My first question for Neal Brennan has almost nothing to do with him, and he’s used to it.
“Oh, let me guess, is it about Dave [Chappelle]?” he playfully asks.
He then fields my query centered around another famous comedian, Bo Burnham, who went on to direct indie flick and likely award winner Eighth Grade after working with Brennan and Chris Rock on the latter’s 2018 Netflix special Tamborine.
“I would say Bo is confident, but I don’t want to make him sound arrogant,” Brennan says. “He’s a know-it-all, and I am too, so it takes one to know one. He has opinions on everything, and that’s what you have to have to be a director. The thing about comedians is we have to do a bunch of jobs. We’re directing [and] writing ourselves, so I’m never surprised when a comedian can do stuff.”
It makes sense that Brennan’s expectation for a comedian mirrors his own do-it-all nature. The NYU film school dropout has done everything from write for tween 90s television shows like Kenan & Kel and All That to directing 2009’s The Goods: Live Hard, Sell Hard produced by Will Ferrell and Adam McKay. Perhaps most famously, he co-created and cowrote Chappelle’s Show, one of the most successful sketch comedy shows ever to air.
“When I was doing NYU, I went to the club at night and worked the door,” Brennan says. “The film kids were the biggest bunch of jerk-offs you would meet in your life. At the club, it was unknown Louis C.K., unknown Dave Chappelle, unknown Sarah Silverman – and that was every night pretty much. I liked those people better and I stayed there.”
In between his foray into onscreen productions, Brennan’s commitment to standup comedy has remained consistent. Despite all his film and television credits, the stage is where his career started – and it’s seemingly what he’s most focused on at the moment. Brennan and his Here We Go tour will stop at the 9:30 Club in early December.
“Standup is really popular, as well it should be,” he says. “The only people being honest are standup [comedians] and the upside is, there’s a lot of eyeballs on them.”
Brennan’s 2017 Netflix special 3 Mics allowed him to intertwine a more dramatic angle onstage for the first time. The format included three segments: punchy one-liners, traditional standup, and a discussion about depression and his relationship with his father.
“While I haven’t done anything strictly dramatic, I bring drama to standup – the place where no one wants it,” he jokes.
On tour now with a new narrative, Brennan declares he’s out of sad stories. With straight standup as his current focal point, he’s found comfort in getting back to writing jokes.
“It’s very premise-based. I’ll sit down and write it out as longform as I can, with as many beats as possible. A lot of times, the thing you think is the joke isn’t.”
With a man who has done so much at such a young age, it’s hard not to ask about the things he hasn’t done yet.
“Why not venture into dramatic filmmaking? Why don’t you have some kind of podcast like other comedians?”
He’s thought about doing those too, he says. For a dramatic film, he needs an idea. For the podcast, he’s working on something with fellow comedian Michelle Wolf.
“No format, just us talking,” Brennan says of his forthcoming podcast. “[Comedians] are very entertaining. We have to do these things, so we’re already opinionated and funny and talkative.”
9:30 Club: 815 V St. NW, DC; 202-265-0930; www.930.com