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.