Neal Brennan tells Jalen Rose about failing with Dave Chappelle

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Comedian Neal Brennan is the co-creator of “Chappelle’s Show” and frequent collaborator with the all-time great comedian (who, in case you’ve been living under a rock, has been in the news lately with his Netflix special). Neal’s also a writer, director and stand-up with a one-man off-Broadway show called “Neal Brennan: Unacceptable.” An impressive résumé can’t keep you from bombing in comedy, but a good sense of humor can inoculate you from taking yourself too seriously.

On this week’s “Renaissance Man,” he revealed the real-life perils of having an off night onstage and his roll-with-the-punches attitude.

“I was almost dating a woman,” he told me. “We were kind of circling dating. She came to the show [and] I bombed. Haven’t heard from her. Swear to God … The woman actually said to me after the show, ‘How do you think it went?’ … There’s only a few things people say when you bomb, and that’s one of them.”

In his Cherry Lane Theatre show, he explores his inability to neatly fit into any group. He noted that he is 48, single, doesn’t eat meat, drink much, doesn’t smoke weed. He doesn’t have any kids.

I’m no psychologist. I’m just a fan of Chappelle and Neal. But I would say maybe he just wants some peace and quiet. After all, he is the youngest of 10 siblings. That’s right, 10. And I made him recite their names, which came out fast, like he was channeling the Micro Machine man.

“I think 10 kids, it should be said, is too many … I’m living proof. Like, if you’re thinking about it, don’t do it … I do a joke in the show that my parents were born during the Great Depression, and they were nice enough to bring it with them,” he said.

However, he said, his siblings all had pretty cool jobs growing up and they opened their worlds to him. One was an usher at the stadiums and arenas in Chicago, which enabled him to go to a lot of Cubs and Bulls games.

“This is how long ago I used to go to Bulls games,” he told me. “I saw a little white girl mistake Michael Jordan for Orlando Woolridge.”

One brother was a caddie on the PGA tour and another, Kevin, was a comedian, which was very consequential for him.

“We moved to Philly when I was in eighth grade … Then I used to come up to New York on the weekends and my brother was just starting. An average show when I was in high school … was like Ray Romano, Jon Stewart. Then [when] I came here for college, Dave Chappelle, Chris Rock were around.”

He went to NYU film school because he admired Spike Lee, but he dropped out after a year. He said he and Chappelle became close and realized they were “kindred spirits,” creating a partnership that gave us the 1998 cult stoner classic “Half Baked.” That movie is an all-time favorite, but my highbrow opinion on this piece of cinematic art didn’t have any sway over audiences: It was a commercial flop. But Neal explained that their opening weekend was like playing against the Bulls in the ’90s.

Neal Brennan speaks onstage at The Art of Elysium in 2018.
Neal Brennan onstage at The Art of Elysium in 2018.
Getty Images for The Art of Elys

Its competition at the multiplex included “As Good as It Gets,” “Good Will Hunting” and “Titanic” — a movie I still haven’t seen, but I’ve heard people liked it.

The poor box office numbers made things a little awkward for Neal and Chappelle, and they took a hiatus from each other.

“When you have a failure, you kind of don’t f–k with each other for a little bit. There’s a stink to it,” said Neal.

But it fueled the creation of the greatest comedy sketch show off all time. When the pair reunited, they were ready to make pop culture history.

“‘Chappelle’s Show’ was a direct response to ‘Half Baked,’” said Neal.

“A lot of the decisions about ‘Half Baked’ were made without us. They bring us in and go, ‘All right, so we’re shooting tomorrow,’ and it was too late for us to say anything,” Neal explained. “So on ‘Chappelle’s Show,’ it was like, ‘Hey, every inch, every stitch of fabric, every single decision, every staff member, every machine, every one of us has to approve it’ … It is laborious and it is a pain in the ass, and it’s kind of the only way to make a good thing. Jerry Seinfeld is a billionaire, and the reason his show ‘Comedians in Cars Getting Coffee‘ is good is because a billionaire watches every frame of every shot.”

And no one can argue that their control produced hall-of-fame greatness. My favorite sketch is “The Racial Draft.” Neal said his are the Rick James ones and “Celebrity Trial Jury Selection,” where Dave is up for jury duty in some high-profile trials like Michael Jackson’s and R. Kelly’s.

We talked about the difference between writing for black and white audiences. Neal, who joked that he’s like Eminem because he’s always with black people, said his opinions sometimes get him into trouble with African American journalists. His quick summary: The material has to be more “visceral” and less cutesy for black audiences.

He also waxed poetic about his love of hip hop, especially Kanye West, whom “Chappelle’s Show” championed early on. He also loves DaBaby and hopes he has a comeback. But now he’s going through an “odd spiritual period,” and his music taste is veering into a different territory.

“There’s a plant medicine called ayahuasca,” Neal said. “Will Smith told me about it … I literally can talk about it for 10 hours … It literally put me in touch with God. Will said it’s the most spiritually free experience he has ever had. So I’ve been listening to a playlist on YouTube Music called ‘The Outer Limits.’ It’s all very odd and very experimental, and it will make you feel like you’re tripping a little bit.”

One thing that struck me is that he’s battled imposter syndrome. He said he’s swatted it with a “Shoot your shot” attitude. Neal learned the hard way by having an idea but holding back on saying it. “And then 10 minutes later,” he said, “somebody else would pitch it and it would get bought. I’d be like, ‘See? You have to pitch your thing.’”

And that’s regardless of the consequences.

“It sometimes bombs and girls don’t want to date you,” he joked.

But I have to say, it’s that woman’s loss. And ladies, if you want a funny, funny dude with a lot of heart, Neal Brennan is single.

Detroit native Jalen Rose is a member of the University of Michigan’s iconoclastic Fab Five, who shook up the college hoops world in the early ’90s. He played 13 seasons in the NBA, before transitioning into a media personality. Rose is currently an analyst for “NBA Countdown” and “Get Up,” and co-host of “Jalen & Jacoby.” He executive produced “The Fab Five” for ESPN’s “30 for 30” series, is the author of the best-selling book, “Got To Give the People What They Want,” a fashion tastemaker, and co-founded the Jalen Rose Leadership Academy, a public charter school in his hometown.

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