David Letterman admits to Jon Stewart that Oprah had a good reason to hate him

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I apologize in advance for the somewhat crappy video below – I couldn’t find any clips of Jon Stewart’s appearance on Letterman last night on YouTube. Anyway, I always love when Letterman and Stewart are together. Jon so clearly admires Letterman professionally, and I think Dave gets a kick out of Jon. Just my personal opinion? Jon is cooler and more awesome than Dave. I can’t help it – no one cracks me up like Jon, and it helps that he’s a really nice guy too. Anyway, during the show Jon and Dave started talking about Jon’s recent (awesome) appearance on Oprah, and that lead to a discussion about Dave’s history with Oprah. It was really funny:

Talk show host David Letterman had a legendary 16-year-long feud with his rival, Oprah Winfrey. But what was the cause of their mutual animosity? Most people think it was started when Dave hosted the Academy Awards in 1995. He kicked off show by making a really awkward (and unfunny) joke, where he pretended to introduce Oprah to Uma Thurman.

The “joke” was that he repeated their odd names again and again: “Uma … Oprah! Oprah … Uma!” he said, continuing the leaden gag for what seemed like an eternity. Every since then, people have assumed that this is why Dave and Oprah disliked each other. But on ‘Late Show’ (weeknights, 11:35PM on CBS), Dave revealed the actual reason — he stole a free lunch from Ms. Winfrey!

Letterman related the tale to guest Jon Stewart. “She hated me,” he told Jon. He then discussed an incident that took place “long before” the infamous Oscars failure.

Apparently, Oprah and her boyfriend were at an expensive French restaurant when Dave and his then-girlfriend Regina showed up. David then came up with a “clever” idea.

“This is hilarious,” he said to his girlfriend. “I’m gonna make Oprah buy us lunch.” Oh, man! Don’t mess with the queen of showbiz like that! But the impressive part is that Letterman actually managed to pull it off. He simply told the water that the “lady” at the next table had agreed to pay for his meal. Then, upon leaving the restaurant, he waved cheerfully at Ms. Winfrey — sealing the deal (at least in the waiter’s eyes) that the two of them had an arrangement. Thus was lunch stolen from one of the most powerful women in America.

But was some free French food worth starting a feud spanning nearly two decades? Jon Stewart didn’t think so. “Oh, for f#ck’s sake,” he said, after hearing about the prank. … On the other hand, Oprah is worth at least $1.5 billion, so she can definitely handle picking up the tab from time to time. However, Dave also has a fair amount of money himself.

[From TV Squad]

Yeah… do you really think Oprah was pissed about Dave’s dine-and-dash? Perhaps. I really do think that she just didn’t give a crap about David in general and she was just being a good sport when she finally gave into Letterman’s nightly pleas.

In addition to Oprah, Jon and Dave also discussed Glenn Beck too (video courtesy of Mediaite):

Love the comparison of Beck to a comic. Excellent.

Sept. 27, 2010 - New York, New York, U.S. - Comedian and host of 'The Daily Show' JON STEWART promotes his new book 'Earth (The Book) A Visitor's Guide to the Human Race' held at Barnes and Noble Union Square. © Red Carpet Pictures

Sept. 27, 2010 - New York, New York, U.S. - Comedian and host of 'The Daily Show' JON STEWART promotes his new book 'Earth (The Book) A Visitor's Guide to the Human Race' held at Barnes and Noble Union Square. © Red Carpet Pictures

Sept. 27, 2010 - New York, New York, U.S. - Comedian and host of 'The Daily Show' JON STEWART promotes his new book 'Earth (The Book) A Visitor's Guide to the Human Race' held at Barnes and Noble Union Square. © Red Carpet Pictures

Jon outside of the Ed Sullivan Theater on Sept. 28, 2010. Credit: WENN.

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23 Responses to “David Letterman admits to Jon Stewart that Oprah had a good reason to hate him”

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  1. ams511 says:

    lol loves it

  2. MeMyself says:

    Ohhhh..what could it be?

  3. mln says:

    He has told that story before. I think everyone forgets how much Letterman has softened since he left NBC he used to pull the meanest pranks on people so yeah I think that is part of the reason they had a feud along with all the fat jokes he used to crack on her.

  4. Hollowdoll says:

    Jon Stewart is awesome!!! great clip.

  5. Annie says:

    It makes sense, but I agree, it was the years of merciless fat jokes. Can’t say I blame her.

  6. Sandy says:

    JOHN STEWART FOR HOT GUY FRIDAY!!
    (Letterman not so much)

  7. Anti-icon says:

    Oh this is juicy! Yes, I do think this is the “joke” that really packed a punch for Oprah, but not for the reasons that you say. In Oprah’s eyes, David was a mentor, someone she respected as a professional in television. In Dave’s mind, Oprah is HIS mentor, and a prank like this will make her laugh, not insult her, or make her think she’s making fun of him. Large misunderstanding based upon the POWER/Perception.

    John is way too saavy and intuitive to ever misunderstand how much people need to be liked/respected, wherever they lie on the ladder of success.

  8. a says:

    i remember stewart as an MTV VJ!

  9. danielle says:

    That Oprah – Uma thing was one of the stupidest “jokes” I’ve ever seen. He was SO not a funny host.

  10. TaylorB says:

    Sort of off topic, but Jon was in it and I know I am showing my inner nerd here, but I just watched a great documentary about crossword puzzles and puzzle masters called Wordplay. Facinating movie! Jon is one smart cookie, and seeing him in this made me like him even more… a fellow puzzle geek.

  11. JM says:

    Please Kaiser, include Jon Stewart in Hot Guy Friday lineup. His impression of Glen Beck a few months back was spot on & hilarious!

  12. jc126 says:

    I think it was really that he used to make fat jokes about her all the time on his show, especially, if memory serves, joking about her eating a lot of ham. I also remember Oprah saying that when she was in the audience at the Oscars, she was terrified that Dave was going to mock her weight, and she also realized that she was the largest woman in the auditorium, which made her even more self-conscious.
    Still love Dave L.

  13. missmilly says:

    I can’t stand either of these pigs.

  14. bakerdoz says:

    considering that’s a scene from ‘dumb & dumber’ i’m pretty sure that’s not the real story…

  15. Maddie says:

    So what would have happened if the waiter was fired from this job, did Letterman even think of that for heavens sake.

    We all know how flaky some stars are, what if O pulled do you know who I am? or the manager could have done on his own (firing the waiter to cover any embarrassment of part of the restaurant.

  16. xxodettexx says:

    i looooooove jon stewart, crappy movies and all! 🙂

  17. Molly says:

    I remember Dave saying in one of his shows years and years ago that Oprah hated him because he was always making fat jokes about her on his show in the 80’s and 90’s when she was very heavy. To me, that seems like the real reason behind her (understandable) dislike of Letterman.

  18. Jeri says:

    Dave & Jon are my favorite hosts. They both rock!

  19. TaylorB says:

    Just curious, which two are the ‘pigs’? Jon, Letterman, or Oprah? And while you may not like their comedy what exactly (setting aside Davids sex life and Oprahs weight fluctuations) makes them ‘pigs’? Or is your comment based only on the fact you disagree with them politically?

  20. tango says:

    All 3 (Stewart, Letterman & Oprah) can just go away now.

  21. lu says:

    @TaylorB
    Maybe he is Glenn Beck

  22. TaylorB says:

    Tango… ssshhhhhh!! People who bash the ‘O’ tend to end up in cement sneakers. 😉

  23. Jello says:

    I want to be Jon Stewart’s second wife.