Glad to see Rupert again! Hope he’s doing well! Miss the show and Dave tremendously!

Rupert was always my favorite. His facial expressions were perfect for Dave's comedy

Rupert was fearless and always up for anything the show wanted him to do.

The roar of the audience as he leaves after delivering the slurpees... you have a lot of fans Rupert!

I had the pleasure of meeting Rupert twice, and each time he was the real deal, he would really just sit there and chat with you while he rung up your order. I remember going in one day with a network hub under my arm that installing later that day, and he actually knew about computer networking a bit and we talked about it lol. This had to be like 1995.

There needs to be a part 2 and 3 of Rupert's favorite moments (maybe more). I have SO many memories of him on the show. He was an absolute delight. It's great to see him again!

We love Rupert! So many great moments over the years.

The chick who stood up, "you touch me, you're dead", i think she was an assassin too! Great work, Rupert, you are The Dude!👍🏽

Rupert mic-ed up following Dave's commands was always great. The thumb in the water when he was working the restaurant patio is still funny.

Went to NYC for a week and did lots of cool things, but buying a couple shirts from Rupert was one of the coolest.

Rupert! I had the pleasure of dining at the Hello Deli in 2007 and Mr. Jee could not have been nicer. Still brings a smile to my face.

what a legend. I grew up with this show, this guy was pretty integral I always thought. lovely man

Man I loved Rupert's skits so much as a kid. So when my parents visited New York in the early 90's (from the UK) I pestered them to go get a photo of them with him. They had no clue who he was or why I wanted the photo. Still have it today and the awkwardness it contains is Kodak Gold!

This video made me miss the show more than most.

what a lovely human. Nice to see you Rupert!

Thank you Rupert! This series is one of the best things the internet has ever produced, and would be nothing without all the crucial characters like yourself. Thanks for bringing smiles and laughs to people the world over!

Thank you Rupert!! My biggest thrill was hearing you call out my order at the Hello Deli, “BIG-ASS, WHO HAS A BIG-ASS?!” 🤓❤️ The Big-Ass Sandwich was excellent!

Dave's Christmas tree trimming and trying to knock off the meatball was as much a holiday tradition in our family than any other festivities.

Clip not available. 😂 I laughed SO HARD at that.

Rupert! I'd totally forgotten about him - what a great show Dave gave us all those years...

Visited NYC a couple years ago and stopped in the Hello Deli just to check it out as a big Letterman fan. Walked in on a quiet morning and there stood Rupert! Didn’t really want to bother him with tourist nonsense so ordered some food and told him I was a fan of his time on the Late Show. He was super friendly and the food was great!

"It was my thumb." That woman was justifiably p.o.'d, but that segment was gold.

Rupert as a waiter had to be one of the best clips/shows of the 20th century. When I went to a taping back in the 90s, I did stop off at the Hello Deli and get a sandwich. I bumped into Bif there as well.

We love you Rupert. NYC for life.

Seeing all this warms my heart.😍

Hello Deli is on top of my list of NYC places to visit.

this is the "Favorite Moments" we were all waiting for.

My Mom and I went to see Dave in 1996. I was 15 ;) We got to go to meet Rupert as well. It was our first time to NYC, and I'm from Buffalo. Also was our first time on an airplane and on the return a train. Or vice versa. I love Dave. Probably seen most of his shows on TV since I was at least 10 years old until his retirement from the show. Rupert was super cool. Got a photo of him and me somewhere. He is very cool.

Rupert was always great! I miss the Late Show with David Letterman so much!

Rupert is my favorite ever skit/skits. I would like to see the follow up interview of the two ladies at lunch

As a kid I always loved Rupert on the show. Seeing him interview Jason Ferguson is even better. I had Jason's Mom as a teacher growing up. One year he bought her the nicest Tahoe you could imagine. Great people. Thanks for the trip down memory lane.

Thank you for playing along Mr. Jee Happy Holidays

Mexican drug cartel story is crazy! I miss everything about the show. Good times.

My life is complete. I've now heard Rupert Jee say "... and we start sucking face."

Rupert as a waiter tormenting the lady customers was one of the funniest things I ever saw.

All these years I thought it was "Rupert G.". The G abbreviating some difficult name to pronounce. 😂🙏🏼🤗

Rupert Gee is a national treasure.

I loved whenever Rupert was on.

Rupert the man, the myth, the gosh darn legend!

Thanks for all the fun times Rupert! Happy healthy retirement😘

When Dave began to visit Ruert, what a boom to business. The best advertising anyone could ever have.

Pure joy watching this clip (over and over). Thank you Donz; thank you, Walter, thank you, Dave. (Forever, thank you Mary.)

This guy was up for ANYTHING. What a gem of a person to have next door 👍

Rupert is amazing. I was always so afraid for his safety on those remote segments. Business owner, actor, comedian!

10:49 😂😂😂 CLASSIC!!!! My favorite Rupert moment 😂😂😂 COMEDY GOLD!! 12:02 with the water 😂😂😂 then he comes back with the glove Omg when I first saw this I was on FB floor laughing 😂😂😂 Love Rupert! We went to see the Late Show back in 2004. Jamie Foxx was there promoting Ray We went to have lunch at the hello deli , Rupert was sooo nice

When I visited New York in 2008, I wasn't old enough to go to a Letterman taping, so I did the next best thing and bought a candy bar (a Snickers?) and a bottle of water from Rupert Jee next door. When they tell you New York is the most exciting city in the world, that's why!!!

This is so so good. I understand why Rupert selected these, I love the "clip not available"

I had such a great belly laugh with these clips..Thanks for the blessing

Legend

Rupert Fun Facts: Rupert appeared on the Late Show 401 times, more than any other non-staffer (or staffer, for that matter, besides Paul). One of the Fun with Rupert segments had Dave and Rupert trading places. Someone faxed me a note claiming that there’s a complete compilation of the FwR remotes. I don’t buy it. Lastly, Rupert was (and maybe still is, I don’t know; he blocked me from entering the Deli after I five-finger-discounted some cash from his register some years ago. There are purportedly photos) a great guy. Despite his love for Englebert.

Oh I am so glad to see Rupert again! Thanks for this wonderful video.

Eggs and bread crumbs! Of course! THAT'S how you bind the meat!

I’ve never seen Cats before or do I remember Ruper singing in the musical 😊

The "bit" with Rupert serving the young ladies with his Thumb in the drink was CLASSIC!! ... and THEN with the Rubber Glove!! 🤣

Rupert!!!!! ❤️ I always enjoyed watching him on the show. This video made me laugh 😀 More great memories with Rupert and Dave, please! ❤️

Rupert Jee was a great addition to the show when you'd have him on. Merry Christmas to Rupert Jee & family 💛🎄☃️❄️🎂🧁🍨🍦🍧

"That'sa Spicy Meata Ball !" Hahaha Great clip. Thanks D.L. Merry Christmas All

met Rupert when i visited NY... super nice guy... bought my Letterman shirt and mug from him after seeing the show 🙂

I enjoyed seeing this Rupert update and reminisce

So great to see Rupert! His delivery of “It was my thumb” is perfect.

Love Rupert G, Missss you Rupert!

I went to Rupert Jee's back in the early 2000's. The food was so good that we went back the next 2 days. He was super nice and took pictures. I got the Paul Shaffer and the Regis Philban

Awesome to see Rupert again!

And LATE NITE TV has never been the same . Thx D A V E 😁👍🏻👍🏻

Been waiting for this one. Rupert was always my favorite on the show

Thus far, Rupert Jee is the king of "Favorite 'Late Show' Moments"!

Loved this. Thanks Rupert! And man, Jay Thomas can really spin a ball. RIP.

That wasn't just Willie Nelson. That was Kris Kristofferson on the right. This was awesome. Engelbert was fantastic. So was Rupert.

Merry Christmas Rupert! You are such a delight!

Love this! 😂

Miss the whole show. All good things come to an end sadly.

Hi Rupert!!! awesome memories!! wow on the El Chappo story! wow!!

I saw Rupert in the deli when I was visiting NYC in March. I was too shy to say anything to him. Wish I had, he brought me a lot of joy on Letterman.

I miss the show so much

Rupert! I went to a taping ages ago and had to answer a trivia question involving Rupert to get the tickets.

What a legend. I still hope I'll be able to get to NY one day and visit the Hello Deli.

The waiter bit is probably my favorite Dave segment

Rupert! Your segments were the best! I had a 24 hour business trip to NYC a few years ago and made sure to drop by your fine establishment! I came all the way from Utah.

The segments where Rupert followed Dave’s instructions left me unable to breathe. He might have been afraid of heights but he wasn’t afraid of much else. The Hello Deli is first on my list when I get to NYC, I literally don’t have an important second location to visit; maybe Times Square.

Merry Christmas Rupert, always loved you on the show!

I grew up throughout all of the 80’s and 90’s and was a big Dave fan. So much so that I had a cake at my high school graduation open house with a caricature of Dave with my own top 10 list on it. I also went to college for television and film production. But I grew up in the Midwest, and didn’t first get to NYC for even the first time until late 2004. NYC has so much to do, that it took me until my 4th visit just last year to get tickets for the Ed Sullivan Theater. Which was with Stephen Colbert by that time. Who I do love a lot too. But I stopped by the Hello Deli beforehand when I did. Rupert was there, and my girlfriend and I got some sandwiches and talked briefly with him. It was surreal. I know he’s not a celebrity like Tom Hanks or Julia Roberts, but for someone like me who grew up watching all of Dave’s bits with him, it was pretty darn cool.

AH HA HA..! Other than the interesting but kinda unsettling hit man story, I laughed all the way through this. I was looking forward to hearing Rupert's take. If I'm not mistaken, the reason they stopped Fun With Rupert was because some guy was getting ready to stick him with a shiv. Miss and appreciate you, bro. Will definitely make a special trip to Hello Deli if I'm ever in NYC.

I've got one of Rupert's shirts. Autographed. I have never set foot in New York.

I remember those women and Rupert saying "It's not my finger it's my thumb" like it was yesterday. I couldn't wait for those bits. Cheers.

What a great guy. Always enjoyed his segments.

Glad to see that Ruppert is still going strong after all these years. It's real a shame that he's had no involvement with Stephen Colbert after he took over The Late Show too.

One of the things I've always lamented about LSSC is that they don't incorporate the area into the show the way LSwDL did. Not that it should be expected, but by comparison LSSC might as well be shot in Moab, Utah.

Those where my high school years, adore Rupert ❤

Rupert is sweeter then saccharine and very much missed. (I'm often hipoglycemic).

RIP Jay Thomas

I didn't know it was called Fun With Rupert, I just remembered it as one of the funniest things I ever saw

"Who are you, the queen of England?"

The first time I got to NYC, eating at the Hello Deli was a nonnegotiable. What a thrill to meet Rupert-he talks about meeting celebrities-Rupert, dude, you ARE a celebrity!

Always enjoyed Rupert. Thanks Dave!

Rupert! ❤️

Needed a good laugh today, and this video did it! Forgot how funny these segments with Rupert were. Thanks for posting this! 😊❤️

Thank you for the memories Chairman Mao

We need a Staff Members Almost Getting Killed compilation.

For some reason I didn't think Hello Deli was still around. Next time I'm in NYC, I'll be sure to stop by.

Rupert, always loved him.