The problem with discussing Jay and Conan's shows, as well as the rest of the late night debacle, is that invariably the author inserts his taste, which of course comes across as fact--that obviously Conan is so much funnier than Jay, that Jay is flat-out dry and unfunny. As much as we all do this to some degree, it's particularly irksome in this case, because both men--as well as the rest of the late night group (save for Carson Daly, but no one cares about him anyway)--are all established comics in one way or another. Sure, their humor, style and approach all differ, but that doesn't necessarily make one inherently unfunnier than the other. Jay had a loyal audience and was regularly beating Letterman by 20%--and ratings do indicate that he was popular. Someone was watching him; it may not be those who write the articles and Twitter obsessively, but he had plenty of lower-profile fans.
However, despite the partisanship, this Daily Beast article dissects why Conan's Tonight Show wasn't doing well, and he throws out the timeslot as hogwash:
The problems were fundamental. First is that here in the hangover of the 2008 election, we want political satire. O’Brien doesn’t do much political satire. If you think of the transcendent bits that surfaced on YouTube since Conan began Tonight last June, they’ve come from Jon Stewart and Stephen Colbert, various cable chat shows, even ancient Saturday Night Live.
Conan’s only major contribution to political goofery is Smigel’s (inspired) ventriloquism of politicians like George W. Bush. It’s no wonder that O’Brien’s Late Night ratings plummeted by nearly 700,000 viewers (more than 25 percent) back in 2008, when the nation glued its eyes to the campaign. It should have been an omen: His Tonight Show felt off-topic before it started.
That might not have been so deadly if the Tonight throne hadn’t distorted what made O’Brien funny. The problem is not the old saw that O’Brien’s “brand of comedy” doesn’t play at 11:35 p.m. Carson and Letterman had plenty of inspired wackiness, and Grandma and Grandpa liked them just fine. The problem is that O’Brien is really at his best as a straight man—the guy doing the horrified reaction shot when the masturbating bear runs out on stage. He’s a ringmaster rather than an emotional center of gravity.
This flows from O’Brien’s Harvard Lampoon sensibility, a kind of comedy that is impish and intellectual rather than crusading and heartfelt. (You can never imagine Conan snarling like Jon Stewart.) There’s nothing wrong with this, and it could work within the right show. But when O’Brien sat down at Johnny’s desk, the gravitas seemed to throw off his balance.
He goes on to say that the Tonight Show hadn't figured itself out yet. Well, duh. That's not a huge sin for a show that's only been on a few months, and talk shows--which tend to have hundreds of episodes over a multi-year run--should have even more leeway than other types of programs. They're done on the fly, working simultaneously on several days' worth of episodes. Anyone who's ever watched the same host multiple days in a row knows that they repeat jokes; that is, they exhaust the same stories, news items, and themes day after day. This week every host has been riffing on the Jay/Conan/NBC mess; it hasn't gotten old yet, but the jokes about Harry Reid have. It's the nature of the game, not meant to be watched night after night, but to flip casually among many. As such, some nights are bad; it depends on the jokes, the news, the guests, and if you stick around, you do get glimpses of the style. But each man and his respective staffs put on a show, and the effort is seen. Denigrating either performer for comedic chops is unfair to the work they do.