David Letterman was not invited to Oprah’s “big gala” in Chicago on Tuesday night, and the late-night host, whose relationship with the queen of daytime television has never been hunky-dory, is so upset he feels like his head is going to explode. Or so he says.
On last night’s show, Letterman first honored Winfrey during his monologue, laying it on so thick in his typical flip style that you couldn’t tell if he meant a word of it. Take a look below.
Once he got behind the desk, he shifted gears, ranting about his snub in mock anger. “I spent the last 12 to 15 years kissing up to Oprah,” he fumed. “Honest to God. Every day, I get out of bed and I think, What can I do to suck up to Oprah?”
Paul Shaffer consoled Letterman by saying, “I don’t blame you for being upset,” but the host wasn’t finished. “More than upset. Crushed. Disappointed and crushed. I want to bask in the glory that is Oprah, who doesn’t? I say, who doesn’t? So I’m laboring with a broken heart here tonight.”
It’s interesting: Oprah is the one person who seems to flummox Letterman. I actually believe him when he once told Jon Stewart, “In the beginning, Oprah frightened me … because she could squash me like a bug. She could put me out of the business. And she hated me, that’s what it was.”
As a result, he constantly struggles with the right comic tone whenever her name is mentioned. He seems to be torn between wanting her to like him and resenting the fact that he has to make the effort in the first place, so that even the kindest words come out with traces of bitterness.
Did his “rant” seem playful to you, or was his insincerity indicative of their complicated relationship?