Watching these made me realize just how rehearsed the "couch interviews" are, but that's not a bad thing because these are two comedians working together to make a bit that will make people laugh

And, yet again, they did not plan anything in advance. You can keep claiming they did, but They. Did. Not. As I said from the start, there were agreed-upon talking points. But that occurred between Chappelle and the show’s Segment Producer. The resulting notes were then provided for Letterman, who then took it from there during the actual interview. Did both Dave’s meet up beforehand? For the 10th time, no.

@Don Giller maybe "rehearse" is the wrong word and I apologize if that's giving the wrong impression. I think what I'm trying to say is that he worked with chappelle in writing out an entertaining segment before they say on the couch to talk

Point proven at 47:44, Chappelle is on his fifth or so appearance on the show and Letterman asks him "are you originally from Ohio?" when he knows full well that Dave is from DC because he's asked him almost every time he's been on before. It's all part of the bit, they are working together to create a good setup and punchline for jokes between each other because there are only so many minutes of air time they will have before a commercial break. This is two comedians working with each other before the cameras roll so there's an entertaining segment for everyone who watches and I think it's fascinating to recognize these things so many years later after watching comics work for so long

One last time: Letterman didn’t rehearse with his guests. Ever. In fact, after his quintuple heart surgery in January 2000, he stopped going to rehearsals, period.

@Don Giller dude just look at how in the early interviews it's clear that between the two, Letterman sets up a question which leads to Dave giving a punchline. Which then Letterman has another question perfectly setting up another punchline for Dave and on it went. That's how tv went back then with unknown comics getting center stage on a huge nationwide tv show, it goes all the way back to Johnny Carson. They at least rehearsed the beat by beat comedy once beforehand, because it's television and they wanted to get it right when it's showtime. The laughs of the host and guest are real and what have you because it's legitimately funny, but this sort of thing was how it was done for decades on tv. Nothing wrong with it as I've stated three times now, and if you can't see how it's been "rehearsed" at least once in some mild way then I don't know what else to tell you

I wonder what happened to the Ashton Family tho🤔

I miss both Dave's

39:22 - We are still over there... Hmmm..

Bass player was jamming....but you can't even hear it!

Letterman was on fire here

Meh. His sketch comedy is great, his stand up is ok, but not great.

U can gradually see his rise through his wardrobe!

never call the cops!

You do fit a description....LOL

he really grew into them teef

so cool to see the respect that grows between these two legends. You could tell Letterman liked him immediately. You can also see that Dave Chappelle worked his ass off to become as successful as he became. So much respect for both of these guys. .He was hustling at 20 years old. Its very impressive

He tried many of those jokes we love on Letterman first.

Nice To See The Real Dave...I Sure Miss Him !!

A very logical well educated man on life Who has morals pride and a character like no other bless you

Wow, Chappelle's commentary on the build up to the Iraq war was so spot on.

Bless Dave chappelle

came for Chapelle, came back for the Ashton Family

Holy shit that hour flew by

Maybe Chapelle's slyest joke ever: "They stole my car...it was a rental car, but, it still Hertz."

Classic how Dave have Whoopie Goldberg laughing so hard 🤣😆

Thanks Don

Two greats. The level of mutual respect developed over the years between them is awesome to watch, especially when comparing the last interview with Dave's first appearances on the show. Great video thanks for sharing.

THE 🐐!!!

The older he gets the more handsome he looks.

Dave reminds of the mayor from back to the future.

This Dave looks so different

I could listen to Whoopi & Dave talk for hours.

"Whopper with cheese" 😂😂😂 I see where that Half Baked scene came from.

I always loved the chemistry between chapelle and letterman

Man looks like 3 different people. What happens to him? Way less agile in his movements and his voice changed drastically.

Clayton Bigsby brought me here

Huge credit to letterman helping early days Chappelle

Damn. Suspend 23 times during black history month. Poor guy.

He is so funny. Really I'm here alone just laughing my ass off. Lucky no one is here because now I can't find it.

Wow, as far back as 97 New York crowds got uncomfortable with Daves material.

those 2004 jokes , most people never heard...work in 2021..that's what makes great jokes...there timeless..

The greatest to ever do it

I could listen to this man talk for days. What a class act

His interview with Whoopi was best

The best thing about YouTube is The Dave Chappelle Show 👍🇦🇺

The guy has come a long way. Respect brother!!!!

Love the video! So crazy there was a time you had to publicly deny marijuana use for fear of self incrimination.

The greatest thing is seeing how these two slowly aged as the years go by 😂👌

Dave Chappelle is comedy genius and so much more. I'm in awe of this collection.

I have never understood the fascination with this guy. He's funny in very few parts but overall I never found him overly funny. To each their own I suppose.

His Colin Powell is Eddie Murphy's Whit guy voice

48:06 best part for me. The band picked up on that perfectly.

Does anybody know the song they play at 15:21 and 21:07?

Thanks!

"Crying in the chapel"

1:06:00 It's not the end-all-be-all. but there are things in my life that I did not purchase with money that are very valuable.

I love skinny Dave Chappelle. Age 20 and streets ahead of many seasoned comedians.

That first interview was the shortest I have ever seen. Was that the whole interview?

@Don Giller I guess so, but the next 3 were even shorter. It just seemed odd that the man tossing a woman around on his feet got more air time at the end of the show. I was thinking that maybe Dave's skit went a little over time.

Post-stand-up panels were commonly perfunctorily, especially with unknown comics.

I didn't realize Dave has been doing some of the same jokes for over 25 years he just got more comfortable and better delivery. Cannot get enough of this man

I love how even Letterman’s ultra-seasoned, extra-professional, super-versatile house band struggles to play the intro to Steely Dan’s “Josie”.

"A STAR WAS BORN" "I've been black four life times in a row". The G.O.A.T! 🐏 Watching his performances not only do we laugh out loud, we get a history lesson!! Kudos Dave!!!! 👏👏👏

Watching them from young to old, the way they talked, their looks.. that's the living prove of time in life. Two legendary Dave shook hands in the end, that somehow gave me goosebumps. What a moment.

Nice suits!

I love Dave. Cool to see in this retrospective how he has honed his bits over the years, delivering the same laughs with even fewer words... Real craftsman trimming it to the bone.

I love comedy & I'm finally taking a longer look at him. Never grooved on racial humor which so far seems to be his thing. Keeping an open mind. Update: 3rd bit in my life watching - still racial which is not fun to me He is very talented & the delivery is there so I get how he's funny. Update: into the 3rd bit a few minutes - warming up to the humor - starting to be humorous to me a little bit. He is so brave so young to do this! Smart dude! He is definitely lovable feeling so I can see watching & being into it just for him. But if it's super duper racial I won't be into it. The first bit I saw was on Star Search! Amazing he was on there. So rad. Very brave. UPDATE: 18:33 VERY FUNNY - enjoying this - racial humor coming out of his mouth is actually pretty funny I'm learning 21:00 - I had no idea he was an actor no kidding I never saw ConAir - I missed this whole area of pop-culture. 22:27 - FINALY something I can relate to - the commercials yes lolol good one dave 23:59 - "some people say I do too much ethnic material" - funny I was talking about that but I didn't say it was too much. That's judgmental. I was open. I knew he'd win me over probably. He isn't at the top this long & be like this this young for nothing. I could see from just a few minutes that he lived some interesting stuff and probably has stories and this is how he came to do what he do best. Pretty awesome. Smart & brave dude. I don't know how I missed him as I used to like Letterman a lot. But I was watching Dave when he was throwing pencils at cameras lol. Edit: 28:00 AH he is mainly an actor it sounds like - I don't watch all that many movies - how I missed him I was riding the Letterman, Cosby (hell no not no more), then Seinfeld, Carlin, then Larry David & now Bill Burr, Louis C.K., and many more. I look forward to explore more of Dave Chappelle stand-up! "Sit Whitey! Roll over Whitey! Bad whitey! Bad whitey! Get me a job!" HILARIOUS funny man 40:30 - war stuff - what the heck - now I'm annoyed I have not known him until now - SMART - love this guy!!!! LOLOL yay! pretty good I hung with him this long and keep going - 2nd date heard! lol 43:30 - I make jokes daily - nice

Wonder if he went to the crossroads.....

Woops What you say keep it respectful oh ya,,

Big probs to Letterman getting Dave Chappell publicity in his early career

Thank you for the upload. Great compilation. 👍🇮🇪🍀😁

Two comedy icons Dave & David

I think Dave is the most talented comedian ever ..

David Letterman always adored smart people like Dave Chapelle👍👍

20:12 the cleanest dap up you have ever seen by letterman

Letterman knew a ⭐ when he saw one. Leno just shuffled them out and hoped one or two hit.

Great job ❤❤❤❤

The last interview really shows Letterman's nuanced skill as an interviewer with his ability as host to draw out so much insight from his guest, as well as the graciousness and intelligence of Chappelle.

@Don Giller you the 🐐

Whether you agree with all his points, he is one of the great philosophers of modern times.

I was at that gig he's talking about in San Francisco. It was at the Punchline. He was the funniest comedian I've ever seen. I was laughing so hard I couldn't breathe.

Did he ever actually take a sip of his drink..he picked it up like 20 times

What is the name of the intro song they played at the start of this whole clip?

Ian Hunter, “Central Park ‘N West.”

Dave chappelle is indeed culmination of class acts. His remarkable wit along with effortless way of being wise just amazes me. In addition, he has indeed progressed remarkably maturing as a person and an iconic comic brave enough to take on cancel culture so bravely in recent years.

DAVE IF YOU EVER READ THIS. YOURE THE GOAT. AND REMEMBER KEEP YOUR HEAD DOWN AND RUN IN A ZIG ZAG PATTERN!

he started off trying to sound like chris rock, he looks so young

You can see the progression of his jokes

Dave we pray for u

The more I see of Dave Chappelle, he 's easily the most astonishing stand up artist I have witnessed in my four decade lifetime

Dave Chapelle pretty much grow up on this show. It was nice to see

"They stole my car. It was a rental car, but it's still Hertz." Lol

Wonderful to see his evolution. This is a perfect video.

I'm so happy for you. You make me proud when I see my brothers suceed

never noticed the similarities between young dave and YNW MELLY

When you keep getting invited back...speak volumes. Dave C started out as a rookie and became one of the 🐐. Letterman was a brilliant show man!!

This is amazing

That joke about police in England left me in stitches 😂😂

Dave Chappell is the funniest man on the planet today

This is great, thankyou for posting :)

The funniest guy to ever tell a joke.

It's funny seeing him test the Half Baked fast food bit in stand up.

That last episode gave me weird vibes. Much more serious, more of a interview than comedy.

43:40 he barely even promoted his show no wonder why it only lasted two seasons

A little homework may be needed, if not you may break the internet with that one

Would like to see the camera rolls from the camera he walked around with on his neck

Dave have always challenged the status quo

Watching Dave grow up ...again i saw him in DC early .. and seeing polished Dave is why i loooove YouTube.

Glad I found this. It's like a hidden special. Never seen him with hair lol

Who remembered chappelle was in con air? Not me