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During all my children and one life to live

The check for ruperts that he didnt know about lol

At the end, he asks the kid what his name is. Wanted so badly to hear, "My name is Chief"

That’s funny

This is particularly funny to me, because my mom would have won this game in a _heartbeep_ back in the day. Whenever I went out with my parents my dad would ask my mom "Well where to chief??". Suffice to say *she* *hated* *it* .

pervert dave

More proof the 90s were the most golden of all eras. I absolutely adored Letterman.

What’s does well for you chief? Being lazy 😂

Rupert’s face when he said “gift card to Rupert’s Deli” hahahahhaaha

Hey! Wasn't Rupert supposed to wash his hands before he put on the gloves?

All you can eat at Rupert’s deli!

Rupert’s innocent replies are too cute!

Nice little bit of racism

Or buddy

That kid seems like such a nice guy.

Rupert never GAF and that's what made him so funny.

Is the Hello deli still around?

"People from New Mexico." Damn. This was one of my favorite bits.

Rupert seemed very low-key mad the entire time lmao

This segment slaughters anything you see on late night TV in 2024. Rupert alone is a better co-host than we have frigging hosts and he was just a part of a tiny segment. Take me back damnit!

Wheres Sirajul and Mujibur?

I miss Dave..and rupert..they were so good together... those were the days !😊

Such a dumb time wasting skit but its a good way to get audiences

LARGHETTO !!!!!!!!!!

how has this not been won? the crowd clearly knows why they are there. you should know before going in

I was never at the show. But I dreamt that Dave and I were buddies. He’d visit me and then bring me to NY to hang around backstage and we’d talk about stuff after the show.

That looks like a good sandwich

Id kill for that Corndogus Eternus shirt

Please don’t call me Shirley

I once kept calling a bartender 'chief.' He didn't think it was amusing.

Gilbert Gottfried was mistakenly thought to be Rupert on numerous occasions

That sandwich looks so good

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

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

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

5:05 he’s trying to ask why yer calling him chief but rudely interrupted by the interviewer with his run on talking who apparently thinks the game should be changed to “could you be so quaint as to rudely interrupt me while I run on talk”

the happiest this kid's been in his life" Holding a cold sandwich and standing between two woman that are average looking in 2024 LMAO

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

5:49 the face 😂

They picked a high school kid. He looked kinda sheepish. Miss that show it was goofy and fun.

The girl on the right (holding the gift certificate) looks like Sofia Vergara.

Paul Schaffer least talented guy Dave could find, per Dave.

Stop Calling me Chief 3:03

🇺🇸🇺🇦❤🤍‬‬‬‬‬‬‬💙‬‬‬‬‬‬‬💛🌹🇮🇱🤍‬‬‬‬‬‬‬💙‬‬‬‬‬‬‬

🇺🇸🇺🇦❤🤍‬‬‬‬‬‬‬💙💛🌹🇮🇱🤍‬‬‬‬‬‬‬💙‬‬‬‬‬‬‬

Dave made the simplest, everyday occurrence funny.

Whatever happened to that dude?

I miss this era of the show.

The two girls were beautiful.

Does Rupert still sell cigarettes?