Jon Stewart Talks Oprah, Beck and O’Reilly on Letterman

by | September 29, 2010 at 10:48 AM | Late Night, TV News

It’s always an interesting treat whenever one late night host is a guest on another’s show. Last night, Jon Stewart of ‘The Daily Show’ was a guest on ‘The Late Show with David Letterman,’ and the two had a very cordial chat about everything from Glenn Beck’s potential pro wrestling roots to Dave relating the now legendary story of why he believes Oprah Winfrey hated him for years.

Letterman offered his theory on Bill O’Reilly, with whom Stewart has recently had a couple of verbal bouts, saying that O’Reilly doesn’t really believe what he’s saying, but Stewart didn’t quite buy that. “I think he’s a fair-minded individual who has his own bellicosity about certain issues,” he countered, before repeating what he said to O’Reilly the night before on ‘TDS’ about his relationship to Fox News – that “he’s the thinnest kid at fat camp.”

Watch clips from ‘The Late Show with David Letterman.’

Dave also figured out his theory on Beck, likening him to legendary pro wrestling manager Bobby “The Brain” Heenan in that “he’s just looking to make trouble. He has no idea what he’s talking about, he just wants trouble.” Stewart, who has made tremendous hay out of mocking and impersonating Beck, replied “I like listening to him. I think he’s an excellent broadcaster. He’s fun to watch because he does that thing, it’s a stand-up comedian’s trick. You know how when we used to be on the road, you’d do the same act night after night, so you’ve got to make it seem like it just came to you,” before launching into his fumbling impression of him.

Stewart also referenced the fact that Beck once played the classic Mean Joe Greene Coca-Cola commercial and wept about “why can’t we go back there?” Stewart’s response: “I think we can’t go back there because it’s fictional. I think it’s a fictional commercial. And then I remembered, I think they taped it in 1979, which is when the Iranian hostage crisis was. So I guess we could go back there, but why would we want to?”

Watch full episodes of ‘The Daily Show with Jon Stewart.’

The conversation later steered towards Stewart’s appearance on ‘Oprah,’ which led to a discussion of her incredible reputation. “I feel like the expectation, when you’re Oprah, is that when you meet her, she will help you. Even if you don’t really need help, you think ‘well, Oprah’s here, I must be getting something nice,” Stewart said. Dave agreed, quipping that “she’s made it difficult for guys like me because when these people come to this show, the only thing they go home with is a bad taste in their mouth.”

Dave then noted that Oprah used to frighten him 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.” Stewart thought he was talking about the Oprah/Uma disaster when Dave hosted the Oscars back in 1995, but Letterman assured him that “she hated me long before then.” As the story goes, both Dave and Oprah and their respective significant others were on vacation at the same island, and when they were in the same restaurant, he got an unfortunate comedy idea: “This is hilarious. I’m going to make Oprah buy us lunch.” He proceeded to trick the waiter into thinking that Oprah had offered to pay for their check, and then did the dine-and-dash, waving to her as they left to sell the joke. “That’s when it started,” he concluded, “And that, my friend, is why I’m not going to Australia.”