Fun With Rupert Jee | Letterman

Rupert Jee goes undercover while Dave tells him what to do and say.

#RupertJee #FunWithRupert #Letterman

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Welcome to the Letterman YouTube Channel, home to all your favorite clips from Late Night and Late Show - as well as conversations with the writers, producers and performers who helped make it all happen. These highlights have been artisanly-produced, carefully-curated, and chosen completely at random by an old computer that used to pick numbers for the New York Lotto back in the 90’s.

[andygonsalves]

Easily one of the funniest things ever seen on television.

[michaelb]

2:10 they cut the best part when he then goes to the staff to report “that lady’s stealing napkins”

[tresadrienne]

omg me and my brothers would be crying with laughter watching these back in the day. Classic Dave!

[infowarriorone]

I remember when these first aired, unbelievably funny stuff. Just listen to the audience reaction. I miss Dave.

[dmblum]

Dave is such a comedic genius when he improves to the rubber gloves.

[billyb]

I remember seeing this live in 1993 best ever Rupert Jee!

[gigatremor]

I need to find more of these clips, this is gold.

[orangeclover]

More Rupert! I thought I'd never see these again!

[Brian_C_]

I laughed throughout probably 90% of the 3:44 runtime. "You ever see The Jazz Box?"

[BobbyBoatman]

Rupert was freaking awesome. The best.

[SubtlyAggressive]

2:27 - You can almost tell he was trying to say that under his breath so as not to alert the people he's interacting with LMFAO!

[shyster]

More Rupert and Can We See Your Photos Please!

[amppma]

I'm laughing so hard my stomach hurts. god, this was such a great show!

[oledame]

This is so good. My favorite show of all time.

[tbx]

One of my favorite things about a trip to NYC was buying a couple shirts from Rupert.

[rocketreindeer]

They might not want to, but I'd like to see those two women reflecting back on the time they got so damn annoyed. My Aussie friend thought Rupert was gonna get bashed when I first showed this to her, so maybe they don't remember it with the same level of hilarity. But it'd sure be interesting.

[jfleck]

The premise and execution of this gag are top notch, big fan

[lloydstuart]

Dear David Letterman we miss your shows you were so entertaining and funny

[pamr]

I remember this so well and knew exactly how it would go…I still laughed like it was the first time I saw it.

[Despond]

It was funny, but the thumb in the glass made it hilarious.