Co-host Of 'How Neal Feel' & Co-creator Of 'Chappelle's Show'

Neal Brennan | Biography 2021

• By Puja Bhetwal
• Update : May 14, 2021

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Neal Brennan is best known for co-creating and co-writing American sketch comedy show Chappelle’s Show with Dave Chappelle.

Who is Neal Brennan?

Neal Brennan is an American producer, performer, actor, and comedian who started his career as a writer of the dating show Singled Out in the mid-90s. Jenny McCarthy and Chris Hardwick hosted the show. Then he wrote two variety shows for Nickelodeon, sketch comedy All That and teen sitcom Kenan & Kal.

In 1998, he wrote the movie Half Baked with his friend Chappelle. Later, Chappelle came up with the concept of a sketch show, and together with Brennan, started to work for a show. Later in 2003, the Chappelle’s Show premiered on Comedy Central and became the best-selling DVD series of all time at one point. Brennan was nominated for three Emmy nominations as a writer, producer, and director of the show. Two years later, Chappelle vanished, and the show ended.

Later, Brennan, DJ Douggpound, and comedian Moshe Kasherbegan the podcast The Champ (2011-2016). Wayne Brady, Chris Rock, Mario Joyne, David Alan Grier, adult film star Lexington Steele, rapper Too $hort, and professional basketball player Blake Griffin were among the show’s guests. His one-hour stand-up episode, Woman and Black Dudes, was broadcast in 2014 by Comedy Central. Also, in 2016, Brennan began contributing to The Daily Show with Trevor Noah as “Trevor’s Friend Neal.” Brennan debuted a brand-new half-hour of content as part of the Comedians of the World series on Netflix on 1 January 2019. Brennan has also appeared on Carson Daly’s Last Call, Jimmy Fallon’s Late Night, Lopez Tonight, and Conan, among other shows.

Later in 2017, Brennan was highly applauded for his second one-hour booth special, 3 Mics, in which he takes on three different mics to deliver diverse comedy: one-liners at the first; talking about tackling depression at the second and his relationship with his father at the third mic.

Since 2019, Brennan has been hosting a podcast called How Neal Feel and started guest discussions on various subjects, including current events, race, gender, sex, and technology. The first episode aired on 27 April 2019. Every week, he co-hosts the show with Bianca Sia. 

Brennan also has directed feature films such as The Goods, starring Jeremy Piven, Inside Amy Schumer, JAY-4:44 Z’s documentary series, an ESPY series of commercials, and numerous nationally coordinated commercials for major brands. He also contributed humor to the 83rd Academy Awards and Seth Meyers’ speech at the 2011 White House Correspondents Dinner.

Early Life

Brennan grew up in a family of ten children near Philadelphia. Brennan has said his father was a tax lawyer who considered himself a joke connoisseur, and his five brothers were all amusing. Brennan says that he first knew he was funny and enjoyed comedy when he was about 8 or 9 years old. He said in an interview that he was already performing prepared material for his classmates in the style of comedians Richard Lewis, Jerry Seinfeld, and David Brenner.

During his high school years, he also watched a lot of comedy on TV, always staying up late to watch Late Night with David Letterman and The Arsenio Hall Show. Also, he had a lot of access to fantastic comics because his brother was a comic. Brennan would sneak into the city on weekends to watch his brother Kevin perform stand-up in New York while he was in high school. Since Brennan was fourteen years old, he hung out with comedians such as Dave Attel, Mike Royce, and Dave Juskow a lot. He got amused by their sense of humor. Those people, especially Juskow, had a huge influence on him.

Later, Brennan shifted to New York and attended NYU’s Film School, but later, he quit. After leaving New York University, he took a job as a doorman at the Boston Comedy Club in Greenwich Village. He would meet comedian Dave Chapelle in the comedy club and pitch jokes to him.

He got 255 dollars a week as a doorman and shared an apartment with comedian Jay Mohr in St. Marks Place.

Co-creating ‘Chappelle’s Show’

In 2002, Chappelle contacted him with a sketch show concept. Brennan was overjoyed since sketch comedy had always been his favorite form of entertainment. After a year, Chappelle’s Show premiered on Comedy Central and became the best-selling DVD series of all time at one point. Eventually, the show became a pop-cultural phenomenon. It was straightforward in its approach to issues such as race, drugs, and sex. 

During the development of the show, Brennan and Chappelle had an excellent working relationship. Brennan said, “Our creative chemistry was pretty explosive. Dave used to say we were like thrill killers. He’d write a joke, I’d go further, he’d go further.”

After being involved in writing and co-producing, Brennan officially conducted and directed sketches such as ‘Charlie Murphy / Rick James,’ ‘The Racial Draft,’ and ‘Charlie Murphy / Prince’ in the show’s second season. 

Two Years later, Chappelle signed a record $55 million two-year contract, but the burden of defending a show that was accused of minstrelsy became too much for him to bear. So one day, Chappelle vanished and fled to South Africa.

Chappelle has spoken about his exit from the show. Chappelle said he felt that the show’s use of dark humor on issues such as race relations backfired on him. On The Oprah Winfrey Show, he appeared and said, “I was doing material that was funny, but was socially irresponsible.” He implied to Oprah that he walked out of the show because he didn’t want to be controlled just as a money-making entity. 

He said: 

I’m partially responsible. You know, a lot of it has to do with me. I’ll give you an example. The first season ends. And in the middle of the seasons, there was a renegotiation. Ultimately, through a series of events and a little pressure, I ended up settling for way less than what I wanted and going forward. And then in season 2, the DVD is released, and it sets all these incredible records-$2.2 million in a week, the largest-selling television DVD of all time. So now suddenly-suddenly, this is a bigger money-maker than they thought. It was already making money. But now, all of a sudden, it’s a whole new revenue stream. And my contract’s up. So we finish the season. So now, you know, the show is gaining popularity. Ratings are up every week. It’s-- I’m the toast of the town. And when the season starts ending, you know, you get the question. So, uh, Dave, uh, what are you gonna do and blah, blah, blah. And I knew to be real tight-lipped about it. You know, it wasn’t like Comedy Central was a hot place to be when I showed up there. You know, so-and then, this the thing we’re having all these arguments…Dave, you got to cut the poop joke. And there was a lot of discussions about what our audience wants. I was like, ah, whatever. And I mean, they were wrong 100% of the time. And the show is an incredibly hard show to do. That’s the other thing. Chappelle Show was- I mean, it’s fun and all these things. But there’s a tremendous amount of work that goes into making a show like that. Yeah… Love is like a nutrient. And I was deficient on vitamin love..I was doing sketches that were funny, but socially irresponsible. I felt like I was deliberately being encouraged, and I was overwhelmed. So it’s like you’re getting flooded with things, and you don’t pay attention to things like your ethics or when you get so overwhelmed. It’s like you had won the lottery…You know, it was like, you got to do everything. So I got all these things. Then I got, you know, your own personal problems that get inflamed when this kind of money comes in. And I got to write a show and do the show. And I was overwhelmed. And it was almost like-- I don’t know. It was almost as if this was happening deliberately…Like, there’s this one sketch that we did that was about this pixie that would appear whenever racist things happens, whenever someone make you feel like they are calling you that N-word, but don’t say it. And it was it was funny. And the premise of the sketch was that every race had this, like, pixie, this, like, racial complex. And-but the pixie was in blackface. Now, blackface is a very difficult image. But the reason I had chosen blackface at the time was because this was gonna to be the visual personification of the N-word. It was it was a good spirit or intention behind it. But what I didn’t consider is how many people watch the show, and how--the way people use television is subjective…I-- finish, because I have a story to tell you. So then when I’m on the set and we’re finally taping the sketch, somebody on the set there one white guy laughed in such a way I know the difference between people laughing with me and people laughing at me. And it was the first time I’d ever gotten a laugh that I was uncomfortable with…And at the same time, I’m just not a naturally assertive person. What was it about the laugh? I know all these people be watching TV, that there’s a lot of people who understand exactly what I’m doing. Then there’s another group of people who are just fans, like the people that-- the kind of people that scream “I’m Rick James,” be at my concerts…I didn’t want-- I got to-- I mean, I don’t want black people to be disappointed in me for putting that out there.…That was the first tipping point....

Brennan learned about Mr. Chappelle’s disappearance while on set. He felt betrayed absolutely. He said in an interview that he would have signed a lifetime contract with Dave because they’d been best friends for 15 years, and he was one of his favorite comedians. “It was painful. It will probably be the biggest personal disappointment of my life,” he said.  

Also, Brennan had an interview with ChicagoNow, in which he elaborately explained that Dave left the show just out of “pressure” and it was unfair for Dave to call him out on Oprah. He said:

I think the thing that was unfair… I think at some point Dave has to talk about it because he has always been very vague about it. My perception, my experience of it, wasn’t Dave’s. We were the golden goose, and Comedy Central was like, 'Do whatever you want, we just need the first episode by (a certain date).' I think the thing that I want to counter would be that somehow I wasn’t a good friend to Dave. I still get Twitter comments about it like, 'Why did you sell Dave out?' I didn’t sell Dave out. We were doing a show, we had the relevant show on television, and he walked out on it without telling me. And so when he comes back, I don’t owe him a phone call. He owes me a phone call, if anything. And also, we don’t even need to talk. It’s like, “What do you want to talk about?” We were friends, clearly that disintegrated in the months leading up to it. When it’s a famous person versus a not famous person, people are going to side with the famous person 100% of the time. If you don’t believe me, ask the O.J. jury. Or the Robert Blake jury, or the Phil Spector jury. They don’t like to think that famous people do human things. My experience was, it wasn’t fair, and then it was extra not fair when Dave went on Oprah and started flagging me as this not good friend. You know, for a black artist that’s beloved to go on TV and say he was victimized by a white corporate structure, that is like white people nectar, it’s like white, liberal nectar, like, “Oh my God, this young black man has been victimized.” Dave did real well from the show, you know. There was a huge benefit to Dave. So the idea that somehow he was victimized…My experience was he wasn’t victimized and that it was a matter of pressure and needing to eject from the pressure. And the fact that somehow I wasn’t a good friend is, you know, garbage. Because first of all, no one knows what the relationship is like, and no one knows what led up to him leaving and what led up to him negotiating and divide and conquer from Comedy Central’s end and all that stuff. Again, no one is ever really going to know my side of it….

Many began to analyze the “white” staff that laughed in the “Pixie” story Chappelle shared on Oprah was none other than Brennan. Later, Brenan related about the particular story and stated that he was arguing with Dave on racial comedy, and it wasn’t a “racial thing.

“The irony of what happened between us, though, is everyone saw it as this racial thing, but it wasn’t. What happened was post-racial. I wasn’t arguing with your black hero, I was arguing with my fucking friend of 15 years. We were arguing about racial comedy, but ultimately, I was arguing with my pain-in-the-ass friend. The way you have a television relationship with him, I have an actual relationship with him. Oprah and Dave made it into this racial thing, and I didn’t see it that way. We were arguing about racial comedy, but we were arguing about a lot of shit. And there are some people who act like you can’t disagree with a black person. It’s like, “No, I do fucking disagree with him.” I was judging him for the content of his character! I was living Dr. King’s dream!” Brennan elaborated.

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