If you’re wondering what the three weirdest celebrities ever to be on a phone call together on-air, the answer is Dave Letterman, Lindsay Lohan, and Oprah Winfrey.
I could never have predicted the twists and turns of fate that would bring that trio together, but there they were on national television, chatting away like a gang of middle schoolers planning for their next sleepover.
In an episode that will actually air tonight, Lindsay went on the show and was presumably talking about her docu-series with Oprah when suddenly she got fixated on the idea of calling her. Dave was pretending like there was anything he could do to stop it, but he lost control of the situation as soon as Lindsay stepped on set, so it was only a few seconds before she had the entire audience chanting ‘O-PRAH, O-PRAH, O-PRAH!’
So Dave gave up on trying to parent her, and just brought out the phone to make the call. Because he apparently just has Oprah’s number lying around. And you know what? SHE PICKED UP. I’d say that that’s the most shocking part of this whole thing, but I can’t. Because the real shocking thing is just how bad both Dave and LiLo are at prank phone calls.
As soon as Oprah picks up, Lindsay starts to crow out “HELLO OPRAH LOVE ME”, but Dave shushes her because he has a real knee-slapper in mind. He changes his voice and then — get this! — pretends to be Lindsay’s secretary! My gosh, what a goof. Except then Oprah goes and ruins everything by saying the most terrifying version of “Who is this.” that I’ve ever heard. It’s not even so much that her voice itself is scary, just that I’m pretty sure the iciness of her tone went all the way through the phone line and snapped Dave back to his normal self.
And then they get all chatty and schmoozey with each other and talk about LIndsay is coping (“Tell me how you think Lindsay is doing”?? Total middle school three-way call situation!) and blah blah blah, but HOW TERRIFYING WAS THAT. That might’ve been the first time anyone ever pranked Oprah, and probably also the last. I think she might’ve scared Dave Letterman into un-retiring.