And yet, Jay Leno is still unfunny.
However, as you go on to note, these shows are very rarely about who's funniest. They're about being reliably pleasant. Jay, for all his flaws, ran the Tonight Show as something that was/is consistently watchable. His monologues are never offensive. He makes the guests comfortable. Late Night talk shows are really the TV version of comfort food and while Leno's stuff is a bit bland it's never upsetting or uncomfortable.
It's really difficult to accurately determine this situation, because it was so unique. Had NBC allowed Conan O'Brien to flourish, like they did Jay Leno, he might have found his groove and the ratings for his Tonight Show might have stabilized. The fact is, Jay Leno was doing pretty badly in primetime, and they never should have given him a primetime show.
Yeah. Conan had Jay's primetime show as a lead-in. Jay has hit NBC series.
Which falls back to Leno. When NBC basically told him they were planning on replacing Leno with Conan back in 2004, he probably should have just went quietly into the night, like he was planning on doing, and then not spring the complete opposite on NBC just as Conan was about to takeover. It wasn't fair to NBC, who scrambled and tried to appease all parties, and it definitely wasn't fair to Conan.
Listen. I much prefer Conan to Jay (or Dave). But this whole "Jay should have just quit" thing is a little unfair to him.
Jay was winning his time slot. He was not ready to retire. The network basically fired him to try something different. Then, when he made noise about doing what anyone who's fired would do (look for another job), the suits paid him to stay with the company. No one forced them to do that. That
was the first slap in the face Conan.
Then, when Jay's new show wasn't working and Conan's new show wasn't (in the minds of NBC at least working), NBC had a choice. They could have bought out Jay or they could have bought out Conan. They chose Jay. That
was slap two.
Jay did what most people would do when offered a job he wanted. He accepted it. And, let's face it, if Jay hadn't, there's no reason to assume NBC would have gone after Jimmy Fallon, Jon Stewart, Garry Shandling, or anyone else they thought would get higher ratings that Conan.
Really, the villain is isn't Jay. It's the idiot executive who set this up in the first place and then kept compounding the problem.