- Himself - Host: we've got a lot to talk about, I haven't seen you in a long time. First of all: what've you been up to? What's Dave Chappelle been doing for himself?
- Dave Chappelle: [after an audience member yell "Season 3", referring to his variety show Chappelle's Show] nothing, there's a guy yelling out "Season three"
- Dave Chappelle: [after applause and laughter from the audience, referring to his sudden departure from his variety show causing confusion among the fans, from the network and their attempts to bring him back] nice try Comedy Central
- Himself - Host: [jokingly, impersonating a television show executive] that's one of their executives, we need the dough, come on
- Dave Chappelle: I've really been just relaxing and trying to stay out of trouble
- Himself - Host: right
- Dave Chappelle: being a celebrity, your realm of getting in trouble is worse than the average person
- Himself - Host: uh huh
- Dave Chappelle: the average dude got to go out and look for trouble. I'd be sitting around, minding my own business, a dude be like" hey man your Dave Chappelle"
- Dave Chappelle: I'd be like, "what's up man?" Then his like "I got twelve naked bitches and a hot air balloon. Do you want to go traveling with me?"
- Himself - Host: [after applause and laughter from the audience] call me next time, I need to get out of the house once in a while
- Dave Chappelle: yeah, I just stay in the house and it's funny because when I come here, everybody screams but when I go home, it's not like that
- Himself - Host: that's the important thing to remember because when you go home it's a different situation right?
- Dave Chappelle: [impersonating his kids] oh my kids don't even care, "oh Mr. Promise is back from the road, did you forget all the toys you promised us?
- Dave Chappelle: [after applause and laughter from the audience] call and my wife's been a little "salty" at me
- Himself - Host: she's not happy with you right now?
- Dave Chappelle: she's not mad at me but don't think you can walk away from $50 million and your wife is going to be cool with that.
- Himself - Host: [after applause and laughter from the audience] that's an angle I hadn't thought about
- Dave Chappelle: I thought I was going to get the "Jerry Maguire you can be anything you to" speech, it didn't "pan out."
- Himself - Host: no?
- Dave Chappelle: [referring to Prince's album and a song within that album] it was more like Purple Rain around my house. I know what it sounds like "When the Doves Cry"
- Himself - Host: [after applause and laughter from the audience and Conan] ok I've known you for a long time, you've been coming on our show for a long time. I bumped into you sometimes on the streets in New York. You're a very "down to earth" guy. You really do seem like your unaffected by this, do you think that's fair?
- Dave Chappelle: I'm a little weird but I'm "quirky"
- Himself - Host: yeah
- Dave Chappelle: but yeah, my life's pretty normal. I get amazed by this too, I was in LA for The Grammys, I'm on TV in a t-shirt right now so I had to get some nice clothes for The Grammys, so I went to one of these nice Beverly Hills store, there was a restaurant inside the store. I never ate soup in a clothing store before and it was real "balling." I look across the room and I see Jessica Simpson.
- Dave Chappelle: [implying he was talking and thinking to himself when he first saw her] I was like: wait a minute, I'm famous baby
- Himself - Host: [after applause and laughter from the audience and Conan] that's right, you go up and say something to her
- Dave Chappelle: that's what I decided but I don't normally do this but it was Jessica Simpson but let me see what was going on. I went to her and said, "hi Jessica Simpson, I'm Dave Chappelle, I'm on TV too"
- Dave Chappelle: [after applause and laughter from the audience] and she was like "I know who you are"
- Dave Chappelle: [after applause and laughter from the audience] I was like "I knew it bitch!"
- Dave Chappelle: [after applause and laughter from the audience and Conan] I didn't say that to her but I got excited
- Himself - Host: [after applause and laughter from the audience and Conan] yeah you got excited, sure
- Dave Chappelle: it was a bit corny but I was like " I'm a big fan of your work", which felt weird saying because that's not true.
- Himself - Host: [after applause and laughter from the audience] right, right
- Dave Chappelle: [to the audience] I'm not "dogging" her music. I don't know her music. I'm talking about her "Newlyweds" show, I've been a newlywed, it's nothing like that show.
- Himself - Host: right, right
- Dave Chappelle: if I made a show about my first year of marriage, it'd be called "Bitch you tricked me."
- Himself - Host: [after applause and laughter from the audience and Conan] you're a romantic fool
- Dave Chappelle: no, I love my wife, I'm crazy about my wife
- Himself - Host: yeah
- Dave Chappelle: [referring to Jessica Simpson] the crazy part was that she was really nice
- Himself - Host: yeah
- Dave Chappelle: [to the audience] if you're a fan of hers, you'll be happy to know she was great
- Himself - Host: yeah
- Dave Chappelle: when I sat back down to finish my soup up, as she was leaving she came up to me and said "bye Dave Chappelle, it was nice to meet you," and she gave me some "sugar"
- Himself - Host: she gave you a kiss?
- Dave Chappelle: [jokingly] yeah which was crazy, I opened my mouth a little bit
- Himself - Host: [after applause and laughter from the audience and Conan] yeah you did what you had to do