David Letterman Says Jay Leno Is The Funniest, Most Insecure Person He’s Ever Known

01.03.13 24 Comments

Oprah Winfrey’s big honking interview with David Letterman airs this Sunday at 9PM on OWN (I wonder what that stands for. Oil Wrestling Nebraskans? Obscenely Wide Neckties? Octogenarians Watching Norbit? I guess we’ll never know), and to promote the special the network has released a teaser clip where Oprah asks Dave about his relationship with Tonight Show host Jay Leno. Apparently the two have some history. Who knew?

Anyway, I guess the big news here is that Letterman describes Leno as “an unusual fellow” who is both the funniest, smartest person he’s ever known, and also the most insecure person he’s ever known. I don’t know. I’m of two minds about the whole thing. On one hand, I am endlessly fascinated by Jay Leno. I just can’t, for the life of me, figure out what his deal is. Two separate times he weaseled his way around to more or less hose someone out of the Tonight Show gig, and for what? Almost all of his late-night colleagues despise him, he doesn’t appear to have any interest in doing anything with the show beyond running on stage and picking off all the low hanging fruit he can see, and he’s made it very clear that he doesn’t need the money. I really don’t get it. I want to, but I don’t.


On the other hand, I kind of wish Letterman and Conan O’Brien would just talk about, like, anything else for a while. I know this is an interview and it was an answer to a direct question — one that will understandably be asked anytime either of them sit down for something like this — but it’s starting to get a little of a “my buddy’s girlfriend dumped him months ago and he still won’t stop talking about it and it is bringing me down, man” vibe. Maybe that’s just because I write about television and it’s constantly on my radar, but I’m starting to hope the two of them just do a no-holds-barred, hour-long HBO special called One Last Time: About Jay where they sit in very comfortable chairs, get everything off their chest all at once, and then put it to bed.

Kimmel can moderate. I would watch.

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