Neal Brennan on Co-Creating Chappelle's Show and His Half-Baked History with Toronto
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Neal Brennan on Co-Creating Chappelle’s Show and His Half-Baked History with Toronto

The comedian returns to perform several shows as part of Just For Laughs 42, starting tonight.

Detail of a photo courtesy of Just For Laughs.

Neal Brennan
Various times and venues, September 25-28
Festival Passes $99-149

It’s now been over six years since Dave Chappelle put an end to his sketch program Chappelle’s Show at the height of its popularity, escaping the overwhelming fame with a spiritual retreat to Africa. The Comedy Central hit ascended to prominence with incisive skits that rank among the very best of the genre. For co-creator and comedian Neal Brennan—the man responsible for directing the segment that brought us the ubiquitous phrase, “I’m Rick James, bitch!“—he will never tire of fans wanting to talk about it.

“Because I love the show so much and it changed my life,” he reasoned in a phone interview. “I always make the analogy of when an actor says, ‘Don’t call me Billy anymore, call me William.’ It’s always positive, so why would I get sick of it?”

When we asked him what the apex of the show was for him, Brennan cited a memorable night in Cleveland at Prince’s induction into the Rock and Roll Hall of Fame, a week after the Prince episode of the show aired—that night featured gold pyjamas and pancakes, among other highlights. (The incident has been recently immortalized as an animation on sportswriter Bill Simmons’ website, Grantland.)

“It became almost too big,” Brennan said. “It became almost a responsibility.” After the show’s demise, Brennan decided to engage his comedic talents in a number of different capacities. He’s directed films like the Will Ferrell–produced comedy The Goods, written for current Saturday Night Live head writer and Weekend Update anchor Seth Meyers at the 2011 Correspondent’s Dinner in Washington, and regularly performs stand-up. The balance between all of these different projects is important to Brennan.

“Everything in showbiz is such an all-in bet that it’s like, ‘Let me put a bet in over here, let me put a bet in over here, let me put a bet in over here’, and then if something should happen—if Chappelle goes to Africa for instance—I’ve got other pots boiling.” Lest anyone think that sounds as if his motivations are entirely business-related, he is quick to clarify. “I just like being able to do all of this stuff, honestly,” he said. “I’m a good director, so I’d like to direct more. And I also like working with people that I like. I mean, Seth’s like my best friend.”

One of Neal Brennan’s projects, Champs, a podcast focusing on minorities in comedy that he records with fellow comedian and Just For Laughs performer Moshe Kasher, is yet another entry for a format that has developed into a fascinating peek behind the curtain of a world long shrouded in mystery. Brennan sees this as something of a double-edged sword.

“Now I actually think there are too many people talking about comedy,” he said. “but I think it’s given people insight into who’s actually respected. A guy like Carlos Mencia couldn’t get away with stealing jokes anymore. It’s the same thing that happened to comedy in general. The biggest comedy producer right now is Judd Apatow, and he also happens to be one of the best comedy writers. It’s made it more fair.”

While he says that his preparation doesn’t change when performing at a festival like Just For Laughs, Brennan does find the environment different than that of a typical show. “It feels like you’re on vacation with your friends,” he explained. “Like, ‘Hey, where you going? I’m doing a show over here’ and you all stay in the same place, it’s fun.” This is hardly his first time in the city; he was last here for a successful run in July.

“I booked the Laugh Sabbath thing. Those guys got in touch with me via Twitter and I did a couple of shows at the Rivoli and sold out both of them. I like how gratifying it is to be able to say ‘Hey, I’m gonna do a show.’ And then I just go on Twitter and say, ‘Hey, Toronto people, I’m doing a show.’ And then I can sell, you know, 180 tickets just kind of based on that.”

That is a far cry from his experience in 1997 when Brennan came to Toronto to shoot the stoner comedy Half Baked, a movie he co-wrote with its star Chappelle when the two were starting out. Brennan has gone on the record about his disappointment with the results and, given that fact, it’s reassuring to hear that he bears no grudges against where it was filmed.

“Look, I don’t hold it against Toronto at all. And as much as I sort of poo-poo Half Baked, I was 23 and it was a good time,” he recalled. “Who can forget The Brass Rail? I have no quarrel with the city of Toronto.”