Lipton really was amazing at this. He lived to the age of 93 and passed in 2020. Glad his work will live on since he did it for 24 years.

More than a masterclass about Dave, this is a great insight on his brilliant mom! How accomplished she is! wow! Scholar, PhD pioneer, language erudite, all while going to Dave's stand ups as a teen (drive in, stay, drive home). WOW again! Hats off to Mrs. Yvonne Seon

Dave is so superior in every way. On every level. Never ceases to amaze me.

Real comedy questions authority & calls out hypocrisy. It provides society an invaluable service in this respect. Chappelle is one of the greatest in the history of the art form. Even going back to kindergarten, he was calling out green corn. That was just the beginning. This is why censorship & cancel culture is so insidious. We cannot silence our critics. We need the comics as part of our human experience.

I didn’t want this interview to end

Comedy 🎭 got me through some dark times in my life and will always be grateful for the art.

This is a brilliant way to conduct an interview. Just short, basic, simple questions, and then allow the answers to blossom into natural conversation. Very enlightening in a comfortable, unforced way.

The story he tells at 17:25 had a massive impact on my life since I first heard him tell it on this show a long time ago. I think not a week goes by when I don’t think or talk about it. A guy once said to me that if you are worried or fearful of something, then ask yourself, “If the worst possible outcome of the challenge you are facing happens, would you be able to get through it and handle it. If yes, then you should stop being afraid of the thing you’re facing. The answer is almost always ‘yes, I would still be ok if that happened.’” He called it the “Worry Once Method” for dealing with fear. It seemed that Dave figured this out in reality and not through a thought experiment. Thanks for posting this, I’ve been trying to find a copy of this clip for a long time.

I saw Dave Chappelle in a comedy club in San Francisco. He was the opener for someone else and he was so effing hilarious, the lady following never had a chance. This was before anyone knew who he was. We knew after that night. I’ve never seen a funnier comedian live in my life…

"What's going on? Nobody knows. Those people aren't crazy- they're strong people. Maybe the environment is a little sick."

Lipton will always be one of the greats! One of the best interviewers to ever do it.

FYI - this aired Feb 12, 2006. The full episode is 90 min.

This was many years ago but I enjoyed seeing it again very much. Thank you.

I love how Lipton puts ALL of his guests at ease ❤

A strong family background, his intelligence and comedian genius is a blessing. Such a sharp mind that’s attractive.

Chappell is a national treasure ❤

Professor James Lipton was an icon and we miss him a lot.

This is just proof that Dave Chappell is a true genius.

best DC interview! Lipton was so impressed by him, that he chose Dave to be his interviewer some months later when he was the guest.

Comedic genius.

Thank you Dave for your brutal honesty. I know this is old. But I remember this. And we pull from this today. These future actors need to stay grounded. The best in the business.

Really miss James Lipton.

Turning anger into 🎬, years to gain intelligence best served through scripted fearless comedy...genius

This era felt like being released from history. Black and white were becoming so much easier to juggle. Didn't last of course.

I've never seen this, this is such a gem. Thank you for the upload!

"Calling someone crazy is dismissive..." Dave showed me u can turn crazy into eyeballs 😳 and a conversation to boot!!

This has to be the best interview I’ve ever seen

White/Caucasian male here from Central/Eastern Kentucky. Of the entertainers that are on my bucket list of people I want to meet before I pass away? Dave is my #2. Morgan Freeman is my #1 and I don't believe Dave would feel offended in any way. I just hope I don't meet them at the same time. I'm afraid my head would explode.

the most shocking thing about this to me was the chemistry between Lipton & Dave. I always thought Lipton was a little uptight and too serious. He was loose and ready for comedic banter.

I remember being really into Actors Studio at this time, and Chapelle on here really added to what I thought of the Chapelle show

Dave is spot on with telling time by TV! I knew when Walter Cronkite came on it was time to get ready to catch the bus for kindergarten 😊

Its the real Dave...look at the smoke

What an amazing mother.God bless her.Dave your pops isn’t to bad either

So honest, Dave is a genius, James Lipton does his research, he knew more about Dave, than Dave. This was an excellent interview, it almost was like Dave and Lipton rehearsed, but I know that did not happen. Thank you for this clip.

That damned green corn Fd everything up😂

Dave Chappelle show was fun nominal. It was just filled with brilliant and acting scripts.🤔👶🏽🧒🏻👨🏾‍🍳👨🏼‍🏫👨🏾‍🦱.

This is interview is amazing. Excellent

I'm always amazed by people that can remember specific details about their life from age 5, and earlier. I think those people have brains that work in unique ways and are typically connected to society in a way that most people aren't. Clearly Dave is not typical.

That's the real David Chappelle, James Lipton is fun

Have loved Chappelles comedy for so long and looking at this video makes me think that the big difference between Chappelle then and today is that he lost his battle against the system. What he said back then used to be so provocative among so many that just followed a scheme planted by the industry and a system that he seemed to be against. But it must be hard to be against when it is so lucrative to be a part of it, I imagine.

This intro felt like SNL - "...from Men in Tights...........to Undercover Brutha....."..... Thespian !!

Dave is famous but he is a soldier/worker bee just like the rest of us. This is very unusual for someone like him to be so open and honest. So respectable! Great interview!

I truly believe the Dave we have now is not the same Dave

Alcohol is good for war. WEED is good for peace. Dave Chappelle is truth to the heart. They never gave me a penny for the Con Air idea either.

This is the REAL Dave Chappelle. His voice, build, and skin tone is my evidence.

2 absolute legends

One of the best ever

😁_ Smiles stand to the top. I agree as laughter catches the heart to follow proof in passion... As I'll never stop my passion with showing a Smile for my representation & who I love to be with!!! I did laugh at this video and I do think your Fabulous too!!!❤ Thanks for making laughter follow you & a smile to prove this from all that interacts with you anywhere😁😁😉😁!!!

Dave. Good People.

Lipton was THE MAN! And everyone knew it.

I am enjoying this very much. Wow. Did not know his upbringing. Love Dave Chappelle. And still cracking up those jokes in between the questions which is a testament of his talent always ready to go.

0:56.. The Real Dave Chappelle 👏👏👏👏👏👏 What we got now ain't no Dave Chappelle Look at the honest love from the crowd and the humility of Dave.. so beautiful to see.

2008 ("4 days ago" thanks)

Will farrells james lipton impression is so legendary

Reggie Warrington is the reason my tape broken I absolutely love that part!!

This is the most amazing thing iv ever seen

That standing ovation about Hollywood was awesome!

Such a welcome 🙏 break From the mindless drivel, that populates our discourse ❤❤❤

Another GITMO LEGEND

At 25:05 Chappell drops da bom. Lipton can dazzle everyone with his bow downs and adorations and it works 95% of the time. They are eating out of his hand. But, Dave throws that hook and that bearded chin takes it hard, all 4 knuckles. Chappelle is No Fool.

Great video. Love them both.

Great interview

This is gold.

I cried my first day of school. I think it was because i wore rain boots and didn’t have other shoes with me. I’ll never get over that.

Wow, it’s been 18 years. No wonder he’s so smart, his parents are both very intelligent. His kindergarten experience was exactly like mine-with the exception of wetting himself.

geezz, i thought it was some AI cr.p jjjjj but Dave was there for real....with Lipton ! great Dave!!!!

Wow. Two geniuses!

I watched this all the way through w/o realizing how long this video was.

This has to be 2008-2015, Chapelle Show ended in 2006 and he moved to Africa, disappeared for about 6-8 years, and then around 2016/17 his first Netflix Special dropped. This is after Africa, but before Netflix for sure

Great interview-thanks. I’d love to see the other half. Do you know if it’s available?

Damn. I was really enjoying that

We need another Chappell show!!!

Saw Lipton once in a NYC restaurant. He was sitting with Kirk Douglas

the rest of the interview was daaaamn good as well

it took 5 or 6 viewings of fear and loathing until i realised who was playing Raoul Duke. i never knew Dave was Reggie because i only saw the character not the actor and now that i see it, i can't bloody unsee it. i think that's what marks a maestro from a brick layer, they don't leave any trace of themselves, dedicated to the craft, smoke and mirrors.... a fine, fine entertainer that Tyrone Biggums......

This interviewer is absolutely amazing, short quick questions then he goes quite and allows Chappelle to just talk and it worked so well here.

Interesting rewatching this interview nearly 20 years later, im now older than Dave is in this video, he seems so young here, but its not how i remember watching it the first time

So special

Mr.Lipton🎉❤

Dave gives Lipton the finger'! 😆

No wonder Dave Chappelle is so cerebral. His parents poured into him.

Stay real Chappelle

Lipton did his research

It's super old this was when Dave wasn't on steroids he was tiny back then

Lipton is always on point.

3:08 dave's mother was hired by Patrice Lumumba. that's huge!

I love that Dave kept succeeding despite Holyweird.

Years ago, I thought KZfaq was the greatest thing in the world so much great useful, educational, entertaining videos. To me, I felt more engaged and connected to the source because it could’ve been someone like me just Watching and wishing I could do that stuff as well. I don’t consider myself By any means😊

I’m glad he doesn’t do this voice anymore. I remember hearing him on Howard stern and hearing him use his actual voice and being like”who’s that?!?”

Oh WOW! ….this is an excellent interview. It’s great to hear Dave tell about his life. 🌞❤️

A jester who flouts every court... Hmmmm

Some scary stuff, and a scary world

Rip james...

Just because he's a comedian the audience laughs at everything even when he's not joking.. if i said i hated school, no one would laugh.

This is an edited version. He has some great quotes throughout.

I hated for that to end.

One step down from the Kennedy Center. One step away, I should say.

This was one of my favorite, and even when Dave came back to interview James, that’s something to look into. Very funny, but if you know James Lipton, it’s interesting. Good watch either way.

Is there not a soul that has the 200th episode where Dave hosted the show? Why did my old harddrive have to brick, both of those full exntended epiosdes I had were some real gems and them bravo had to mess it all up by putting copyright claims all over them and couldn't even be bothered to upload he episodes themselves.

“So colour was always an issue?” 😂