“I was writing a joke the other day about the benefits of psychopathy and drugs, and I started thinking about how Rick James said, ‘Cocaine is one hell of a drug for me,'” says Neal Brennan, his hands wrapped around a crunchy 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 the conversation that we filmed. It’s so funny and so weird.”
As “Chapelle’s Show” As co-creator tells the story behind arguably the most notable 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 down Melrose Avenue, and Brennan is seated at a corner table on the patio in front of Crossroads Kitchen — one of his usual vegan spots.
“I ate here at one of these tables once and [the TMZ bus] “I stopped and asked if I could talk to the bus,” Brennan says, laughing. “I thought, ‘None of these people know who I am.’ I always say I have NBA umpire fame. Where people have seen you but have no idea who you are. Ironically, I ended up in the elevator with someone who had once worked in the NBA and I was like, ‘Do you work for the Clippers? Will they stay in LA?’ And he said, ‘Yeah, but what’s your name?’ You hit my algorithm.’”
But while Brennan never achieves the level of fame that Tim Donaghy surpasses (barring an FBI investigation), he’s carved a place in the comedy world that suits him. He’s able to fill medium-sized venues around the world with his standup performance, bring in a crowd of big-name comedians, actors, musicians and more into his latest podcast, Blocks, and still do things his own way – whether it’s breaking down the standard Two Boys Talking podcast format into structured sections on guests’ emotional vulnerabilities, immersing his first Netflix special in more trauma and depression than most therapy sessions, or is adapting its latest special of the same name into an ongoing podcast series.
“I love doing podcasts, but booking them is an absolute humiliation,” says Brennan, his pink button-down shirt backlit against the afternoon traffic. “The plan was to do the ‘Blocks’ special and then people would smash the door to get on the podcast — but no one will ever smash the door for a podcast. Always. David Spade once called podcasts “jury duty,” and I think that’s the right way of looking at it. However, Letterman was the first guest, which added to the legitimacy.”
On his brand new Neal On tour (coming to the Wilshire Ebell Theater on Saturday), the same comedic freedom that has allowed him to start a podcast featuring an interview with David Letterman also means he can break away from America’s leading depression comedian and focus on more traditional stand-up comedians. Rather than delving into the dark depths of emotional imperfections, Brennan is able to focus on the little things and jokes that have made him successful in the first place – both in the TV/movie world and on stage.
“I don’t think I would have had as much success without the emo stuff, but without the brand new Neal “Tour isn’t emo at all,” says Brennan. “I have to make an announcement at the start of every show now because I did a show in Washington, DC a few months ago and a kid DMed me afterward and said, ‘Dude, I’ve been waiting the whole show for you to be real.’ I wrote back, “So you’re saying I wasn’t sad enough…” Now I have to tell people at the start of my set that I have terrible news if they need me to be sad. Some people might want to see me sad, but I won’t fake it. Ali Wong had a sweet tooth on me while I was doing my “Blocks” special here in LA. There was a 5:30 show and an 8:00 show but no late show. Ali says, “Do you know why that is? Because all your fans are depressed and have to go to bed early.”
Twenty years after the premiere of “Chappelle’s Show” on Comedy Central (and 25 years after his first collaboration with Chappelle when they co-wrote “Half Baked”), Brennan’s comedy career stretches well beyond Rick James memes and clinical depression. He has written, directed and starred in both TV shows and films. Dozens of his TV skits are now classic cultural moments — especially as the popular comedy pendulum is swinging back towards skits thanks to the rise of shows like I Think You Should Leave. His poignant performance reveals the ups and downs of modern life that he seems incapable of not He comes up with new parts for every new topic he comes across.
While the constant production of new material seems like a necessary given for most comics, the biggest difference for Brennan is that he both knows how fast comedy content moves on the algorithm-based internet and is perfectly capable of keeping up with that speed. While some of his better-known friends are selling out the same footage they’ve been using for a year or two, Brennan can come up with tomorrow’s jokes while still filling theaters pretty much anywhere he wants.
“Comedy now has fewer gatekeepers and an almost infinite number of gates,” says Brennan. “In a way, the YouTube algorithm and the Instagram algorithm are now the bookers, but they still prefer the same S-. It’s about a sticky premise and catchy jokes, but you have to be a lot quicker. People of my generation are going to put out specials and be like, ‘Oh dude, all these premises were completed six months ago…’”
If Brennan never wrote, directed, or performed in comedy again, his legacy would be perfectly secure. As Chappelle’s Keith Richards and Mick Jagger, even the trolls lurking in YouTube comments are well aware of Brennan’s contributions over the years. Revered by fellow comedians for his work new and old, he has adapted with the times and handled the hits better than many of his contemporaries. He did just about anything there is to do in the comedy world before he turned 50, and over the past few years has come to accept that just because some of his peers can sell more tickets or rake in bigger paychecks, it doesn’t necessarily mean it’s better off. After all, no one is going to bother wasting their time “cancelling” him if the only response from a lot of people was “Who?”
“The only people that get cut — not even completely, but more like ‘reduced’ — were the people who were doing vaguely illegal sex stuff,” says Brennan. “Nobody was handicapped by their material. Dave and Joe Rogan both still play arenas. I know about 12 people who play arenas, which is crazy. Cancel culture is just a matter of eyes. If you’re the size of Dave or Joe, you’ll get so many looks that someone will have a problem with you. You just have to hire more security and realize that when there are 16,000 people in an arena, there is a greater chance that someone will harass you.”