Neal Brennan’s building blocks to comedy success: Be fast. Be funny. Don’t get too famous

“I was writing a joke the other day about the upside of psychopathy and drugs, and I started to think about how Rick James said, ‘Cocaine is a hell of a drug’ to me,” Neal Brennan says, his hands wrapped around a crispy Milanese sandwich. “It’s a meme now. You see it every day even if you don’t know anything about it. But I was actually there. That was the first thing he said to me during that conversation we filmed. It’s so funny and so weird.”

As the “Chappelle’s Show” co-creator tells the story behind arguably the most noteworthy meme from the now-iconic show, the TMZ Celebrity tour bus pulls up right behind him. It’s the tour’s usual Thursday afternoon drive along Melrose Avenue, and Brennan is seated at a corner table on the patio outside Crossroads Kitchen — one of his usual vegan spots.

“I was eating here at one of these tables once, and [the TMZ bus] stopped and asked if I would talk to the bus,” Brennan says, laughing. “I was like, ‘None of those people know who I am.’ I always say I have the NBA referee level of fame. Where people have seen you but they have no idea who you are. Ironically, I ended up in an elevator with somebody who worked in the NBA once, and I was like, ‘Do you work for the Clippers? Are they gonna stay in L.A.?’ And he was like, ‘Yeah, but what’s your name? You’ve come up on my algorithm.’”

But even if Brennan never reaches the levels of fame above Tim Donaghy (barring an FBI investigation), he’s carved out a space for himself in the comedy world that works for him. He’s able to sell out midsize venues around the world with his stand-up, bring a slew of big-name comedians, actors, musicians and more on to his latest podcast, “Blocks,” and still go about doing things in his own way — whether that means breaking down the usual “two guys talking” podcast format into structured chunks about the guests’ emotional weaknesses, having his first Netflix special dive into more trauma and depression than most therapy sessions or turning his most recent special of the same name into an ongoing podcast series.

“I love doing podcasts, but booking them is such an utter humiliation,” Brennan says, his pink button-down backlighted against afternoon traffic. “The plan was to release the ‘Blocks’ special and then people would be banging down the door to get on the podcast — but no one’s ever gonna bang the door down for a podcast. Ever. David Spade once called podcasts ‘jury duty,’ and I guess that’s the right way to think of it. Having said that, Letterman was the first guest, so that helped legitimize it.”

On his Brand New Neal tour (coming to the Wilshire Ebell Theatre on Saturday), the same comedic freedom that let him launch a podcast with a David Letterman interview also means being able to break away from being America’s leading depression comic to focus on more traditional stand-up. Rather than going into the dark depths of emotional shortcomings, Brennan can focus on the bits and jokes that brought him success in the first place — both in the TV/film world and onstage.

“I don’t think I would have succeeded as much without the emo stuff, but the Brand New Neal tour isn’t emo at all,” Brennan says. “I have to make an announcement at the beginning of each show now, because I did a show in Washington, D.C., a couple of months ago and a kid DM’d me after and was like, ‘Dude, I was waiting the whole show for the real you to arrive.’ I wrote back like, ‘So you’re saying I wasn’t sad enough … .’ So now I have to tell people at the beginning of my set that if they need me to be sad, I have some horrible news. Some people might want to see me be sad, but I’m not going to fake it. Ali Wong had a sweet burn on me when I did my ‘Blocks’ special here in L.A. There was a 5:30 show and an 8, but no late show. Ali goes, “You know why that is? Because all your fans are depressed and have to go to sleep early.”

Twenty years after “Chappelle’s Show” premiered on Comedy Central (and 25 after his first collaboration with Chappelle when they co-wrote “Half Baked”), Brennan’s comedy career has extended far beyond Rick James memes and clinical depression. He’s written, directed and acted in both TV shows and movies. Dozens of his TV sketches are now classic cultural moments — particularly as the pendulum of popular comedy swings back toward sketches thanks to the rise of shows like “I Think You Should Leave.” His poignant stand-up hits the highs and lows of modern life, and he’s seemingly incapable of not coming up with new bits for every new topic he comes across.

Comedy has more of a sell-by date nowadays, Neal Brennan says. “In some ways, the YouTube algorithm and the Instagram algorithm are the bookers now.”

(Abigail Keenan)

While constantly churning out new material may seem necessary standard fare for most comics, the biggest difference for Brennan is that he’s both aware of how fast comedy content moves in the algorithm-based internet and perfectly capable of keeping up with that speed. While some of his more famous friends are selling out arenas with the same material they’ve been using for a year or two, Brennan can come up with the jokes of tomorrow while filling theaters virtually anywhere he wants today.

“Comedy now has fewer gatekeepers and an almost infinite amount of gates,” Brennan says. “In some ways, the YouTube algorithm and the Instagram algorithm are the bookers now, but it still favors the same s—. It’s about having a sticky premise and memorable jokes, but you have to be way faster. People in my generation will release specials, and it’s like, ‘Oh, dude, all of these premises were done six months ago … .’’”

If Brennan never wrote, directed or performed comedy again, his legacy would be perfectly secure. As the Keith Richards to Chappelle’s Mick Jagger, even the trolls lurking in YouTube comments are aware of Brennan’s contributions over the years. He’s revered by other comedians for his work new and old, and he’s adapted to the times and rolled with the punches better than many of his contemporaries. He’s done just about everything there is to do in the comedy world before the age of 50 and in recent years has accepted that just because some of his peers are able to sell more tickets or bring in bigger paychecks doesn’t necessarily mean things are any better for them. After all, no one is going to bother wasting time “canceling” him when a lot of people’s only response would be, “Who?”

“The only people who get canceled — and they’re not even totally canceled, but more like ‘reduced’ — were the people who did vaguely illegal sex things,” Brennan says. “No one’s been hindered by their material. Dave and Joe Rogan are both still doing arenas. I know like 12 people who do arenas, which is insane. Cancel culture is just a matter of eyeballs. If you get to be Dave’s size or Joe’s size, there are so many eyeballs on you that someone is going to have a problem with you. You just have to hire more security guards and know that someone’s more likely to heckle you when there’s 16,000 people in an arena.”