightly skewed attitude than being at number one. >> it doesn't matter what the ratings are. it really doesn't matter. the fact of the matter is, dave is the best there ever was. dave started something. >> 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. >> these men and women right here saved my life. >> and when dave shows his human

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