super bowl boulevard, and our guests, marc lamont hill, an ben ferguson, and have fun at the game, and marc, fun at home watching from the couch with the good treats and snacks. fun to be with you. and thank you for joining us here. and jay leno, mr. comedy, begins right now. jay leno! >> reporter: america's late night leader. going out on top. >> a winner. that stays a legacy. >> reporter: the journey. from comedy club kid to the throne of king johnny. >> this man's name is jay leno. >> reporter: and the rivalries. >> i love letterman, and he is great. nip it in my heel, and make me work harder. >> reporter: and the triumphs. >> what the hell were you

thinki thinking? >> reporter: and the jay you didn't know. >> probably more sensitive than people would think. >> reporter: tonight, the blue collar guy -- >> it is the guy in the jean shirt and jeans, and that is him. >> reporter: who became an entertainment giant. jay leno, mr. comedy. >> and now, jay leno! >> reporter: the man of 1,000 monologues is down to the final cue cards. >> katy perry said when she was a young girl she prayed to god to have huge boobs, and so, atheists, your move! >> reporter: and jay leno departs the "tonight show" number one where he has been for years. admired. ♪ le me say that the jokes are funny ♪ >> by comedy cohorts.

>> and he has done a tremendous job all of these years. >> reporter: and the long time friends who know another side of him. tell me something that we don't know about jay? >> he is sensitive. if there is anybody in bad health, is everybody okay? can i refer you to somebody? let me know. >> reporter: and a guy that many say has not changed a bit in his rise up the comedy ranks. if he ends up on top, it is a journey that begins pretty much at the bottom. >> if you look the humor is there, because who is going to hang out with this guy. >> the first time i met jay was in new york city, and it was a 44th street and 9th avenue where the original improv was. >> and budd freedman knew him from those the days.

jay drives down to new york city over and over trying to break into comedy. >> and so the young man comes up to me at the club, and he says, excuse me, mr. friedman, but i have been waiting three nights in a row, i come down here from boston where i go to the school to go on, and i never get on. what do i have to do to get on? and i said, wait, you drive down from boston to new york and then drive back again when you don't get on? right. well, you are on next. >> reporter: and jay is an instant success. >> he was great and became a regular like that. he was special. >> you notice how all newsmen use the same metaphors. >> there are comics that have worked hard and honed their craft, and they are great. >> another senseless killing earlier today. >> and there are comics that are just born hilarious, and jay was

born hilarious. >> and who knew? >> reporter: 1973, jay graduates from emerson college and moves to los angeles. he performs anywhere and everywhere he can. ultimate li sh ultimately, he finds a home, once again at budd friedman's improv on stage on shows like this one, "freddy prinz and friends." >> it is fun to watch people drinking a bottle of wine. how much is that? $7. >> and sure, jay roast ed me a few times that. i were pretty funny. >> and that is a tacky club here the improv. and thank you very much. very nice. >> reporter: with the improv on the resume, he is booked into another prestigious venue, l.a.'s comedy store. >> and he had a night that was

jay and robin and pryor and elaine boozeler and billy crystal all in the same show. >> reporter: it is 1977 and jay's career is booming. then he gets the call. the "tonight show" with johnny carson wants him. >> and this young man's name is jay leno, and this is the first appearance on "the tonight show". >> reporter: that appearance with johnny is life changing. >> hi. i'm are the the united states. anybody from the united states? >> reporter: and that was like "america's hot wax" and comedy career on track, and off stage, leno finds love with a brunette named mavis nicholson. >> well, it works out great. >> we have great partnership.

>> reporter: they marry in 1980 and remaining together ever since. with mavis by his side, jay devote his spare time to his other passion. cars. >> when you work with your hands, you realize how easy it to make a living on television. >> jay is the guy in high school, he was tearing apart cars, and i mean, seriously tear thing apart the cars. >> it is fun to restore the cars and fix them up. >> he is a world class mechanic. >> i studied this for years and it is like i don't know how the turn a wrench. >> reporter: and by the mid-1980s, jay is hitting the stride. >> and doing some movies and tv. >> he was on top. he was probably the top standup touring in the '80s. he with was huge. >> reporter: he lands the first cable comedy special "jay leno and the american dream" and a regular guest on "the night show" and "late night with david

letterman." >> please welcome jay leno. >> reporter: it is 1985, and leno and letterman have no idea how often their paths will cross. >> i bid you a very heartfelt good night. >> reporter: and then the king of comedy steps down, and the heir apparent is on the way up. so what's better, bigger or smaller?

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♪ here's jay leno! >> reporter: august 1987, a milestone for jay leno. he's named permanent guest host of the "tonight show." >> can you believe the trouble over there in the soviet union. >> reporter: and subbing when johnny carson takes a break. >> and suddenly, we have fallen and we can't get up. >> reporter: and he is ready to take over in car sson retires, t

so is another guy. >> will you please welcome mr. david letterman. >> reporter: and letterman has his own show following carson on nbc. and then in 1991, comes this inevitable announcement, the king of late night will abdicate his throne. carson's bombshell. >> johnny carson has made it official. >> reporter: sets off a speculation of the successor, will it be letterman or leno? >> jay is sensational, and jay is the permanent guest host, but we have not made that announcement yet as to who the successor to johnny will be. >> reporter: secretly the decision has already been made. >> and really quietly, and with nobody in the business knowing it, they had a meeting absolutely private meeting with the nbc hierarchy and jay and

his manager, and they guaranteed him the show. and it was a huge blow-up. >> just how pissed off are you? >> not angry at jay leno about this? >> no. would i like to have the show? oh, yeah, sure. >> nbc also calculated that dave is very hard to work with. >> and we have no guests on the show, just jerky activity. er. >> and he did not play ball with them, but jay was much more accommodating and so jay did and he got the show. >> reporter: and his debut was may 25th, 1992, the middle of an election campaign. >> we know that ross perot has not said anything, and clinton has not inhaled anything.

>> reporter: and the early execution was an issue in the early days. >> yes, it was bumpy and the unlovely task of following in johnny carson's footsteps. >> i bid you a very heartfelt good night. >> and no way to say, oh, and then we moved smoothly to jay leno. >> big gun. i'll give you a refund on the ticket. >> i thought that he was off of the game a little, and he was not as con fi the dent. one thing is that he was too far from the audience. it felt like he was separated completely from the people. >> i never liked that distance of standing there with the lights in your eyes and hearing laughter and not seeing the faces. >> reporter: with the "tonight show" struggling, nbc toys with replacing leno with letterman, but in the end decides -- >> the host of the "tonight show" will continue to be jay leno.

>> what we are celebrating is that i have not been fired, all right. i already have the job. >> reporter: letterman bolts to cbs. setting up head-to-head competition against jay. >> and it is going to be a much better show. >> reporter: and leno tells journalists, he is cool with it. come on, it is going to be interest, and it is fun for you. >> and if you think about it, all i did was to take the summer off. >> and dave comes on and it is an absolutely sensation, and he crushes jay, crushes him. >> reporter: and the critics gush, too, but the fans are responding to jay including the signature headlines' bit. >> it is a high-rated part of the show, a nd jay has a great segment of the show. >> reporter: and another part, jay-walk jay-walking. >> to test people's knowledge of things in the news that they should know but maybe they don't. >> who are those two people? >> from the "love boat." >> from the "love boat"?

>> yeah. >> no. >> reporter: and then in the mid '90s, a battle for late night supre supremacy. >> and let me start with question number one. >> when hugh grant came on in 1995, and he had been busted with solicitation. >> and everybody was watching and anxious about what would happen. >> and what the hell were you thinkin thinking? >> he delivered that night, and it disarmed everybody, and it felt like, we can be relaxed with this guy, and the person who got busted with a prostitute, and relaxed with jay asking the questions. >> and although, have never been one to blow my own trumpet so to say, i think that it is -- >> and that hugh grant booking really did turn the tide? >> yes, everybody said, well, jay is good, and so it was very

crucial thing for him, and not that he had hugh grant, but he paid it off. he had a monstrous audience that night, jay. >> reporter: and that night, leno seizes number one, and pretty much, never looks back. as the years go by, memorable moments keep on coming. and one with the future governator. >> and this is why he needs to be recalled. >> it knocked everybody, including leno. >> and this is why i'm going to run for the governor of california. >> it was like one of the really great live tv moments that, you know, don't happen all that often. >> and jay wellcomes the president of the united states, barack obama. >> no sitting president had ever come on the show. >> and was jay nervous? >> oh, yes. everybody was shutdown and it was a huge, huge deal. >> let me say that kevin looks good in the suit.

>> thank you, sir. thank you, sir. >> reporter: and secure on top, he does not rest on the laurels. >> and everybody i have talked to say nobody outworks jay leno. >> i have seen it. he loves the work. >> reporter: but in 2004, nbc makes an unusual decision. >> i want to elaborate on an announcement made earlier today. >> reporter: and promised conan o'brien the "tonight show" in 2009. >> so they say, jay, you will be extend extended for five more years, and that is it, and then we will give the show to conan. and jay was hurt. >> reporter: hurt -- >> i am cleaning out the office today -- >> reporter: but ever the team players, he goes along. >> i am not spending enough time with my cars. and you know, i took the show over, and boy, there was a lot of animosity between me and dave and who is going to get it, and quite frankly a lot of what i felt, good friendships were

permanently damaged, and i don't want to see anybody go through that again. and good luck next week, my friend. >> reporter: next week, five years are up, but in the handoff, a fumble. it's a stationery and gifts store. anything we purchase for the paper cottage goes on our ink card. so you can manage your business expenses and access them online instantly with the game changing app from ink. we didn't get into business to spend time managing receipts, that's why we have ink. we like being in business because we like being creative, we like interacting with people. so you have time to focus on the things you love. ink from chase. so you can.

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you were the only choice. you were the perfect choice. >> reporter: may 2009. leno hands over the reins of

"the tonight show" to conan o'brien. >> thank you, everybody. thank you for watching. please give conan as much support as you've given me throughout the years. >> reporter: publicly the transition is positive. behind the scenes, tumultuous. nbc contractual agreements had guaranteed conan "the tonight show." but the network doesn't want to lose jay to a competitor. >> because he's number one. nobody takes the number one guy off the air. >> it's "the jay leno show." >> reporter: nbc's solution? give jay a show in primetime to save the network the higher costs involved in producing scripted dramas. and keep leno in the fold. >> it's a sound move. but for jay it was not a sound move because he was doing something weird. it was not something the audience had ever seen before. >> it's nice to be back. we've been off the air for three months. or as most people in hollywood call that, rehab. >> reporter: jay's 10:00 p.m. show premieres in september of 2009. >> and while we were off the government started this program to give people money for their old cars.

i made $5 billion. >> reporter: leno was back with his monologues and headline humor. but not all of his fans follow him. >> how bruising was it for jay to have to go to 10:00 p.m.? >> it was kind of bruising for all of us because we had to figure out what to do just like that. and we thought we were doing a pretty good job at 11:30. >> what do you think was the biggest challenge for him to succeed at 10:00? >> well, challenge is a word. >> reporter: a ratings challenge for the nbc affiliates, too. their 11:00 p.m. newscasts start taking hits from the weak lead-in. >> they were in a panic. so by october they were ready to remove jay if nbc didn't. >> ladies and gentlemen, welcome to "the tonight show with conan o'brien." thank you. >> reporter: meantime, conan's ratings aren't meeting expectations. >> it was a huge transition from jay leno to conan o'brien.

i mean, they're very -- stylistically they're very different. their personalities were different. jay was comfort food. he was macaroni and cheese. you knew exactly what you were going to get. >> leno had way more viewers. they'd lost the number one spot. >> reporter: in an effort to stop the tonight show viewer drop-off nbc asked leno if he'd be willing to do a half hour show at 11:30, pushing conan's "tonight show" to midnight. jay agrees. conan declines. >> then it became these camps. you know, the jay camp, the conan camp. >> just the back scenes had become front scenes. it just was a disaster. whb the curtain between reality and perception is torn, everybody feels uncomfortable. and that's a real problem for a host. >> reporter: the uncomfortable situation resolves when nbc pays conan and his staff $45 million to step aside. jay resumes his role as host of "the tonight show" in march of 2010. ♪ get back to where you once belonged ♪

>> when he came back, was he number one almost automatically? >> no. it was a hangover. and it damaged jay. >> what had happened ran absolutely counter to his brand, which is i'm not a hardball player. well, yes, you are. and of course they all are. i mean, you have to be a hardball player to succeed in that arena. >> reporter: jay takes the criticism he receives over the controversy in stride. >> yeah, you get beat up for a while. and you try to get your version of the story out there. and you know, with all the serious things going on in the world, this looks like fun. ooh. rich white people arguing. oh. you know, earthquakes and disease and rich white people arguing. it gets people's mind off things. so it's fine. >> reporter: and it points out? >> this was the decision nbc made. it wasn't the decision i made. you can't just nap your fingers and go my tv show failed, i want that one. it doesn't work that way. >> it's "the tonight show" with jay leno! >> reporter: leno now sets his sights on reclauming the late-night ratings lead.

in 14 months he's back on top in the ratings, a position he's maintained ever since. >> chelsea handler gave her a bottle of vodka and said you need this more than i do. that's how bad it was. >> reporter: those who worked alongside jay attribute his success and longevity at "the tonight show" to his work ethic and relatability. >> he's a hard-working guy. he's the hardest-working guy that i know. he was always gracious, always kind. you know, always had time to sign an autograph. what he shows, that regular guy aspect of him. it's the guy in the jeans shirt and the jeans. that's him. >> reporter: a regular guy approach that resonates. now nbc's betting on another good guy to carry the "tonight show" torch. ♪ tonight, tonight >> reporter: in a comedic duet last spring leno and jimmy fallon announce there's a new heir apparent. ♪ they think i can woo the demo ♪ >> and everyone is on board.

>> we're still friends, right? >> yeah. of course we're still friends. >> reporter: keeping it friendly this time around seems key to both jay and jimmy. >> jimmy has already learned a lesson from jay, which is, you know, nice guys can finish first. >> you don't want to miss any of this. >> reporter: and after 22 years and thousands of shows, leno is finishing as number one. >> what do you think jay's legacy is? >> two words -- a winner. that's jay's legacy. he, against people's expectations, always won. >> if you want to succeed in life, all you have to do is go to jay leno university. you could take a punch. the guy can take a punch. you know, he may go down, but he gets right back up. >> reporter: as for what jay will be up to next? >> whatever happens with jay, i want it to be something that he enjoys doing, something he wants to do. >> porn done by people in their 70s and their 80s. i'm 63, and i can't even keep

hosting this show. i'm going to japan. i'm going to go to japan and do porn. that's what i'm doing! >> reporter: still drawing the laughs. it's a good bet this mr. comedy just may show up at a club near you. >> thank you. >> thank you. nice to have you all here. -- captions by vitac -- www.vitac.com there's the beatles! ♪ >> nothing but a bunch of british elvis presleys. >> it's not true, it's not true! >> when the beatles arrived, from then on a thousand different things arose. ♪ glad all over >> is it a sex thing or -- >> it's sexual. >> yeah. >> completely. ♪ my father was a >> there is a desire to get power in order to use it for good. ♪ how does it feel >> pop musicians in today's generation, they can rule the world.