Name: Oprah Winfrey Got Stuck Paying For Dave's Lunch | David Letterman
Uploaded: 2024-08-20T15:02:01.000Z
Description: Watch the stand-up comedy video 'Oprah Winfrey Got Stuck Paying For Dave's Lunch | David Letterman' from Letterman on Comedy Buff. Published 2024-08-20. Transcript available.

Watch the stand-up comedy video 'Oprah Winfrey Got Stuck Paying For Dave's Lunch | David Letterman' from Letterman on Comedy Buff. Published 2024-08-20. Transcript available.

Oh, man!
Boy, you look good.
Well, thank you.
What exactly is this?
How would one describe this?
It looks like you're doing work on the highway.
I don't know.
Well, these are just some jeans.
These are cheap jeans, too.
Well, you look great.
Thank you, David.
Now, how long have you lived here in Chicago?
I've been here since, I think, 84.
I came here January 84.
Now, describe for us.
Now, you were like an empire in and of yourself now.
Do you think so?
Well, of course.
You're making, like, some people say, like, $40 million a year.
Low estimate.
A low estimate?
No, no, I'm kidding.
Only kidding.
No, I came here in 84, and when I did...
You came here from where?
Baltimore?
Baltimore.
And when I did, I remember when I first applied for a job here,
I remember thinking this was really one of the best cities in the world.
I really feel that way about this city.
Thank you.
I do.
And you know what's great about it?
So what you're saying essentially is screw Baltimore.
Well, no, because, you know, I sort of grew up there.
You grow on from one place to the other.
You know how it is.
Yeah, yeah.
But I came here and I thought, this is going to be my tariff.
Well, it just turned out to be here.
Yes, it is.
It's wonderful.
And what is your life like here?
What do you do for fun?
What do you do for recreation?
What do I do for fun?
I don't know.
I go to the same places everybody else goes to.
I mean, I have a restaurant here, and so I hang out there.
Tell me about the restaurant.
What kind of place is that?
Because let's run down the restaurants.
Mike Ditka has a restaurant.
Anybody been to Eccentric?
Thank you.
Yeah, I'm like this.
Harry Carey has a restaurant.
Yeah.
I'll bet that's fine dining.
I was actually there.
Really?
I was actually there.
I had a good time.
Jim McMahon had one.
I guess it's gone south.
That's what I heard.
You have one.
Everyone in Chicago has a...
No, but see, I really don't have one.
I have one with Rich Melman, who has 30 others.
And so I partnered up with somebody who knew what they were doing.
Rich Melman is like a, what, a gangster?
This is a mob guy or what?
No, he's like a major restaurateur.
Major.
You know, he has Ed DeBevick's, if you've been over there.
I've never been to Ed DeBevick's.
Oh, yeah.
So I'm not like one of those celebrities who says,
yeah, I think I'm going to go buy me a restaurant.
You have to team up with people who know what they're doing.
So you're just, to hell with the restaurant.
You're in it for the dough.
Actually, I'm in it for the fun.
When I started...
Now, what kind of place is it?
If I were to go there, what kind of place is it?
It's diverse.
Diverse.
I'd say it's diverse.
There are all kinds of interesting people.
I think it's probably the fairest representation of everybody in Chicago.
Now, what does that mean?
You don't think so?
I do.
I do.
I don't know what that means.
It means you see black people in there.
That's what it means.
Okay.
Yeah.
So...
That's what diverse means, eh?
Well, no.
No, but you all know how it is.
Because you can go to many restaurants in different parts of the city, and you
don't see a lot of...
When's the last time you saw a lot of black people in a restaurant?
Now, really, when's the last time?
It seems to me now, in New York, you see black people in restaurants all the
time.
I've been to restaurants in New York, and I'm always the only one in there.
It's the truth.
Let's talk about something else.
Yeah.
Well, anyway, congratulations to you, whatever your restaurant is.
Speaking of restaurants...
No, no, no, no, no.
No, no, no, no.
Tell me about your boyfriend.
Well, how did you meet him?
What's the deal on the guy, and...
Well, I met him, you know, I'd seen him around places, and I, you know, and I
thought he was
a nice guy, and...
But he was dating somebody, I was dating somebody, and so...
What does he do for a living?
He's a PR VP.
A PR VP?
Yeah.
A VP of PR.
Not in this city, though.
Where does he work?
North Carolina.
So I'm in the midst of a long-distance kind of relationship.
Is this like your first serious romantic liaison?
No.
No.
But is it more serious than others?
Mm-hmm.
Really?
Mm-hmm.
And his name is...
Steadman.
Steadman.
Great.
Well, I hope this works out.
He's the first person who noticed you when we were at that place.
He said to me, there's David Letterman, and I said, no, it's not.
It's a guy who looks a lot like David.
That's right.
See, people don't know what we're talking about, and we have to do a commercial.
Okay.
All right.
We'll be right back here with the lovely, the talented Oprah Winfrey.
This, I don't want to belabor this, but isn't this a very odd sensation?
Because when the lights come up, you see this first level of people, and you
think, oh, my God,
someone really important has died, and it's a huge funeral.
And then you look at this layer up there, and it's like twice the other people.
You know, at 20 bucks a pop, we're doing good business tonight.
All this for you.
Well, welcome.
I want to say welcome because I have never seen anything like this in Chicago
before.
Great fun.
Great fun.
It's really incredible.
You know, I watched, I got to see your program yesterday.
You did?
Satanic dismemberment.
Well.
Does, is that happening a lot now?
Well, see.
Now, I, I know, I know if it happens to someone, it's a bad thing and you feel
terrible about
it.
But does it, is it sweeping the nation?
Listen, listen, I, I really, I really, I just told you I'll talk about anything,
but I really
don't want to make light of it.
No, I don't, no, no, because, no, God forbid, somebody I know is dismembered
satanically.
I really do think it's a, I really do think it's a very serious thing.
Oh, very serious, but, but.
And I think it is happening, I think, as I said on the show yesterday, I know
you don't
want to get heavy here, but I think that all of Ripper Dave, thank you.
Oh, please.
Thank you.
I think that.
Suddenly it's the World Wrestling Federation and I'm Vince McMahon.
I just think, I just think that if it happens to your child or your sister or
your aunt,
it's very serious and it's not fair for us to make light of it.
And I think that a lot of these children are disappearing.
That's what's happened.
Well, I'm sorry to have brought it up, but it just seemed to me like, is it,
you know,
maybe it's happening more than I thought.
It is.
Okay.
Now.
What, uh, you want to talk about the little lunch episode, the vacation lunch?
If you do.
Sure, I'd be happy to.
You were, you were in a restaurant in a vacation resort.
Uh-huh.
And, uh, you, I wasn't sure it was you at first.
And then you, you waved and you weren't sure it was I.
Right.
Right.
And so I thought as a joke.
So you just stuck me with the bill anyway.
That's right.
That's right.
Thank you.
Well, I tell you, and I've said this before, I mean, I paid the bill because.
You were very gracious.
I thought it was my bill.
Right.
And so it was, it's fine with me.
Yeah.
It was, it was interesting because the people in the restaurant essentially
spoke French.
Right.
And they were just being ninnies about the whole thing because they, they, what
they thought was that I was just walking the check.
Uh-huh.
And I kept explaining to them over and over again that you were one of the
wealthiest women in the world.
And.
And I could pay for it.
And you would be, not only could you pay for it, you'd be happy to.
But then later as I'm leaving, I'm thinking to myself, because, you know, on
vacation people look differently.
Yeah.
And when you see them out of context, you're just not sure.
That's right.
I was thinking on my way home, I thought, geez, what if it wasn't Oprah?
And if it was some woman from Milwaukee on vacation, I just passed over my
check.
It really was, I don't know how it all got out because it really was no big
deal to me.
I just paid it.
And I.
Oh, this is good to know.
No, I just.
That's very good to know.
I just didn't, I just didn't understand how it got to be such a big deal.
Someone called me and said, is it true that Dave did this to you?
It was great fun and I enjoyed it.
It was the highlight of my vacation.
Boy, you know, you're, when was the last time I saw you?
Um, probably three years ago.
Last night.
Thank you.
You're welcome.
Thank you.
Uh, you're, you're terrific.
It's, it's great to have you here and I can't believe the success you've, uh,
achieved and
nobody deserves it more than you.
Thank you.
Nice to have you here.
Thank you.
This woman is, uh, Oprah Winfrey.
We'll be right back.
Thank you.
Thank you.