How Chris Rock surprised audiences — and himself — with 1996's Bring the Pain

W. Kamau Bell never got a chance to ask Chris Rock about his 1996 HBO comedy special Bring the Pain while they worked together on 2012's Totally Biased, FX's Daily Show-esque comedy series examining current events, which they co-created.

That all changed when Bell, host of CNN's Emmy-winning United Shades of America, was asked to direct an episode of A&E's Cultureshock, produced in association with Entertainment Weekly, about comedy. He quickly narrowed his focus to one man, one singular moment.

"This is a long time coming," Bell tells EW.

And a lot of big names — among them Conan O'Brien, Ava DuVernay, Martin Lawrence, and Oprah! — sat down to discuss Rock's provocative and critical look at race in America, tackling the O.J. Simpson double-murder trial, "black people vs. n—s," and more, including the Bell's one burning question, which you can see a bit of in the exclusive clip above.

Below, Bell discusses in depth his desire to know more, what it was like watching Rock re-watch the 22-year-old special which earned him two Emmys, how he thinks it ultimately "shocked" our culture, and more.

ENTERTAINMENT WEEKLY: What makes you the right guy to tell this story?

W. KAMAU BELL: I would say I was born to tell this story, but that's probably not the answer you want. [Laughs] I was in a pretty fortunate position… Morgan Spurlock had directed my Showtime special — I asked him to do that because he had never directed a comedy special before — and he came to me and said he has a series of pop culture documentaries and he thought I should direct one. I was like, "I've never directed anything." He's like, "You'll figure it out." Then I got to work with this incredible producer, Jamila Wignot, who has worked with Henry Louis Gates and all sorts of heavy-hitters and really helped me learn how to direct while I was directing. I put a lot of this on her. She really helped me not go down the wrong path for too long and also respected my vision. Without Jamila, I don't think I could have pulled it off, so I'm trying to give it up to the people who had patience with me.

When it was asked, "Do you want to direct a documentary about comedy?" the first thing that came to mind was Chris Rock's Bring the Pain, and a lot of it is because I worked with Chris on my first TV show, Totally Biased, and the whole time I was like, I really just want to sit down and ask him questions about Bring the Pain, but we had a show to make, so I didn't have time to do that. So this is a long time coming.

Oh, so the fact that this focuses solely on Chris was your idea?

Yeah, when we talked about the idea of directing a documentary about comedy — and there's a lot of things I could've done — I was the one who was like, I want to ask Chris Rock questions about Bring the Pain. [Laughs] That was basically my pitch. But then it became, well, can we get Chris? And I hadn't really talked to Chris much since Totally Biased had ended, but we were still friendly. I was like, well, I know he doesn't do things just for fun, he'll only do things that he thinks are worth his time, so luckily he thought this was worth his time. Once we had him in — there hasn't really been a proper celebration of Chris Rock, so I think I'm pretty lucky that I am first to market. He was on Oprah's show — I think him and Celine Dion have the record for most appearances on Oprah's show — and so, I kinda think I was lucky that Oprah [wasn't like], "Oh, another documentary about Chris?" She was like, "Oh, I've never talked about how much I like Chris!" It truly opened a lot of doors for us just because nobody had done it before.

What was your No. 1 burning question about Bring the Pain?

The Marion Barry joke, because I knew that he had to have written that very close to the — I knew as a comic that he had probably toured that act around the country, and you can't be in Dayton, Ohio, opening on Marion Barry because they don't have the same relationship as the people in D.C. did. So I knew that joke had to be one of the last things written. I also knew he had to go out there sort of nervous that maybe it wouldn't work, so to open your special on… A lot of comics open their special on, "Hey, I'm in Cleveland! What up, Cleveland?" But he opened his special going to the heart of the matter for that audience in D.C. — a black, middle-class audience. And I know Chris is somebody who rehearses a lot and will really work jokes over and over for like a year before he gets them ready to record, so I was like, wait, he couldn't have done that with that joke — even if he had done that same joke about Marion Barry in Palm Springs, they're not going to give the same reaction so you're not really working on it. To me, that was one of the ones that I was like, "How did that joke come together?" He told that story … and it's a great story to think about him following Mitch Hedberg in a comedy club, to do that joke.

You watched him re-watch the special — what was that like for you?

We saw him right as he was toward the beginning of his tour that ended up being Tamborine, his Netflix special, and so we had gone to the show the night before just because we were in town and he let me and the producers come see it. I could see him still working stuff out, so it was funny to see him watch the Bring the Pain clip and it was some stuff he hadn't seen in a while and he was sort of like, "Man, I wish I was that funny now!" [Laughs] He was really looking at it kind of like I would imagine Michael Jordan would look back at clips of him in the '80s. But the difference is, comedy's not the same [as an] athletic career — there was sort of a sense like, Oh, I need to get back to that funny. I can get there. But by the same token, he was kind of looking at it like, that guy's funny — he was sort of looking at it like it was a different person, and he says that in the special.

Right, he says, "It's like another person did it. I guess another person did do it."

Well, he was a guy that was younger, he was newly-married or about to be married, he didn't have kids, and also it was the '90s… [Laughs] It was a different time in America and in his own personal life.

The title of this series, of course, is Cultureshock and it examines moments that had a big impact on pop culture. While it doesn't really like it seem Chris' intent was to shock, but just tell his truth, that special was a major moment in stand-up comedy, and beyond. As a fan of the special and now getting to talk to him and all of these great names in comedy and media, what's your big takeaway from making this?

I think the thing I took away from it is that Chris, at that point in his career, wasn't going outward, he was going inward. He had gotten his big shot at SNL, he walked into that thinking it was going to be his big break, and it kind of wasn't – in fact, it kind of worked in reverse in that some people had a less-than opinion of him after SNL than before because he just hadn't popped the way that Eddie Murphy had, which we also talk about in the special. So, the thing I took from Bring the Pain is that he was really trying to figure out, What do I want to say and how do I want to say it? And also — which I think is how most great art works, from the inward instead of outward — this is kind of a standard thing in comedy, [but] there's sort of a stage in comedy where you're trying to do what the audience wants you to do and you're trying to shock the audience, where really Chris was trying to surprise himself. So ultimately, in trying to surprise himself and push himself, it ended up that he was surprising and pushing all of us. He didn't go up there on stage saying, "How can I shock these people or how can I offend these people?" He was like, "How can I say something that I haven't said before? How can I put this in a way that I feel like I'm not hearing it out in the world?" On top of that, I think it's also about being an honest self-critic of yourself, so when he was out there in the world and suddenly he was following Martin Lawrence [laughs] and he bombed, he didn't get mad at Martin Lawrence, he got mad at himself.

Cultureshock: Chris Rock's "Bring the Pain" airs tonight at 10 p.m. ET on A&E.

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