
As much as I loathe Jay Leno — I think he’s basically the guy the characters in Idiocracy would look at and think, “We’re headed toward an Idiocracy — he’s had a particular hold on both David Letterman and Conan O’Brien. In fact, both of their careers are, to different extents, defined by Jay Leno. Leno weaseled his way onto “The Tonight Show” ahead of the rightful heir, David Letterman, and then he weaseled his way back on after he retired by ousting Conan O’Brien. Both Conan and Dave are clearly bitter about it, although I think Conan a little more: He’s fallen further, and I don’t think Conan can go five minutes without mentioning the ordeal. I think it’s fair to say, however, that both have had a hard time letting it go.
So, it was fitting that last night the two would finally get together — for the first time in 13 years — to commiserate about their shared disdain of Leno. It’s funny: The only time I’m really ever that interested in the late night shows anymore is when they’re talking about this stuff, but it is fascinating to me. Even though I don’t keep up with their shows as much as I once did — I was once religious about watching both “The Late Show” and “Late Night” — I’ll always have a fondness for both Dave and Conan, and here it feels like two greats telling war stories. It’s great TV.
Here’s where Conan talks about his relationship with Leno before “the debacle.”
Finally, here’s where Conan talks about his post-”Tonight Show” life, and Letterman talks about what a “brat” Jay Leno is.



ALERT ALERT!!!! OPEN QUOTATION!!!! WWWEEEEOOOOWWWWWEEEEEOOOO
War stories? Yeah…similar. OR two guys whining together because they got beat. I do find it funny when they do the Leno impression.
I guess that depends on how you define “got beat.” I mean, I guess you could say Leno won over Conan because he got the show back, but it’s not like he’s been a success since then.
Neither has Conan. Or Dave. Leno has beat both of them in ratings. Because while he may be a brat, Leno hides his smugness way better than Conan or Dave. Also, I think Dave and Conan’s comedy is too “smart” for the majority of the population. More so for Conan than Dave.
He doesn’t hide his smugness as well as he hides his funniness.
It does kind of sound like to women getting together to vent about a common ex-boyfriend. Dave’s the ex-wife, while Conan’s the fling.
I don’t understand how you get that Conan is more bitter than Letterman from that. He looked uncomfortable answering most of the questions and Letterman’s been holding a grudge for two decades…
I agree with this. Conan has always been very tactful and not one to talk about the subject aside from the, understandable, self-depreciating comments made about the ordeal from time to time. The only time I have ever seen him really sit down and candidly talk about the whole Tonight Show ordeal was when he did that one-on-one interview on Dateline (or whatever it was).
Yeah, I agree with this, too. Dave kind of used his whole ordeal as motivation while Conan seems like he’d rather not talk about it. Of course, you could say he didn’t need to go on Letterman at all, but he really did look uncomfortable answering the questions.
Dave’s such a sourpuss that there’s not telling what’s making him bitter.
Rightful heir? Is the Tonight Show the Iron Throne? It’s a job, and the network et al decided to bring in someone else. Get over it.
It’s hard to disagree with NBC’s decision to go with Jay over Dave when you look back and, honestly, it’s probably been better for us Dave fans since it drove him to make ten years worth of amazing shows on a different network.
The Tonight Show is a dying franchise. The only people who watch it are the Baby Boomers who still long for Carson.
The truth is, if Conan had kept that show, he would have sunk since he never really fit the Tonight Show mold. Instead, getting fired was a watershed moment for him, where his target audience, the younger, hipper crowd, rallied around Team Coco and pushed him into iconic status.
Same for Dave. Losing the Tonight Show was the best thing that happened to either of them.