So back in the day Carson was thinking about hanging it up, hit the 25th Anniversary and call it. To the point NBC began making a shortlist of replacement hosts. They probably didn’t need to do that, as circa 1986 the only plausible replacement was Letterman. NBC wasn’t in love with then-guest host Joan Rivers, Jay Leno spent his time with Letterman, and Carson preferred Letterman.

IOTL that shortlist of ten names didn’t include Joan Rivers so she went off in a huff to host a rapidly failed talk show and Carson banned her lifetime style from The Tonight Show—both Leno & O’Brien (& Leno) would honour Carson, Jimmy Fallon of course put her on twice. Carson had no problem with competitors, he was just incredibly angry that she hadn’t talked to him.

Carson destroyed her, reinvigorated by the competition. Just in time to face off against Arsenio Hall, who could have been a much bigger player if Fox hadn’t screwed things up. But you’ll have to wait and see if @Brainbin carries through on that timeline he was working on.

But what if the shortlist included her name?

In that case Rivers doesn’t bail hard, she sticks around because every comic is obsessed with The Tonight Show in that era. And the mere chance to host it is everything. Most importantly it means Carson decides to hang it up. Yes obviously it would probably be Letterman, but it might not be—more importantly what happens? Who follows The Tonight Show? Heck it might be Leno, heh.
(The board talked about Carson replacements here.
 
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Or, here's another WI: WI Rivers manages to talk to Carson before she goes off to Fox? IMO, this is what really angered Carson about what she did; not that she left (look at how Carson treated Alan Thicke (and his other competitors) after their own failures) but that she left without telling him. Carson was a good and talented TV personality, but he could be a real bastard sometimes...

Getting back to your question: yeah, Letterman probably hosts it. Rivers might get a show following Letterman ITTL. One thing not going off to Fox would do is to lengthen the life of her husband (and Melissa's father) Edgar Rosenberg; he committed suicide after Fox had fired him and Rivers and he and Rivers had separated. Rivers always thought he had depression brought on by an earlier heart attack, which was worsened by the failure of Joan's show and the subsequent firing (not to mention their separation; if she doesn't leave, the separation doesn't happen)...
 
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@Unknown
I’m down with your variant. Might even work better: Rivers leaves on good terms, Carson is bummed he doesn’t get to work with his friend instead of angry, and calls it.

Garry Shandling might be chosen, if his mental health was good enough.

Oooh, you’re in for a treat with this great profile by Amy Wallace.

Shandling was approached by NBC to host a real talk show in David Letterman’s old spot. He remembers talking the idea over with Roy London, who had worked on Sanders, advising on scripts and occasionally directing. “I would say, ‘Roy, can I grow as an artist going on TV every night?'” The question was its own answer. He turned the offer down.

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Let’s throw some work on possibilities. I like @Unknown version. So let’s say Joan Rivers is a mild success at Fox? I can’t imagine her clearance rate is over 50% though.

Letterman gets the Tonight Show, in 1987 that’s going to be huge especially with Markoe crafting the foundation and all the work he had to lose when he went to CBS IOTL. I know NBC is quite interested in Jay Leno, Jerry Seinfeld, and indeed Garry Shandling (though with Carson retiring there’s only a single year of guest hosts after Rivers). All three men have upsides/downsides of course. Including not really wanting to do a show a day in the latter two’s case.

Here’s the thing though. If you put Jay Leno on the air after Letterman the show will be terrible until Helen (his then-manager, a pretty messed up abuser who did get him The Tonight Show IOTL) implodes. That took three months, but it could take longer on the less powerful Late Night. It could even take long enough / go worse enough that the Leno is out. On the other hand maybe it goes faster/better?

If not Leno then who?

And also how well does Letterman do longer term? Moving to Burbank, way more stress with network executives West Coast faction who dislike him (the East Coast faction in New York liked him, but they’re far away now), he’s going to break up with Markoe I assume pretty fast, well pretty soon everything in NBC late night could be falling apart!!!

And here we come to Fox, CBS, and ABC. All wanting late night success because of the cash. But I need to reread a book to discuss more on that lol.
 
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What if Leno implodes with Helen in the later spot? Seeing how well Arsenio is doing would NBC give Richard Pryor a shot? Would he be up for it?
 
Let’s throw some work on possibilities. I like @Unknown version. So let’s say Joan Rivers is a mild success at Fox? I can’t imagine her clearance rate is over 50% though.

Letterman gets the Tonight Show, in 1987 that’s going to be huge especially with Markoe crafting the foundation and all the work he had to lose when he went to CBS IOTL. I know NBC is quite interested in Jay Leno, Jerry Seinfeld, and indeed Garry Shandling (though with Carson retiring there’s only a single year of guest hosts after Rivers). All three men have upsides/downsides of course. Including not really wanting to do a show a day in the latter two’s case.

Here’s the thing though. If you put Jay Leno on the air after Letterman the show will be terrible until Helen (his then-manager, a pretty messed up abuser who did get him The Tonight Show IOTL) implodes. That took three months, but it could take longer on the less powerful Late Night. It could even take long enough / go worse enough that the Leno is out. On the other hand maybe it goes faster/better?

If not Leno then who?

And also how well does Letterman do longer term? Moving to Burbank, way more stress with network executives West Coast faction who dislike him (the East Coast faction in New York liked him, but they’re far away now), he’s going to break up with Markoe I assume pretty fast, well pretty soon everything in NBC late night could be falling apart!!!

And here we come to Fox, CBS, and ABC. All wanting late night success because of the cash. But I need to reread a book to discuss more on that lol.
I'd say Leno doesn't get the gig, he doesn't have the contacts or clout for it yet and this isn't a Conan-in-1993 situation, they aren't desperate to find a replacement. Shandling turns it down... but Jerry Seinfeld? We're about a year away from NBC approaching Seinfeld for a sitcom development deal (November 2, 1988). He'd already done a special for them. They knew him. I'd say he's definitely a likely candidate. And he could still approach Larry David to help him run the thing, since he has lots of variety-sketch comedy experience (at SNL and Friday's). So something satirical like Seinfeld or Larry Sanders only it's an actual talk show. Really off the wall - basically experimental even by Letterman standards. It's not "safe" and NBC would like "safe". But it's a good way to keep up Letterman's anarchic spirit since he has to go "mainstream". I can see it crash and burn, but it might be fun.

But don't forget Later began airing in 1988 IOTL, about this same time frame. Bob Costas was the first host and he'd probably be a prime candidate for Late Night IOTL, if the network decides to return to the Tomorrow format. Perhaps it was the success of Later that inspired Letterman himself to build The Late Late Show around Tom Snyder (along with it being a kind of a mea culpa for his role in getting Tomorrow cancelled in the first place). Snyder still works for NBC, maybe they just bring him back altogether.

So we're looking at a return to the 1970s-style schizophrenic late night schedule in that circumstance. The Tonight Show with David Letterman at 11:30, and then Late Night (possibly renamed back to Tomorrow) with Bob Costas or Tom Synder. Since Later began running in 1988 IOTL, we probably see it coming on after Costas/Snyder. Jerry Seinfeld getting a 1:30 timeslot where he and Larry David can basically air whatever they want? That sounds like fun. It butterflies Seinfeld, of course, which... well, I've written pop cultural TLs before, I've made my share of enemies.

11:30 - 12:30: The Tonight Show with David Letterman
12:30 - 1:30: Late Night with Bob Costas (or Tom Snyder)
1:30 - 2:00: Later with Jerry Seinfeld
 
@Corjomc
I think it’s too late for Pryor—a couple years earlier I’d say he has a shot somewhere though (perhaps more like 12:30 though)

@Brainbin
One thing to note is that IOTL Seinfeld has repeatedly deconstructed the talk show while on one. Explaining how pre-show interviews set up all the stuff you’re watching now for example. So that in of itself is a solid premise for a talk show—and very different. Can Seinfeld and Larry David do this for four nights a week and forty-four weeks a year? [1] And indeed NBC loved him. They didn’t sign a sitcom deal with him, that’s just what Seinfeld himself was working on, they signed a holding deal to take him off the market. They would have signed him if Seinfeld had said anything.

Letterman knew exactly how to transition to 11:30, he just never actually told the NBC executives that. Here he does, because he has to as the leading contender. So that means NBC will have a solid idea of what to expect and can position Late Night accordingly. Brandon Tartikoff played it super-safe with Carson, never pushing him, and I think that would extend to Late Night. They’d want someone like Letterman but different but hip and warm and a good interviewer but also funny etc… (oh network notes) and a stand-up comic is likely. So I’d go the other way around: Seinfeld takes Late Night, Costas or Sydner or maybe both do a show after (reduce Late Night to a half hour, have four shows?)—this all taking place in 1987 instead of 1988 OTL. As time rolls into the evening the late night audience gets younger so NBC would very much want hip/cool directly after Letterman.

Sadly times should probably be 11:35 etc… Carson had the clout to keep Tonight at 11:30 until the Gulf War, Letterman would not. Sure this is before that news (when some affiliates wanted to push Tonight to midnight!) but the war over those five minutes had already begun in earnest. After Carson I bet it relaunches at 11:35.

Carson IOTL retired before his actual 30th anniversary to hit May sweeps and skip the doldrums summer. Would he do that, meaning he’s done May 1987? Or would he decide to go official, maybe take the summer off and then do a two month long victory lap kinda thing September-October? NBC would far prefer the latter scenario, allowing them to launch November sweeps for the new team.


[1] Carson himself was down to three nights a week and thirty-seven weeks a year—you see why guest hosts had such a high profile. Letterman did four nights a week on Late Night, five nights a week (to start) on Late Show—forty-four weeks long and Leno did more. If Letterman had Tonight I suspect four nights a week would remain standard on NBC late night.
 
Carson: I'm torn. If Carson doesn't want to work through the summer of 1987, he won't, period. And as you say, the man was already down to three days a week. He doesn't strike me as having the greatest work ethic. IOTL, Leno took over right on Carson's heels, but as you point out (and unlike IOTL), NBC basically has a whole new late-night schedule they have to fill. The problem is, an absence of several months does create an opening for competition...

Competition: Rivers was fired from FOX in May of 1987 IOTL - so it really depends on what you want to do with her. Having Carson outlast one last rival before his retirement feels like a victory lap. Arsenio taking over for her with no competition for several months gives him a unique opportunity.

There's also CBS, which began airing The Pat Sajak Show in early 1989 IOTL. With Carson retiring, they might sense an opportunity to enter late night earlier ITTL. Apparently the CBS executive who championed the show, Michael Brockman, had been planning to launch a show hosted by Sajak as early as 1986 IOTL, so we're very likely seeing Letterman with competition on two fronts in the fall of 1987.

Sajak leaving the daytime Wheel earlier means they pick a more competent host to replace him than their OTL choice, the former football player Rolf Benirschke (who had no broadcast television experience whatsoever), as he did not retire from pro football until December of 1987 IOTL. Keeping the daytime Wheel on the air has huge repercussions for the fate of daytime game shows.

This gives NBC less luxury to let Tonight go on hiatus for several months. By fall of 1987, the situation will be as follows.

NBC: The Tonight Show with David Letterman
CBS: The Pat Sajak Show
FOX: The Late Show with Joan Rivers (or Arsenio Hall, or somebody else)

Along with, of course, Nightline on ABC.

Letterman: Does Shaffer move with him to Beautiful Downtown Burbank? If not, who replaces him as the second banana? Letterman may not have had a traditional "sidekick" like Ed McMahon, but Shaffer very much filled the role de facto.

Does Letterman use guest hosts like Carson (and Paar) did? I say yes - and I love the irony of Leno (an occasional guest host for Carson) being promoted by Letterman to permanent guest host (everyone's favourite triple oxymoron). The two were good friends, after all.

Agreed that he is bumped to 11:35. One question: does NBC manage to rope him into going back to 90 minutes? It was, after all, Carson's clout which got them to knock The Tonight Show down to an hour in 1980, and since Letterman is taking over for Carson it's not as though they're pushing anyone back. Worth noting: Sajak ran for 90 minutes for most of his run.

Seinfeld: You sold me on him getting Late Night. I'm having a lot of fun imagining this show: influenced by SNL, Friday's, even The Muppet Show to an extent... along with Larry Sanders, Seinfeld, and Curb your Enthusiasm. I see Larry David as a "character" in the show, much like Fred de Cordova on Tonight, always just offscreen but (unlike de Cordova) fully voiced - similar to many of his "appearances" on Seinfeld. Any guest "interviews" will have lots of improv like Curb (or the short-lived Life with Bonnie) where the guests are self-parodying. Jerry being a gadfly much like his Seinfeld persona is easy to imagine. "So, in the pre-interview, you asked us not to discuss your divorce. Why is that?" (Obviously this is all cleared with the guests beforehand in the real world.)

I see a "second banana" character for Jerry to bounce off of - as in Seinfeld, a stronger character actor who can "support" him if need be. For contrast he'll probably be older, less "hip" - more Arthur Treacher than Ed McMahon. (And not just because Seinfeld mocked the Merv Griffin Show once, although that helps.) Someone who is very combative with Jerry, like a Newman. They can't stand each other "off camera". There's no house band; the music is provided by synths played by (of course) Jonathan Wolff.

One relatively "straight" aspect of the show is that the guest comedians are allowed to give "straight" sets - one of Seinfeld's few truly admirable qualities is his support for up-and-comers. Usually he'll play "jealous" though because their material is invariably edgier than his, and he's worried they're showing him up. Seinfeld is also "jealous" of Letterman but good at "hiding" it, unlike David's character. ("Letterman is killing us, Jerry, he's killing us!")

By the time the first year is up the show is so dense and convoluted and full of in-jokes (like Seinfeld) that it's a thing of beauty. And to everyone's surprise, at the Emmys, it wins the Writing Emmy over Letterman and all the other late-night shows. (The Emmys are notoriously stodgy in many ways but surprisingly they're very cutting-edge when it comes to late-night and variety and always have been.)

Later: You can confirm this, but I heard Snyder was offered a chance to continue hosting Tomorrow if he agreed to be bumped to after Letterman (yes, this was going on even back then). He declined and the show was cancelled. If this is true, I don't see him coming back at 1:35 seven years later. So Bob Costas gets Later and it basically plays out as IOTL, as a successor to the Tomorrow legacy.
 
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If NBC is worried about the competition for a few months getting a head start on Letterman, perhaps they use the summer months to test a few things. Johnny Carson is gone, but they can pull something of a Seinfeld as you say with the pre-interview interviews and make it like a pre September planning stage. Bob Costas could appear and do some things too, with some comedy about his transitioning from Sports to other stuff.

This would allow Letterman to take more time off. There could be some in jokes developing because he uses not only Leno but Seinfeld as his guest hosts in the summer months and it can appear to the audience like they are doing things on the fly when they are not. A little bit of 4th wall breaking about letting the audience in on the fun and you could have people tuning in just to see what they will do.

Then, in the fall, what they have been leading to all along develops. Letterman, who has been doing one night a week in the summer with numerous skits about his moving out to California, takes over permanently though he has really been doing so since June.

Remember, too, that Johnny Carson would occasionally send Letterman jokes. He would honor the man by making a golf club swing motion each time he used one. With Carson's permission there could be some sort of Johnny Carson seal of approval every time they decide on something that summer and it looks good, or maybe not. Carson was a very private man if I recall and he might prefer to just have the golf swing thing be the only memory.

This would be helpful to because if I recall correctly there was a writer's strike the next year. Hmmm, in looking I see it was 5 months but I seem to recall Johnny Carson being back by late April so maybe they made do with their own stuff? If they start in June they will have had 9 months before the strike so it probably wouldn't hurt them comedy wise. But, I really don't know how such things affected anyone in this area.
 
@Brainbin
If you think Johnny Carson had a bad work ethic watch out for Pat Sajak!!! Of course the real reason Carson did three nights a week was because he was headlining comedy shows elsewhere, he had a great work ethic because he was a crazy person—just didn’t care about Tonight much anymore and Tartikoff never pushed.

Perhaps if NBC hands Carson a years contract (even if of course NBC regains ownership of Tonight) of 20 million dollars for two months as launch insurance…

IOTL David Letterman surged to something like a 6.7 rating (handily crushing Leno) in 1993/4—of note is that has a 70% clearance rate [1] from low quality spectrum CBS affailiates vs 100% for Tonight on quality channels. ITTL? Almost certainly higher. Carson was getting a 6.6 rating in 1985/86, 7.0 in 1986/87 as he enjoyed crushing Rivers. This is when NBC was worried about his getting older audience with declining demographics. Carson had a 7.9 rating in 1974. I think that’s a solid figure for Letterman with quite a bit better demo numbers. Heck a 9.5 number would be both plausible and nuts, and I’m willing to make the case for even higher. [2]

So Joan Rivers with an unknown clearance rate (2.6 rating IOTL), Sajak ditto (3.0 IOTL)—both dead in the water against the most dominating figure in late night with ratings not seen since the glory days of Carson. Sajak in particular did absolutely nothing IOTL to try and save his show. 1987 then sweeps out the competition.

I’m almost certain 90 minutes is off the table. Letterman would probably toss a million bucks of salary at that, lol. He won’t win the 11:30/11:35 battle, he doesn’t get to own the show, his salary is a lousy five million, but he would lose his mind at having to do 90 minutes heh. On the other hand if/once Letterman burns out the dude that follows him might be doing 90 minutes… (the economics are compelling after all, adding 30 minutes costs almost nothing against the increased ad rates they’ll get for the back half hour vs different host).

So Late Night with Jerry Seinfeld gets a monster lead-in, and that in turn boosts Costa (as I agree he does something akin to OTL but ITTL with millions more viewers with plausible butterfly effects all over America), and NBC remains the dominant force in late night. Essentially everyone mounts a challenge and everybody (except Nightline) crashes and burns hard.

Yeah that sounds right/brilliant/hilarious. Seinfeld as a talk show host is a combo of Jay Leno and Garry Shandling and Larry David and I think it would be amazing. I’d have to think about the nemesis, but Michael Richards—who knew Larry David via ABC’s Fridays—is plausibly perfect. Kramer style pratfalls on a talk show—yes! (Physical humour would present the contrast, in this scenario, where Richards wins bizarre Larry David scripted conversations with Seinfeld, everyday objects like chairs prove his undoing.)

Of course Jay Leno is going to be premmenient as a guest/permanent guest host on Tonight—anything could happen! Leno unlike Letterman worked the political game hard.

(I forgot the Jay Leno Show of 1986. I think without that he might have gotten Late Night in 1987 ITTL, with it no way.)

@DTF955Baseballfan
Straight up sounds solid. Of course Carson would still fax in jokes, I think Letterman would stay as subtle as OTL… but I think there’s a Carson appearance at some point where the two men reveal it. Maybe whenever Letterman is on the way out?

Probably Leno, Letterman, Seinfeld, and maybe Joan Rivers comes back for the summer—as in TTL she’s on good terms with Carson & Fox is cool hoping for a boost in her ratings.



[1] The clearance rate is how many affailiate channels—as opposed to the limited number allowed to be owned & operated by the networks themselves—broadcast the show on time. The Tonight Show had a 100% clearance run for the time of Carson and Leno, Letterman on the other hand only got 70% to broadcast on time (the rest thirty minutes later) on and still crushed at launch.

[2] My 9.5 rating is simply 6.7 extrapolated to a 100% clearance, not even counting the vastly different circumstances—higher is within reach. One Letterman prime-time special NBC IOTL reached a 17 rating. His opening Late Show did a 10.9 (32 share) with said 70% clearance—with 100% and the Tonight Show brand 15-17 rating points (45 share or so) are plausible for the first episode, even higher.
 
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This is way too much fun. More suggestions:

Say the 1988 Writers' Strike kills off both Rivers and Sajak, with Letterman the last man standing barely a year into his Tonight run.

The Late Show: FOX tries to soldier on with somebody else but the window is closed on Arsenio. It would be funny if they tried to poach Leno. Not that they'd succeed.

The Pat Sajak Show: More importantly, the benchwarmer for Sajak on the daytime Wheel isn't as disastrous as Rolf Benirschke was IOTL and the show's still on NBC in the spring of 1988, but conveniently he's only been signed to a one-year contract and Merv Griffin lures Sajak back when it runs out. The daytime Wheel is saved - and America gets to keep seeing Wheel twice a day through the 1990s. And 2000s. And 2010s. IOTL, The Price is Right was the sole survivor amongst daytime game shows. If Wheel of Fortune sticks around too, maybe it'll prop up others, or at least convince executives to maybe take a chance on making more of them.

Carson: Well, since you're standing up for his work ethic, I remind you that even IOTL he signed a continuing development deal with NBC, and even promised in his closing monologue on the last show that he'd be back in some capacity - but of course he never was. ITTL, he's five years younger, and NBC didn't wrong him by picking the wrong replacement, so maybe we'll see Carson Productions mounting more projects. Also, there's no reason for him not to be a real guest on Letterman's Tonight (weird OTL cameos notwithstanding) - Jack Paar appeared on Carson's Tonight, it's not like there was some tradition against it.

Also, if Carson signs a one-year renewal but is only intended to honour half of it, then for the remaining half-year or so we can fill the fifth day of the week with 2 1/2 hours of Best of Carson since we don't have "Best of Letterman" or "Best of Seinfeld" yet.

Letterman: The man idolizes Carson, so he won't want to beat his 25-year record hosting The Tonight Show. Which means he retires no later than 2011, after 24 years (and a combined 29, including his five years on Late Night).

And hate to put your feet to the fire, but you need to make the call about Shaffer. Would he follow Letterman anywhere?

Leno: He has two destinies. Either he pulls a Joan Rivers and lets himself get lured away by a rival network to host a competing show to Tonight, or he sticks around long enough for Seinfeld to retire from Late Night and then takes it over. The former option could happen as early as 1988, but as for the latter...

Late Night: Richards as the second banana works really well. I'd also posit that he is dressed in a very neat, clean-cut style (anachronistic - like OTL Kramer - but in a fancy suit instead of leisure clothes), the better for the physical comedy to "land". A rough sketch of the show's format:

Opening Monologue. Jerry supervises the writing of these. Humour is generally more observational and esoteric, in his typical style, than topical. "Letterman told all the funny Dan Quayle jokes already, Larry, I can't do them now!"

Opening Sketch: These are Larry David's babies, though Jerry and others help with the writing as necessary. (Richards generally contributes ad libs only.) Basically a Seinfeldian conversation/debate between Jerry and Michael. It reminds us readers of Seinfeld; given the antagonism of the characters it'll probably remind TTL viewers more of Archie and Meathead's more esoteric arguments from All in the Family (whether to put both socks on, then both shoes, or one shoe and sock and then another, what order to eat the food on your plate in, etc.). Four per week should add up to about the average episode of Seinfeld's worth. Every sketch ends with some pratfall by Richards (which will remind viewers of Chevy Chase's antics on early SNL).

First Celebrity Guest: More tightly written than other interview segments, given that this is the biggest name guest. Big "moments" from these segments tend to appear on entertainment newsmagazines the following evening. Think all the big Larry Sanders setpieces.

Mid-Show Sketch: More heavily improvised, usually building on earlier material in the Seinfeld tradition. As the show runs on, it gets more in-jokey and self-referential to earlier material, again like Seinfeld.

Second Celebrity Guest: Usually an NYC local (we are assuming this show is shooting in Letterman's old studio at 30 Rock, right?), probably mostly SNL performers, sketch/improv performers and Broadway actors at first, people who know David and get the "style" the show is trying to achieve and are able to improv and riff accordingly. Much looser than the first celebrity guest. Also a "swing" segment prone to bumping if any of the preceding go long (as often happens in such an improv-heavy show).

Third Celebrity Guest: A comedian once a week, at Seinfeld's insistence. Twice a week, musical guests. Once a week, an animal trainer or someone "goofy" for more comedy hijinks, or perhaps a human interest or newsmaker guest willing (or eager!) to play along. Of course, if there are animals, Richards always "hosts" the segment. Of all the segments, the one most likely to have Seinfeld and David "prank" the interviewee - asking leading questions they didn't agree to, etc. - since there are unlikely to be repercussions and many newsmakers are odious people anyway.

The set looks really fake, even by late night backdrop standards. Think the projections in Airplane!-level fake. Might as well have a dash of ZAZ-type absurdist humour in the show too.

David presumably tires of Late Night after several years. If we go with OTL Seinfeld, that would be seven, which brings us to 1994. As with Seinfeld, I suspect Jerry attempts to soldier on without him but quickly tires of it, maybe even crashes and burns, and the show only goes one more season (unlike Seinfeld's two) before he hangs his hat. Leno, assuming he hasn't deserted NBC, gets the Late Night hosting gig on the strength of his almost a decade guest-hosting Tonight (and all the time he's spent rubbing shoulders with the affiliates in the interim.)

Later: Costas only stuck around for six years IOTL. Do we assume that the better ratings enjoyed by NBC's lineup (and, perhaps, the lack of controversy) convinces him to stay on longer ITTL? Maybe he leaves when Seinfeld does, or pulls an OTL Letterman and bolts when he doesn't get Late Night? And when he does leave, NBC goes with a more serious choice of replacement than Greg Kinnear?

Ratings: Letterman had a narrative behind him IOTL that he won't ITTL. IOTL he was "wronged" and was seeking his vengeance. ITTL it's the Heir Apparent replacing Carson. He'll still get high ratings, I can't argue with your excellent analysis. But I don't think they'll be ionospheric; merely stratospheric. Which is more than good enough. So Carson gets a 7.0 or perhaps a bit higher in his farewell season (IIRC his ratings went up in his last season IOTL, how much of that was Arsenio's star waning vs. people tuning in to reminisce is another question). Say Letterman gets a 14.0 (his OTL 10.9 divided by 70%, and then with a 10% deduction to account for the lack of an epic narrative) for his debut episode. At least allow that Rivers and Sajak would depress his ratings slightly in season 1 (say he's averaging in the 8s or low 9s by the time of the writers' strike) only for a solid improvement (at or above your 9.5) by season 2 when even their sorry excuses for competition are gone. Double-digit ratings, even? And even better in the 18-49s.

Seinfeld I see doing phenomenally with 18-29s (Late Night is an obvious Generation X touchstone ITTL), and very well with 18-49s - with a higher ratio of viewers in the prime demo than even Letterman manages. Costas on the other hand skews older (definitely appealing to the Tomorrow audience... at least those of them who still stay up that late) but his share (as opposed to his rating) is probably amazing. He has to be pulling over a 50 share, surely. What else are people watching at 1:35 AM?
 
Sounds good. I can see Carson being the heir apparent to do the Bob Hope-type specials at Christmas; I forget when Bob Hope started slowing down, but perhaps part of his work is in doing those, with some in jokes at first from the Tonight lineup about how he's now gone to one show a year :) ALthough he'd probably actually do a few others, too - maybe host a Rose Parade here, a Memorial Day celebration there, especially during the Gulf War.

One famous moment I recall, for Carson in those 5 year OTL was Orel Hershiser's appearance where he asks him about what appeared to be singing in the dugout during the World Series, and he said he enjoyed singing hymns and sang the Doxology. Letterman's approach to that might be a bit different, though it still happens - he might turn it into jokes about God being on the Dodgers' side and givng them an unfair advantage, and then a few Top Ten lists will probably make reference to things like that. Or maaybe Letterman will crack that this is one other difference between baseball and football like the old-time comic's list - football has Hail marys, so of course baseball should have the Doxology.

I think Leno is happy with guest hosting till 1995 or so. He might be promised ten years on Late Night and then move up to Tonight with Letterman leaving after 2005 or so.This lets them keep him.

Interestingly, as I thought about it before, and especially after reading Brainbin's comments above, I was reminded of ESPN's The Dan LeBatard Show with Stugotz, which has a lot of the same type of stuff as Seinfeld in TTL - in jokes, talkjing about the making of such a show (and sports shows in general) itself on air, stuff that seems like absolute randomness, etc.. I wonder if Seinfeld TTL popularizes that type of show much earlier with his work on Late Night, to the point where it doesn't take 8-9 years of being aa local show before going to national in 2011 or so when it comes on from 4-7 - and then eventually replaces Colin Cowherd when he moves to Fox Sports. Pehraps LeBatars becomes a national show much earlier. I don't watch or listen to a lot of stuff nowadays, so I don't know, mabye such a show is more common than I think, but I definitely see the comparisons.
 
Ah crud. Ate my carefully planned comment because I wasn’t thinking lol. Alright we’re reduced to my memory, which is uh wonky.

@Brainbin
Even better is that the 1988 Writers Strike reduces NBC costs on Tonight Show to like zero with reruns/Letterman free-styling/guests. Perhaps Jay Leno monologue takes over the scripted parts of Seinfeld Late Night.

I love the take on a resurgent game show industry. Greater success in America leads to earlier cross-pollination with the UK?

Carson
I think Carson tells NBC he’s quitting via the 1986 Upfronts with zero warning just like he did in 1992 OTL. However in 1986 I think he is more careful to say he’ll be retiring in his 25th Anniversary year, rather than pick a date. That gives NBC just enough wiggle room to shower down the cash for those two months as a launch pad for Letterman/Seinfeld. So yeah, with 5 less years of cash I think Carson makes NBC pony up big via the retire in May 1987 threat. (Agreed on Best of Carson, quibble on unimportant details like length.)

Letterman
I honestly don’t know how long he’d last at NBC. Like if he doesn’t want to leave and he’s doing great in the ratings (yes, yes, I presented the optimistic take—I don’t even like Letterman much as a host, I’m a Ferguson guy, but at least he was talented when he tried coughLenocough) I cant see why he would leave—unless LA isn’t working for him, and NBC still like is not fond of him, Letterman is a terror, and everything adds up: Letterman pulls his version of the other great what if of Carson jumping to ABC 1981. Carson listened to Lew Wasserman because of course and didn’t, but Letterman might. (I just don’t know on Shaffer moving lol, that’s why I’ve ducked it.)

But probably Letterman is untouchable because of ratings. And he hates change. In which case yes, he retires the May sweeps style just before 25th Anniversary that Carson did IOTL and considered in both timelines.

Leno
Oooh. He goes for whoever let’s him tell jokes. Which could actually lead to a decent show in the right format, stripping out musical acts and other stuff and basically Leno monologue, guest, Leno and sidekick and sometimes guest riffing on news half hour thing. Syndication or maybe ABC after Nightline.

Late Night with Jerry Seinfeld
Much like Letterman did I suspect Seinfeld roams the halls of 30 Rock. I’d note that musical guests murder ratings. And this was also when Thursday Night movie advertising was uplifting NBC real hard. If Seinfeld wanted to include a movie trailer and guest—to make fun of it of course, but that’s some massive free advertising—on Thursday he could reduce music to one night a week on whatever his least watched day is and make everybody happy. Said movie guest could also often be say the most minor role in the film or when possible any comedian that landed a movie role.

Otherwise your producers credit is in order, that sounds like a fantastic show. A late night show I’d watch!

Later with Bob Costas
Well circa 1993 Conan O’Brien is looking for a performer gig, the only problem would be how does Lorne Michaels get his hands on Later? (NBC using him to find someone comedic after Costas?) I know, right? But Conan at 1:35 could be downright nuts. Obviously Dana Carvey is probably more likely to get the show, let alone a number of others. But it might be fun.

My alternate answer is Phil Hartman. Leno offered him the sidekick role on Tonight and NBC kept him on SNL by offering a weekly variety show IOTL. He’s only my alternate answer because:

Letterman/Seinfeld/Conan
One year, where the no Larry David season overlaps with first year of Conan?

Letterman/Hartman/Conan + McDonald
Where McDonald instead of Richter becomes the sidekick/host, and Hartman gets a bigger offer.

Ratings
Oh indeed, I ran an optimistic version. Totally fine with yours.

@DTF955Baseballfan
I like your Carson take—I could see him having retired earlier still needing that live audience joke rush—perhaps he goes cold turkey for a couple years and then comes back Bob Hope like.

Edit:

On thinking about it more, I think Conan works better for what Lorne wanted: showrunner. But he may wind up sidekick as well? To who?
 
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