I went to a Letterman taping in 2011. Just before the taping, I bought a sandwich from Rupert. Nice guy, took a photo with us and everything! While there, I also bought a Late Show t-shirt. Then, while in the studio audience in the Ed Sullivan theatre, Dave noticed my shirt. He asked me where I got it, and I told him I got it at the deli. He made a self-deprecating joke à-la-Letterman about how their show is so bad they have to sell t-shirts out of a deli (hahaha)... then he asked me how much I paid for the shirt. I said “twenty bucks” and then he took $20 out of his pocket and gave it to me. Crowd went nuts. I will never forget that... my little Letterman moment!

Dave: do you know how we play Please stop calling me Chief? Rupert: yeah you just keep calling them Chief.

I absolutely MISS television like this. No one did it better than Dave in Late Night.

Ruperts face when they were going to disqualify him. 😂😂😂😂

Fun to explain to your kids : I used to set up our VCR to record Letterman when I had to go to sleep as a kid, then watched it the next day after school!

i love how dave sticks it to those greedy ass landlords at the pizza place. imagine seeing someone do that on corporate bootlicker TV in this day in age.

Dave was soooo good. Every night was an event. Even the the bad shows were good. I was lucky enough to be in the audience for a show in June of 2008. Jack Black was the main guest.

I liked it when Dave would send Rupert out with an earpiece and Dave would tell him what to say. HILARIOUS!

"Wow, audience making up their own joke." - brilliant

I love how you could be doing anything anywhere in the world and all of a sudden be on the Letterman show.

I once stopped by and talked with Rupert, he came out, we spoke for bout 20 min, he was a big OU fan & was interested in Oklahoma history, cool in person as on tv. Next time I was in NY, I gave him a SOONER ball cap. Rupert was so unassuming & perfect for Dave's sketches

This was my absolute, all-time favorite segment 🤣 It never seemed to kill, but Dave sure as hell loved it. That was the best part.

I remember when Dave had a daytime show. I loved him from the beginning and knew he was going places.

I had totally forgotten how funny the Rupert Gee stuff was all those years ago. Classic.....

Most laid back person on television. Rupert Gee

Rupert nailed this stuff. Kept it real down home.

Thanks for posting this, Chief.

His shirt means "Corn Dog Eternal"

Rupert is the best part of this whole bit.

Other late night hosts try to act crazy. Dave IS crazy. That’s the difference. 😉

7:57 Aww, man that was probably one of the best memories of this guys teenage years!

Wow. I didn't realize just how much I missed Dave. But then, I'm an old fart. Will it float ?

This dude used to be on all the time back in the day. I remember one time they just went in there to buy gum.

Dave's reaction to the song kills me

I miss these Rupert Gee skits. I wonder if he still works there. Might grab a T-shirt and a sandwich when I'm in town.

Stuff like this is why Dave was so great.

Yes Minnesota state fair on his shirt love it

FYI, the theme song is "Big Chief" by Professor Longhair. Get it, chief?

Hahahaha, just the first 25 seconds alone so clearly point out why Late Show with David Letterman was such a damn good show. Hahahahaha! It's just funny. It doesn't TRY so damn hard to be funny, it just IS funny.

Rupert's segments were almost always funny. He always just said stuff in such a dry way that it was funny, and they always had some situation or ironic gag going on also.

When Dave says, "Gonna have to disqualify you", Rupert looks STUNNED. I mean FUNNY!

Amanda thank you so much for posting such a treasure

I went into a bar and ordered a beer. Was sitting next to a guy and I said "what's up dude?" He looked at me kind of pissed and said "don't call me dude". I said, "okay dude". So, I'm laughing in my beer and just sensing the guy simmering next to me. Hilarious.

I remember my first time getting called Chief by a much taller and senior co-worker… I kinda had the look of Michael Scott getting awarded a “Dundee.”

This was when Late Night television was awesome!

I miss when you turned on the tv for some entertainment.

It's actually a good looking sandwich.

Good old times. I still remember it.

thanks for posting

I cringe that this was taped just slightly over two months before 9/11, and no one knew what was about to happen. Nick :-)

I miss you 90's. I will never, ever forget you.

Dave at his best. There will never be another one of him. Kimmel tries but he fails. Miss ya Dave.

Damn. I cant believe i didnt watch Norm McDonald or Dave Letterman until they were both gone. Fucking legends.

2:50 classic Dave I love when he would do something random like that

Surprised that after finding out Mike's parents were in the studio enjoying the show,Dave didn't go on a rant "Enjoying the show in air conditioned comfort while leaving your minor child alone on the hot dangerous NYC streets,hmmm folks"

Man O man, how we miss Dave every night..!

Oh nice I was in 9th grade when this aired. I also don’t think I would have figured it out lol.

Rupert is a legend!

rupert was always a good sport lol. letterman was the best. i remember one show he kept talking about how a lightning bolt shot through the studio and almost killed him. yet it never happened. just randomly through the entire show he kept mentioning this lightning bolt that wasnt real hahahah.

So happy and carefree. Little did they know what was coming in about 2 and 1/2 months

Since David Letterman show is no more, i miss the hello deli place.😔

Rupert made that sandwich in 60 seconds!

I miss this era of the show.

Dave made the simplest, everyday occurrence funny.

NowFallon has puppy quiz. Jeez

Pairing him up with jack hannah is awesome. I was lmao

im from uk and i went in that deli and bought the hello deli tshirt when i was in ny. i met the owner.

Somebody needs to upload “Please Stop Calling Me Debbie” as well.

Stop calling me Chief and Catherine Zeta Jones wow what a show

The one thing that would've made it funnier is if Dave told the kid the sandwich he just got "is valued at $500,000. You got one more sandwich coming Chief!"

Looking at the banner of Hello Deli in the video from 2001 ( 1:27 ) and then at Google Maps today. It's the exact same banner, complete with patch job in the upper right. That thing has stayed together for over 20 years.

Letterman and Conan were the best

Hello Deli just celebrated their 30th anniversary of being in business. There was a little ceremony outside the deli. Paul Shaffer was there & made a speech. Rupert was also there, of course!

Did they ever release a home version of _Please, Stop Calling Me Chief?_ If not, they should have.

👍thanks Amanda.

4:39 Wow, Tom Brady was only 15 here.

One million dollars .... worth of hello deli gift certificates! lol

An innocent day. 10 weeks later, the world would change forever.

5:49 the face 😂

Late night TV blows right now. Dave was the best.

Place looks pretty much the same as when I visited in 2018. :)

I just got my 6 year old daughter to say please stop calling me chief, then I showed her this video after I stopped laughing.

Miss nice kids like this. We'll mannered, confident, not glued to cell phone

1. Letterman, 2. Conan. No one else even compares.

stop calling me chief tune is "professor longhair's big chief" a NOLA classic

Is there an an episode of Please Stop Calling me Chief with a native american?

Does anybody know the title of the music played when they handed the big cheque?

Does anyone know the name of the song they started playing when the girls presented the check to the kid???? Is it Michael Bolton, A love so beautiful??

Spent a week in New York when it was cheap after 9/11 and the best part was going to the Hello Deli.

Even after years at CBS, this still had the genuine, off the rails, could go somewhere nuts feeling to it. Not as much as what I've seen from the old NBC Dave, but more than anything made now. It's all too manufactured and refined. The hilarity is always in the awkwardness and the errors.

Johnny left some pretty big boots to fill and boy did letterman rocked those puppies like nobody’s business. Anyone on air now isn’t even in the right department ....

Were there any other times where Dave played “Please Stop Calling Me Chief?” My boys and I have fun calling each other Chief as a result of this bit.

2018 update. Please stop calling me "Boss."

How is Rupert? Is he still there? Anyone know if he was on ant of Dave’s last shows?

That would be funny if he kept that gift certificate for 30 years and auctioned it off for more than a million. Ha!

I'm surprised his corn dog didn't bust through that check 🐣

Where csn I get that soundtrack!!!!!!!! "STOP CAAAALIN ME CHIIEF da da da."

I need more thumbs! Dave, Rupert and a sandwich - there's your deli combo.

We saw Rupert at his hello deli when we were in New York would have ask for a selfie i chicken out 😕

Rupert G, so many memories

Anyone know the song that plays when they bring out the giant gift certificate?

I worked with a guy that called everyone "slick" it was annoying, figured he saw his mother and called her slick

What's the song at 7:17 ?

The tall girl on the left was eyeballin that kids sammich...

Do you have the "She's already gone,Chief"clip?

Come on, Rupert. The shirt clearly says Corn Dog Uterus.

This is it chief

😂😂😂 Dave was the best!

That guy is my age…miss Letterman.

I met Rupert out on the street in front of the deli, had a brain fart and forgot his name, just looked at me like I was wetodded