Neal Brennan Is Done Being Sad

Lacey Rose
·11 min read

Neal Brennan begins his forthcoming Netflix special with a disclaimer of sorts.

“If you’re watching this because you saw my other Netflix specials and I talked about having depression and you wanted to support a fellow traveler, I have some terrible news,” he says at the top of his new hour, “I feel pretty great.”

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Then, rather than linger on his own mental health journey, which he explored in previous critically acclaimed specials 3 Mics and Blocks, he spends a healthy portion of Crazy Good joking about the perks or upside of “bad mental health.” Doing anything else with his latest set, which will premiere on Netflix April 9, felt disingenuous to Brennan, who broke out as the co-creator of Chappelle’s Show in the early ’00s and has segued, more recently, from comic whisperer to comic star.

Over Zoom in mid-March, Brennan opened up about that mental health arc of his as well as the perplexing expectations surrounding the modern-day stand-up and why he’s gotten more comfortable in the spotlight.

Before I got a chance to screen your new special, I found this thread on Reddit where people who had gone to see your set were weighing in. I’ll start by telling you that they were very positive—

I’m still sort of like—

Where is this going?

Yeah. I’m like, uh-oh. (Laughs.)

No, no. I bring it up only because I was struck by this one commenter, who wrote, “His material was outstanding, probably the best I’ve seen him do. I’m really curious how it translates to a special and how his fanbase reacts. Because some people definitely see him as ‘that mental health guy.’ ” It’s an idea that you play with right at the top of the special.

And I’ll tell you why I play with it. I did the show in Washington, D.C. last summer and I didn’t have a rejoinder at the beginning. I just came out and started talking and a guy DM-ed me after and said, “I brought my girlfriend. It was my birthday. We bought tickets for the front row, and I just kept waiting for you to show up.”

Oh, fascinating.

And I knew it was going to happen. Something like that. I always want to do a bit about the kind of heckles I get, which are like, “Be sadder!” So, I put that thing at the beginning, like, “If you want me to be sad, I’m sorry, I’m not sad,” and that sort of covered it. And weirdly, it made the whole show better. It was a good note from the guy.

Before you ever got on stage with this new set, did you have these kinds of conversations about what would be, in many ways, a major pivot, and how it might land?

Yeah. But I’d been feeling pretty good for a couple years to the point where when I did Blocks [his last Netflix special], I kind of had to tap into that old feeling. So, this was a new feeling of optimism — or at least, like, an accepting that bad mental health can be good or what we consider bad mental health has propelled most of civilization. Of course, you could also argue that as my mental health got better, my comedy got better, so I’m saying one thing and maybe exhibiting another. But I wasn’t going to pretend to be sad when I wasn’t.

So, what did you want to say with this special?

Well, definitely the thing about how bad mental health has kind of been the main economic driver of civilization for the last couple thousand years. Most great things are from psychopaths and drug addicts. Basically, [the special’s] in defense of bad mental health or at least [explores] the upsides of it. And I’m not saying, like, don’t go to therapy. I’m just saying that I don’t want certain people to have a good work-life balance. I don’t want, like, the head of Homeland Security to take up photography or poetry, you know what I mean? Do your job all the time. Be obsessed with it. (Laughs.) And I’m going to start thanking people for their insanity instead of castigating them for it because I benefit from it. I’ll stay as far away from you as possible until you come up with the material or the athletic prowess or the invention or whatever it is — I’m definitely going to keep my distance until then, but I’m also going to sign up for your mailing list so I know when new stuff is coming.

You also explore the role of comics in today’s culture.

Yes, the other big thing is this idea about who our cultural and civilizational leaders are now, and how it feels like it’s comedians because everybody else has completely failed or is obviously lying. Religion, corrupt. Religious organizations, corrupt. Political leaders, corrupt. Corporate leaders, corrupt. Civic leaders, media — everybody’s in somebody’s pocket, and it seems like comedians are the only ones incentivized to be honest. But then there’s this weird thing because we’re now the moral leaders, which is, like, what?! I almost called the special, “What do the clowns think?” Why is it up to Dave [Chappelle] and [Joe] Rogan and Ellen [DeGeneres] and Kevin [Hart] and Shane Gillis and Andrew Schulz? Why are these people now moral leaders when that’s not the job. I understand how we got here, but I think it’s a silly expectation.

Does that silly expectation impact the way that you approach your own comedy? As in, are you walking on eggshells that perhaps didn’t use to exist?

Well, I’m in this weird place where I’m not famous enough to get substantially canceled — like, I am not going to get a job and lose it like Shane [did with Saturday Night Live], which, again, then became his propulsion. To quote Bill Burr, “What are they going to do? Take away my podcast?” [Brennan hosts the Blocks podcast.] And Bill’s another one. Like, Bill said whatever, or Kevin Hart, in his monologue, said that moms aren’t fun! Huh?! Supreme Court justice Clarence Thomas takes bribes! Why are you worried about what Kevin said in his monologue or what Bill said about whatever? Or Jon Stewart’s not allowed to say that Biden’s old! Do you not understand what comedy is? I think people think you need to do a funny version of their point of view and it’s like, that’s not my job!

One could argue that it’s become a much riskier job, being a comic.

Yeah, it is risky. But whenever people talk about Dave or Joe being canceled, I just think, “They’re doing arenas.” So, where’s the cancellation? Shane just did The Chicago Theater five times, that’s 18,000 tickets. This thing about being canceled, you’re basically just getting free promo. And again, these megaphones are getting so big that if you’re on Netflix, you’re in 220 million households or something, you’re going to get some blowback. I mean, I have jokes in this special that I’d be shocked if I didn’t get blowback. I have a rape joke.

Does the prospect of that excite you on some level? You kept it in, so I guess I wonder if the pendulum has swung to the point where there’s some degree of thrill in that now?

Thrill would imply that it’s intentional, and that I know what the outcome is going to be. The thing that generally happens is you get blowback for the thing that you didn’t think you were going to get blowback for. So, I do worry about it, but I also think that they’ll only give blowback to people that they think will get hits, so then they have to make this calculation: “Well, is Neal high-profile enough to get hits if I attack him?” And they could make a case either way.

I’m curious, where did you film the special, and how did you make that decision?

At The Fonda [Theatre in Hollywood]. But I’ve never really understood the thing about audiences in general. My audiences are 95 percent the same, wherever I go, even in, like, London or Thailand. The jokes either work or they don’t.

And that remained so despite the fact that this set featured a different kind of material and a different version of you?

Yeah. And what I’m hoping for [the special] is that people that thought I was mopey or maudlin or self-pitying and maybe had written me off before give me a chance. It’s a hard thing to ask of people. Like, “No, no, no, we’ve reimagined who Neal Brennan is.” But hopefully if you watch the first 11 or 12 minutes, you’ll see, “Oh, he’s just being reckless and funny. He’s not being contemplative in any way.”

You also chose to direct the hour yourself. How come?

Because I end up always sort of ball hogging. Derek DelGaudio directed the last one but then I ended up doing another pass on the edit and why put somebody through that?

I noticed Bill Burr is an executive producer, and I was curious about his contribution.

Bill Burr and Al Madrigal have this company, All Things Comedy, that produced it. They’re great and very pro comedian — and not like there’s a ton of graft in the comedy production world, but they just know exactly what costs what. Bill’s done nine specials or something, so he knows exactly what everything should cost.

And the title. You mentioned you’d contemplated others. How did you ultimately land on Crazy Good?

Because it’s basically saying, like, crazy is good. I mean, I thought crazy bad, but crazy good. It really is the straw that stirs the drink, bad mental health. Even in some ways, what got me out of my depression was a hard reset of my brain with ayahuasca and DMT. It’s very dangerous and so I recommend it cautiously. Things got a little dicey there for a bit, and now I’ve come out of it better. What do they say? It’s always darkest before the dawn.

You reference a lot of your famous friends in this set, whether it’s Ellen or Joe Rogan or Chappelle. Do you give them a heads up before doing so?

Yeah. I didn’t want to sneak up on anybody, so I’ve sent it to Ellen, to Kevin [Hart], to Joe. The funny thing with Dave is that I was trying to figure out how to say what ended up being, “What do the clowns think?” I was trading calls with him that day, being like, “I don’t know how to say that it’s stupid that people rely on you,” and we literally kept missing each other. And then I just said it at the second taping and it worked and I was like, “Thank fucking God.” But yeah, I didn’t sneak up on anybody. These people have all been good to me, so I’m not going to be like, “Oh, by the way…” or “surprise motherfuckers.” I’m doing Joe’s podcast in a couple of weeks. Ellen, I saw three weeks ago. Dave, I see all the time. And they know where I’m coming from with all this. The weight of morality shouldn’t be on the shoulders of comedians.

Back in 2019, I profiled you, and the thrust of the piece was about how you’d been a sort of comic whisperer to the giants for so long, and increasingly you were moving into a spotlight of your own, which you were nervous about. You’re firmly in that spotlight now, and I’m curious how comfortable you are in the position?

Yeah, I’m far less impressed with other people. (Laughs.) Honestly though. I mean, it just gets to the point where it’s like, I don’t know man, I must be pretty good, and I can’t keep warming my hands off their fire, so to speak. So, I don’t know if we’re peers, but I’m certainly looking up less.

Makes sense. Before I let you go, when you look out at the comedy landscape now, at the next generation, who excites you?

I like Brian Simpson. I like Fahim Anwar. Who else do I think is funny? Think Neal, think. Lara Beitz is funny. Yeah, those are some good ones.

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