he totally peaked in robin hood men in tights

Dave Chappelle was born exactly 50 moons after me. Preeeeeetty sure that means he owes me some money!0)))

DC GOAT

His white people voice changed through the years lmao

Pete Davidson must have copied his mannerisms from young Chappelle.

Damn!! I just love Dave Chappelle!♡

Which Dave r the ppl in the comment section talking about? Food for thought.

love u dave

OMG Dave Chappelle's teeth, did he grow into his teeth, or did he get work done? The first video clip has to be the oldest footage of Dave Chappelle I've ever seen, and I've seen him on Star Search

I found myself too sharp and alert .. :D

Besides Dave being on point I usual I laughed probably the most of the Ashton fAmily that truly caught me off guard. 🤣

Fabulous! Thanks for sharing!!!

96 was like Dave’s revenge

IDK if it was Letterman's booker or Chappelle's agent but he seemed to be paired with beautiful women every time he appeared.

Dave doing jokes almost 30 years ago that people do variations today. He's the GOAT.

He still doing thèm too

i love Whoopi's laughter.

Did he call whoopi Oprah ?? 🤣

ahh, he was a good kid. I can't believe how fast we all get old and jaded :/ Rock on Dave!

Watch his suits get better and better, lol

...I wonder if The Ashton Family still flips themselves👁👁

He just kept getting better and better

Whoopie looks like a krs one sister

if these are all his moments on Letterman, any idea about the 5 and 10 year gaps in appearances?

now that was good

Thank you for this great compilation of Dave Chappelle’s letterman interviews.

This is becoming my fav video in all of youtube 😂😂😂😂

Dave and Dave's handshake at 20:18, that shit was solid. Just saying, compared from the first after-set interview where he took Dave's mic, to there with the smooth grip, respect was earned. 💯

Finally David gave Dave a little sit down on his third trip up. Nice!.... Huh??

lol

2014 Dave was such a pleasant calm and well thought through Dave.

When he walked in when he did the Chappelle Show w Whoopi. You can tell he had no idea what was to come. He was happy people trusted his vision.

Whoopi Goldberg interviewing Dave Chappelle at Letterman show..... AMAZING

Thank you youtube. No. Thank you NBC fired employee.

If by any chance you might be referring to me, I never worked at NBC or CBS or for Dave in any capacity whatsoever.

2 of my favorite.letterman and chapelle.

This is great I noticed the band would play "crying in the (Chappelle) chapel" on his 3rd & 4th appearance etc

This was amazing. So grateful you put this together :)

"I get uncomfortable doing ethnic humor people are taking it to seriously.." 🤔

You never know when a kodak moment will come. Loved it. He implement his joke in real life. 😮♥️❤️ Amazing

Best comedian in the world

1st time I saw Dave was in 'You've got mail'

21 year old Dave Chapelle

Shucks

Dave Chappelle in SUITS!?!

Dave is the only comedian who can cheer me up when i have a bad day 😂😂😂😂 love this guy

Whoopi can't keep from laughing her ass off

You have to have MUCH love for David Letterman For seeing the genius and humanity of Dave Chappell!!!!❤️❤️

30:34 The Clinton’s were in Office at the time and I think most people really didn’t get the implication Letterman was making with that sedation/camp david joke.

WHO DOES NOT LIKE THIS VIDEO???

Wow Dave u were awesome even back then

Well, he definitely got better because those first shows... damn that was corny asf and all racial.. Damn Whoopi was an awful host...

Letterman what a Legend, what a Legacy 👏

i watch NUTTY PROFESSOR once a while, just to see him on stage. The only movie i watched more was SLAPSHOT with Paul Newman, but I am a Canadian and that movie is required viewing

🤗

Thank you

Absolutely brilliant

I love you

Thank you EVERYONE

At first I was like “How long do you have to have “Worldwide Pants” paused on the screen for it to burn in for a Youtube video??” But at least it isn’t the Fox News channel...😏

Watched the whole thing cause I thought there was going to be repeats. Surprise there was a whole hour of Chappelle with Letterman.

Never heard of buddies

I hate Illinois Nazis.

You guys are a riot

His sound effects are so good

He perfected all these old materials and turned it into a compilation of a beautiful art! God I love Dave Chappelle!

Superb upload! Chappelle you're a legend! Who on earth could possibly give this a thumbs down?? I'm truly baffled....

His timing and stage presence is awesome. Funny funny guy.

“it still hertz!”

Most clever shit ever

He was pretty much a pro from the moment he started doing comedy.

Do you have a Jimmy JJ Walker collection?

Not yet.

i did not know letterman ws s o much part of his coming to success and public exposure good call dave letterman

@dongiller many thanks for this. It's appreciated ❤️👍

hey! can someone please tell me if there is a compilatio of these lovely musical intros. or where can i listen to them.

Dave was adorable 🥰

He’s great, I loved the Dominos bit

Good stuff

Dave is incredible

That was pretty cool

Y'all got anymore of those Dave chappelio's

What I have is what I uploaded.

After watching these clips. .Dave is absolutely the best of all times. Hands down! I bow to ya. I just love it. So damn clever, and deep comedy and not that shallow low IQ stuff.

36.40 Whoopi losing her shit 💘 🤣😂🤣😂🤣🤣🤣

It was great watching Dave Chappelle growing up and also watching letterman growing old . Both going two different direction . Two great artists at there best !!!

Sad Dave didn’t acknowledge the coffee reference. He had a chance

DC is a true GENIUS!! He's not just a comedian; he's a TEACHER of truths which others see as funny!!!💕💯

Your absolutely correct port authority does smell !!!

Dave is my favorite comedian, hes a living legend

He was so awkward at the desk at his very first appearance.

SUBBED. Great upload.

One skinny brother

This is gold. Great video

Anybody knows the music at 8:15?

@سيف رائد جواد You're welcome. Take care.

@Ima Goyl thanks

Here you go. https://youtu.be/1VaEdKwXJhM

This upload is absolutely 💯 🔥 epic!

After Whoopi ,just golden 🤩

I like how David after giving a proper necessary introduction calls out "Dave" and he comes out😁😂🔥

GOAT

Look at him, he is such a young skinny thing! I bet his mom is proud. I would be. He's amazing.

Who thinks letterman loved Chapelle on his show because they have the same first name?

Two decades later we're wondering what must go on at camp david. Must be where the presidents' keep their stash.

The only man to speak truth. Boston loves you man.

He comes on talks his talk, Letterman laughs and coughs laughing.... Whoopi guest-hosts... He talks his talk, SHE cough laughs. Personally, I only cough laugh if it's truly funny and it snuck up on me. Young Dave is a guest on these shows with SEASONED comedians. Those aren't fake laughs! If it was basketball and it was a young MJ or Iverson I'd say the same thing, "Those aren't fake ankles he's breaking... He's that good!"

17:47 "...it was a rental car, but it still Hertz" Young Dave seems like he was TOO technical! Doing Jay Z, Eminem, Malice & Pusha T type jokes!

Chicken is like the biggest industry for food in the world before the conglomerate just started they put out the rumor that black people like chicken so much so chicken can get a buzz and people will think it's hip