Neal Brennan Longs for Connection

Last fall, at the Cherry Lane Theatre, the comedian Neal Brennan performed a one-man show about his own alienation, much of it self-imposed. He wore fashionable sneakers, glasses with clear frames, a lapel mike, and a button-down shirt buttoned all the way to the top. “I’m clearly liberal,” he said, a few minutes into the ninety-minute show. “Look at me. Bone-thin.” He paused for laughter—a bit more of it than he seemed entirely comfortable with. “But I don’t feel like part of the group, because liberals are the least welcoming people on the planet. You can believe the right shit, but if you don’t express it the right way. . . .” He trailed off, as if searching for an example. “You ever try to talk about transgender issues in public?” A palpably tense silence filled the room. “See, even right now, you’re, like, ‘We don’t gotta do this, Neal.’ ” And, surprisingly, he didn’t. He turned the joke into a meta-joke, leaning, like any good liberal, on his own guilt and ambivalence. And then he moved on.

A version of the one-man show, trimmed to an hour and directed by the genre-transcending magician Derek DelGaudio, was just released as a Netflix special called “Blocks.” The name might be a play on the language of therapeutic self-diagnosis (as in “mental block”), but it also refers, more literally, to the show’s basic conceit. Brennan stands before a wall of toy-like blocks, which represent “the areas of my life that make me feel like something’s wrong with me,” and turns them over in his hands, using them as prompts for various bits: money, Twitter, gun control, Kanye West. “People are, like, ‘That guy’s fucking crazy,’ ” Brennan says in the special, which was filmed when West was an erratic Trumpist but not yet an open anti-Semite. “He’s a rapper. Since when do you rely on rappers for their emotional stability?”

In the Netflix special, the meta-joke about “transgender issues” remains mostly unchanged, except that, after “We don’t gotta do this, Neal,” Brennan adds a new tag: “Don’t go out like your boy.” This is an allusion to Dave Chappelle, who became Brennan’s friend and writing partner thirty years ago, when they were both nineteen. Together, they wrote the cult-classic stoner movie “Half Baked,” in 1997; a few years later, they co-created “Chappelle’s Show,” the sketch program that still serves as a touchstone for a generation. “That’ll probably be the top thing on my résumé forever, for better or worse,” Brennan told me. “I’m proud of some of what I’ve done since, but, to this day, ‘co-creator of “Chappelle’s Show” ’ is the thing that someone can say about me and everyone else in the room will go, ‘Okay, no further questions.’ ” One of the highlights of “Blocks” is a bravura humblebrag: a set piece about a time when Brennan was invited to a Netflix party along with Eddie Murphy, Ellen DeGeneres, Chris Rock, and about a dozen other comedy A-listers, and how being in that room both boosted and gutted his confidence.

Brennan and I spoke at a café in the West Village, and then again in October, over the phone, when he was back home in West Hollywood. At one point, our phone connection cut out, and he called me back over FaceTime. In my experience, most people have an easier time being candid when the visual component of a call is stripped away; with Brennan, who has spent thousands of hours divulging his secrets to strangers, FaceTime seemed to make him, if anything, even more unguarded. Our conversations have been edited for length and clarity.

Let’s start with Kanye. Obviously, you’ve been doing this show for a long time, and you did not plan to release it around a Kanye news peg.

Certain things you fear are going to go out of fashion, or out of the news cycle, but Kanye is sort of evergreen. To me, he’s the biggest—if not the biggest cultural contributor in the last twenty years, then one of the biggest. My basic idea was about how liberals digested him: they loved it when he was against George W. Bush, but once he was for Trump then it was like, “Can you shut the fuck up?” Obviously, it has since gotten way darker than that. I mean, it’s like the YouTube or Facebook algorithm came to life within him. I think he wanted freedom as a Black man to express something other than the boilerplate, prescribed point of view. And now he’s way outside the box. The thing is: the good thing about boxes is that they can contain things. And when you’re that far outside the box, your shit’s all over the street. It’s sad, but he is almost a perfect object lesson, or metaphor, for our last fifteen to twenty years.

When you said “our last fifteen to twenty years,” I thought at first that you meant the last fifteen to twenty years that we have left as a species.

[Laughs.] Also maybe that.

O.K., well, if he’s an object lesson, then what do we take from it?

That I don’t think we can handle all this exposure. I don’t think human beings can take this much exposure to information, and this much exposing of our own information. The ingoing and the outgoing. I told somebody, “In some ways, I’m glad Beethoven’s dead, so that I don’t have to wake up to Beethoven saying that QAnon had some good ideas.”

I don’t know. I really think social media plus COVID was too much. We got overpowered. All the information that we’re all ingesting all the time—it just overwhelms us.

In your own act, how do you know when to listen to your own inner voice, even if it’s contrary to the herd, and when to step back and go, Oh, I’m way off here? And just to be clear: you don’t have a bit in your act where you talk about how the Jews control the media and run the world.

[Laughs.] I mean, it’s silent. But it’s in there.

[Laughs.] But do you have any version of that, where you feel like you’re getting close to a third rail, or where you’re feeling the audience get nervous or pull away from you? How can you tell the difference between “I’m charting new territory” and “I’m off base and I will regret this later”?

With racial stuff, I have a good jury of people who will watch and respond.

Do you have an example of a racial joke that you cut because the jury wasn’t into it?

Yeah, the Black-church thing. [In the stage version of the show, but not in the Netflix special, there was a bit comparing “Black church” with “white church.”] I cut it for two reasons. One of them is just, like, comedy level of difficulty. I wouldn’t be the first person to say that Black church is different from white church. And the other is that the person who told me to cut it is a comedy icon.

This is one of those situations—is it more awkward to drop the name or not drop the name?

I mean . . . Chris [Rock] told me to cut it. There was one line in it that Ezra Edelman [the director of the documentary “O.J.: Made in America”] told me to cut a year ago, and I did. And then Rock saw it and was, like, “Nah, just cut the whole thing.”

Because he didn’t think it was funny enough?

It was just a little . . . this is where you get into, like, “I know it when I see it.” I couldn’t even tell you exactly why. It’s sort of like “The Blues Brothers.” That scene where they go into the Black church—I mean, it’s basically blackface, right? You don’t know that as a kid. You just think they’re cool and weird.

What about your jokes about gender? Do you have a jury of your peers for that too?

Is there a Chris and Dave equivalent, you mean?

Yeah, do you have, like, Ali Wong and Amy Schumer and—

No, but I know they’re gonna see it. And I don’t want Ali or Schumer or any of these people to think I’m a hack, or to think I’m, like, a bigot against women. I don’t want them to think that I’m a worse sexist than they are.

It’s hard to make comedy that doesn’t have a shelf life, particularly when you’re pressing on potentially third-rail stuff. I assume you don’t want to look back at something you’ve made and find that it aged badly, the way you’re talking about with “The Blues Brothers.” So how do you try to account for that in the present, thinking about what it might look like in the future?

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