Letterman Oprah Feud Explained: Why Oprah 'Hated' Dave

David Letterman told Jon Stewart Tuesday night that Oprah "hated" him "long before" his infamous Academy Awards monologue about her.

While it has been widely assumed that their mini-feud (since-settled) originated during his "Uma, Oprah" speech during the 1995 Oscars, Letterman said that it actually started while the two TV titans were vacationing in the same place and he made her pay for his lunch.

"This predates the Academy Awards. She hated me long before then," he said of Oprah. "She was with Steadman, I was with my then-girlfriend Regina. We were both at a restaurant having lunch on vacation. I said to Regina, 'Oh, this is hilarious, I'm gonna make Oprah buy us lunch.'"

When the waiter came over with the check, Letterman said he told him, "Oh, this woman right over there has been kind enough to take care of our check."

Letterman said he waved to Oprah as he and Regina left the restaurant.

"We got a free lunch and that's where it started," he said.

In 2005, Oprah appeared on "The Late Show" where she and Letterman buried the hatchet.

"Could you tell me please what has transpired?" Oprah asked Letterman. "I have never for a moment had a feud with you....I want you to know, it's really over, whatever you thought was happening."

Tuesday night, Dave said he is "still trepidatious around Oprah."

The two appeared, along with Jay Leno, in a Super Bowl commercial earlier this year. She also defended Letterman to Leno, telling Leno that a joke he made about Letterman's sex scandal was a low-blow.

Comments

[Leah Ahern]

04:48 PM on 10/17/2010

Dave's story sounds an awful lot like this one: http://www.snopes.com/embarrass/dupe/checkout.asp

[Belle Starr]

04:51 PM on 10/03/2010

Oprah is such a wuss. If Letterman had done that to me, I would have paid for his lunch and then the paybacks would begin!!!! muhahahahahahaha!!!!!

[elspaniard]

10:32 AM on 10/03/2010

Haha Letterman pulled a Lloyd on Oprah? Now that's comedy.

[blueballs]

09:11 PM on 10/02/2010

Sometimes, one's failings are better left in the past, like Letterman's Oscar hosting. If he wants to punish himself, go to bed without desert; don't dredge that awful thing up again.

[doctim11]

04:20 PM on 10/02/2010

Don't watch Dave anymore. He used to be funny, now it seems like he's just kinda mad all the time.

[Rainbow Sparkles]

03:28 AM on 10/03/2010

LOL, Dave is famous for being cranky. Especially back in the day. You must not have watched him very often.

[Craig 212]

12:46 PM on 10/03/2010

The cranky old man routine is what makes him hilarious.

[hgovernick]

01:53 PM on 10/02/2010

The feud is finally over.  At long last I can get some sleep now.

[Kenyatta J Yamel]

09:21 AM on 10/02/2010

she refused to have your baby. or wait, you refused to have her baby.after all, she is oprah she can do anything.

[PresidentRobertBooth]

07:40 PM on 10/01/2010

Dave, you da man.

[b1986]

06:29 PM on 10/01/2010

I doubt Oprah hates him, but if she did I could see why. He's a man who has more then 99.999% of people will ever have and he is still bitter.

[MorpheusXNYC]

02:35 PM on 10/01/2010

Wow... I gotta say, that dine and dash and leave Oprah holding the bag for his lunch - even as a practical joke was a pretty insanely douchey move on Dave's part.

Very sophomoric, college frat boy style antics on his part and I can totally understand why Oprah would want nothing to do with him.

Sure, misunderstandings happen, people say things they shouldn't and regret them later - all these things can be smoothed over with an explanation and sincere apology, but then some things are just so declasse, so gauche, so revealing of poor character that it makes you irredeemable in the eyes of some others.

Oprah showed real class and maturity by letting this roll off her shoulders.

[I3addog]

02:55 PM on 10/01/2010

Dude, he was on a date, he was trying to get him some, what better way to impress than getting the big O to buy you a meal ?

[twowrongs]

03:01 PM on 10/01/2010

Frat boy antics are Dave's bread and butter, but in general they are not mean-spirited. I bet he thought Oprah would get the joke. I bet she did. Eventually.

[cameron d]

02:29 AM on 10/01/2010

I found the story hilarious and completely plausable when told by David Letterman. Fantastic.

[toocoldout]

10:16 AM on 10/01/2010

It wasn't funny or plausible.

[cameron d]

11:42 AM on 10/01/2010

Well it seemed to make one Jon Stewart laugh pretty loudly. I wonder why it is that he and Colbert (two very funny people) go on Letterman's show almost annually but you never seem to see them on Leno?

I wonder why that is? Oh that's right. Letterman is a funny guy.

[Eric8869]

01:17 AM on 10/01/2010

this is still a lie - the reason she didn't like Dave was because years ago he broadcast his show from Chicago at the Chicago Theatre for a week. Oprah was his guest and this was before her show "took the high road". She had done a show on Satanic Sacrifices that day and he teased her about it. Pretty much made her look stupid and embarassed her about the topics on her show. It started then.

[toocoldout]

10:16 AM on 10/01/2010

She made him look stupid, by pointing out that that the subject was very serious for the people involved and not a laughing matter.

[corsair1917]

05:00 PM on 10/01/2010

Oh, did Oprah have Christine O'Donnell on her show too?

[LeftLeanWing]

11:13 PM on 10/02/2010

and her little dog too......

[srivers]

12:08 AM on 10/01/2010

One senses that the countdown to Letterman's 2012 retirement has already begun.

[newswatch]

06:22 PM on 09/30/2010

Dave Letterman is a "has been" dirty old man! He isn't even funny and, furthermore, he should leave politics out of his skits because--like so many on the left--he strikes discusting below the belt comments.

[KingHuff]

12:03 AM on 10/01/2010

" discusting" ? nice try at phonetics.

[HeavyHitter]

05:47 PM on 10/02/2010

Why is it that the right can't be funny? (And no, Dennis Miller is not funny.) They are so envious of Stewart and Colbert, they could scream. But they can't even approach that level of humor. I think it's because they are an unintelligent lot with no sense of irony or ability to enjoy self-parody.

[Rainbow Sparkles]

03:29 AM on 10/03/2010

I think they watch Leno. That explains A LOT.

[RyokoMocha]

04:39 PM on 09/30/2010

I can't stand Oprah Winfrey. David Letterman, though, is funny.

[LeftLeanWing]

11:14 PM on 10/02/2010

thanks for sharing