Brennan Writes Chappelle Laughs

By Steve Hintz
Irish American Post New York Bureau

Neal Brennan is a monster. A hulk of unadulterated comedy. Half of the outrageous creators of the hit Dave Chappelle television show. Brennan, at 30, is one of today’s foremost contemporary comedic writers, albeit one with a deliciously Irish twisting of humor.

The dude is cool, too. I sat up with him on St. Patrick’s Day and discussed comedy, celebrity status, being Irish and working with one of the hottest, most outrageously enlightening acts of the current entertainment scene. 

Brennan’s office is sparse, with only a simple desk, bookshelf, couch and a couple of chairs. A storyboard for the Chappelle show hangs above this young guy. There are with huge gaps on the planner where later sketches will be penned. Although shooting for the last show of the season is coming up, the writers still haven’t come up with the concepts.

Unfazed, Brennan leans back in his swivel chair.

I almost expect him to kick up his limbs on the desk and drag on a smoky Swisher Sweet. Brennan’s Outkast tee-shirt, baggy jeans and oversize wintery coat make him look like he’d be more comfortable out on the block than in this stuffy room. But it’s exactly where he wants to be. 

Hey, Brennan is the king of this block. Phone calls pour in and out from the likes of Mike D of Beastie Boy fame. Eager management tries to snare prestigious guest appearances for their clients and a young staff jets back and forth running errands.

Despite the frenzy, Brennan’s very approachable. I almost feel like we’ve hung out  together before.

Brennan attended the prestigious NYU Film school for a year after graduating from a working class Catholic high school in the suburbs of Philadelphia. His collegiate stay would be short, however. His street-smart sense of humor and modest upbringing didn’t jive with the upper echelon attitude of the other students at the prestigious institution.

Comedy was calling and it wasn’t long before Brennan found a job handing out flyers at the Boston Comedy Club in NYC’s Greenwich Village. Although struggling at the lowest rungs of the comedy chain, he was finally immersing himself in his element. This is when he met a young comic in need of a critical ear, Mr. Dave Chappelle. Chappelle was a young relatively unknown comic, making the rounds in New York’s comic underground.

"I pitched him some improvements on his jokes," Brennan repeats. Before long, the two were "boyz." The friendship seemed predestined, because the writer’s career finally started to show some life. He got his first break at a skit writer on the MTV show, Comikaze. At 19 years old, Brennan was living the life. 

A year later, Brennan moved to L.A. to work on the pilot for Singled Out, starring the young Jennifer McCarthy. But he wasn’t comfortable in California. "I began to feel like I was always waiting for my friends from New York to come out and visit," Brennan laments, his hands behind his head.

"I was still very inexperienced in dealing with the entertainment establishment and didn’t play the game very well," Brennan admits. "I didn’t know how to deal with the industry until I was 25."

"When I was younger, I used to take everything so personally. And I was a junkie for showbiz rushes...meeting famous people, going to parties, ego boosts...I just had no relationship with myself until around age 25."

The next couple of years found Brennan working on a show for Nickelodeon called All That, a project for which he credits gaining writing discipline. "They really showed me the business of writing and the importance of discipline," Brennan remembers.

In 1996, Brennan snared a pitch meeting with producer Bob Simonds. "Bob Simonds is a film producer...he's produced, Cheaper By the Dozen, Happy Gilmore, The Wedding Singer and about 20 other movies. I got a meeting with him because a friend of a friend worked for him and read a script of mine (don't remember much about it.) She didn't like the script much, but took a meeting with me as a favor, and we got along, so then I got to meet with Bob."

Although his film script didn’t get picked up, Simonds liked Brennan and encouraged him to keep working at his writing.

A couple of weeks later, Chappelle called and told Brennan that he had just met with a producer. "Dave told me that if the guy calls, tell him we’re working on the script for a weed movie," Brennan chuckles. It turns out "the guy" was Simonds and the writing duo was in.

The team had a month to come up with a premise for a spur-of-the-moment pitch for a film centered around marijuana. Not inspired until the night before the deadline, the two threw together ideas for cult classic Half Baked. Subsequently, the two 23-year-olds landed their first movie deal.

"It was really fuckin’ incredible. We were there for every take of the film," says Brennan. The two guys did, however, learn a great deal about the Hollywood machine. Without much creative control of their piece, the "real film" that they had envisioned "ended up being a cartoon," indicates an exasperated Brennan, rolling his eyes when recalling their efforts. 

Yet Chappelle’s performance made the movie, according to critics.

Subsequently, the two earned their first writing credits for a major motion picture, a feat few such tyro screenwriters can brag about. The duo solidified their relationship, allowing the Chappelle/Brennan ship to set sail on a voyage that started in a small Boston comedy club almost four years earlier. 

The writing for Chappelle’s Show season starts in July. According to Brennan, "There is no rhyme or reason" how the two come up with the outrageous sketches that have made their show a must-see for the hip-hop generation. 

"We’re the first fans of our sketches," Brennan admits. They almost come from somewhere else, like gifts." When deadlines crunch, which is every day, they enforce a little forced Buddhism. "Be in the moment and write …some of my best work was done at the last minute in school," he says. Sixteen hour workdays are fun but grueling. Brennan admits giving up a personal life in pursuit of his career. But for all The Irish American Post’s lovely lady readers out there, Brennan is currently single and residing in New York City. 

"There are currently no women on the hook. I guess at this point I'm looking for a woman who gives me a lot of freedom and time to myself without taking it personally. I'm a bit of a loner. Truth be told, I'm not looking all that hard. Just busy working, taking advantage of the current professional opportunities.

"Right now, I'm renting this furnished one bedroom near Central Park. It's super granny style. The decor is awful. And I never got the Park. I didn't move to New York for the nature," he admits.

F.Y.I. to the ladies…The way to Brennan’s heart is through apple pie ala-mode. "I’d rather throw an apple pie party then go to the club sometimes," he proclaims.

As we spoke, St. Patrick’s Day revelers filed into bars around the Big Apple and Brennan groans that there would be no celebrating on this typical work day. Yet he’s Irish to the heart and has been to the Emerald Isle a couple of times, first visiting Ireland as a child with his family and again to Dublin. 

"I've been to Ireland twice in my life...once when I was about 8 years old...I remember my grandmother who lived there (in Castleisland, Co. Kerry) would always try to get my dad to stop so she could buy all us kids sweets. And my dad would snap, "Oh, Jesus, they just had candy, Mary. Give it a rest." I went there a couple years ago for about a day-and-a-half. It was kind of cold and everybody looked like me. It made me a little crazy, so I went to London. More of the same."

Chappelle often teases Brennan about his Irish heritage. Paraphrasing an Irish quote, his pal tells him, "May the Lord have work for your hands."

The joke calls to the heart of what the two find funny about everyday experiences and the subtle nature of comedy. Like in any good Irish home, there is a fair share of comedic sensibilities. Brennan’s brother Kevin, one of 10 from this Irish Catholic family from the Chicago area, has written for Saturday Night Live and is close friends with comic Dave Attell of Insomniac MTV fame and Ray Romano from Everybody Loves Raymond. "It was really cool having these guys around…a real in to the comedy scene."

Brennan has his summers free and started doing stand-up about a year. "I did it once in 1992 and was horrible. Then I did it again in 1997 and it went pretty well, but then we ended up doing Half Baked after that. I didn't do it again until 2002. A couple of months later, we did the pilot for Chappelle's Show. I can't explain it, but I do it as a last resort. Whenever I'm not happy with how my career is going, I do it, and then coincidentally, my career picks up. What's nice about it is, you can prove that you're funny without a lot of red tape. Just walk onto the stage and speak into the microphone. It's a good feeling when things aren't going your way career-wise. Confirmation that you're not crazy," Brennan says. 

Asked about the difference between writing comedy and performing comedy, Brennan explains that "writing for comedy is like detonating a bomb and watching it go off in the distance. Stand-up is when the bomb detonates on you."

Although he enjoys the challenges of performing, Brennan admits that his natural gifts lie more in directing and writing. "Dave is a natural actor and I’d be disrespectful to put myself in the same category with him. I’d be happy to direct Dave the rest of my life," says Brennan. As for the future, Brennan wants to continue the directing, although he admits he’s "a pretty big pain in the ass." 

"I think I can just be a pain in the ass when I work on the show in any capacity. I'm a bigger pain in the ass when I'm not directing, because I have to look over the director's shoulder and make sure they're getting what Dave and I want. I'm sure it's a pain for them. 

How do you know, I asked him. "Because they've told me. When I'm directing the stuff myself, I know exactly what Dave and I want. We wrote it. We've talked about it. We almost always want the same thing. It cuts out the middle-man so to speak. But I like the directors we use and they always add stuff to the material in one way or another."

He says his favorite films are by "anybody who writes and directs their own stuff. I even liked Seabiscuit." 

The duo’s claim to fame, according to Brennan, is that they "do their show on Planet Earth." The sketches originate from talking about issues on the lips of most of the hip-hop generation, both white and black between the ages of 18 and early 30s. Brennan insists that viewers often interpret too much from the show at times. When there’s talk of "white people," Chappelle and Brennan refer to the corporate milieu and the powers-that-be. 

""In reality," Brennan asserts, "we’re equal opportunity comedians with blacks, Hispanic and Asians all receiving their fair share of the comedic milkshake.

A recent sketch for the show outlined a race draft, in which culturally ambiguous icons were "drafted" by representatives from different groups.

"Dave is not a racist," Brennan counters, rather he is "the biggest representation of a human being." Much of the appeal of the show is the full range of personality that is on display when Chappelle acts. Brennan insists this is what he calls "rare" in television, which often tries to caricature a person. "In our show, freedom becomes the message," Brennan continues. 

"Dave is just about as talented a guy as you could be. He can act, write, produce, direct, do stand-up, and is also really adept handling all the corporate stuff that goes along with it. The thing about Dave that not a lot of people know is he has a bunch of songs on his tunes library that are like a cappella versions of classical music. So we'll be writing a sketch about crack or racism or sex, and Mozart's Canon in D Minor as sung by a choral group will be playing in the background. He's just a really hilarious, surprising, multi-talented, multi-faceted person. And we still get along after all these years."

The Dave Chappelle Show is an anomaly. The fact that these two dynamic men — one white and one black — understand their complex nature as humans in relation to the country’s cultural and racial experience has created truly freeing comedy. Their friendship is grounded in truth, Brennan says, allowing them to explore sticky cultural situations in a safe place. This space is only a small part of their friendship, a relationship which involves many similarities in musical tastes, philosophical beliefs and — most important to their audience — comic sensibilities.

"The show is something Dave and I put our blood, sweat, and tears into and are very proud of. It comes out of a friendship and creative chemistry that I think we're both grateful for."

Of course, Brennan’s been blessed with talent. Combine that with the creativity of a close buddy and it’s obvious that the pair has the whole world of entertainment by the neck.

Chappelle’s Irish blessing for his good friend Brennan has paid off. The Lord has presented more than enough work for his hands.