Dave Chappelle and Dave Chappelle. Photo: Netflix

The first time I saw Dave Chappelle perform live, he was at home. Fresh off the first season of Chappelle’s Show, he was riding high, having just created a beloved, acclaimed, and still relatively cult comedy show, unaware of the craziness that would come with the second season. I had just finished high school and used a fake ID to get into the late show at the Comedy Cellar. By 2 a.m., the show was over and I was right on schedule to catch one of the late trains back to Long Island. Then, the emcee came back onstage: “Do you guys want to stick around for a special guest?” Sure, we shrugged. “Mr. Dave Chappelle!” My friends and I couldn’t believe it. This is Dave Chappelle, from the sketch show we’d been watching religiously. Dave Chappelle, from the all-time classic special, Killing Them Softly, that we’d been quoting for years. Dave Chappelle, from the Def Poetry Jam appearance that we watched and rewatched like the sensitive nerds we were. The excitement I felt then would go unmatched until I saw Steve Martin return to stand-up 13 years later. We sat down when Chappelle hit the stage, and so did he. And then he asked for a cigarette.

I would later learn this was not unusual. Chappelle likes to go onstage at comedy clubs and just hang out for a while. And that’s what he did that night. When he had nothing else to talk about, he left. There was no closer or callback. He was just done. The emcee and most of the Comedy Cellar staff had left, so he essentially walked out in front of us. Cameras didn’t have phones then, so he shook a few hands and got into an Escalade that was waiting for him. It was then we realized it was after 4 a.m. and we had missed all the late-night trains. We were stuck in the city until the morning. But we didn’t care, because in a night of ten-minute sets, Chappelle had just talked to us for two hours. He did nothing I’d consider material, save for talking about how he’d like to marry Oprah — an idea that eventually found form as a sketch on Chappelle’s Show. Some of it was funny, but mostly it was captivating to watch him think in public. Last night, again at 2 a.m., I found myself watching two hours of Chappelle doing comedy, as he released two of his three promised Netflix stand-up specials, his first since 2004’s For What It’s Worth. The material was much more polished, but there were two clear similarities: Chappelle was having a good time and it was captivating.

As you can see here, Chappelle shows again that he’s king of the punchline:

To understand what is exceptional about The Age of Spin: Live at the Hollywood Palladium and Deep in the Heart of Texas: Live at Austin City Limits, you need to start with how other comedians see Dave Chappelle. When other stand-ups praise him, it’s usually one of two things. First, it’s his comfort onstage and the audience’s comfort with his comfort. Recently, on an episode of my podcast, Good One, I spoke with Neal Brennan, the co-creator of Chappelle’s Show, about working with his old friend again when he hosted Saturday Night Live. He brought up watching the monologue with Chris Rock, and how they both remarked upon Chappelle’s stage presence. “Rock and I are watching it and Rock the whole time is going, ‘Don’t look down. Don’t look down. Stop looking down,’” Brennan told me. “Chris is worried about looking down. If Chris looks down, it’s death. If Dave looks down, it’s not.” Rock is one of the greatest stand-ups ever, but if he goes onstage and just talks instead of performing, the audience loses steam. If Chappelle’s audience is asshole-free — which can be a big if — he doesn’t really have to do much. He’s been performing since he was 14, so he is equally comfortable onstage as he is off.

The second thing I’ve heard came from a junket interview with Kevin Hart, where he explained why Dave Chappelle is the greatest living comedian: “He takes it so far left and brings it back, in ways you’d never think. None of his jokes you see coming. None of his punch lines you see coming.” Chappelle, at his best, pushes how far an audience will go with him on a flight of fancy. Chappelle’s is a comedy of enjoying himself. In the late ’90s, when Chappelle came to prominence in New York, it was the era of killers — comics who went onstage not to be liked or have fun, but to destroy the audience — but Chappelle wanted to have fun. He likes to play onstage. This is at the core of his departure from Chappelle’s Show, as fame and media attention made that show no longer enjoyable to make. So, he stopped.

If one thing is clear in his two Netflix specials, Dave Chappelle is having fun. There are frequent occurrences of Chappelle’s signature performance tic of saying a punch line, then laughing at it so hard that he lets the mic drop and hit his leg. It might seem minor, but it is at the heart of Chappelle’s comedy. Laughing at your own jokes used to be seen as hack — or at least, uncool — but after Chappelle it became much more commonplace. (Just watch Kevin Hart.) Chappelle laughs a lot through both of these specials.

Both sets start off with Chappelle talking about shows that went poorly. Deep in the Heart of Texas has a story about when an audience member threw a banana peel at him. The Age of Spin has a story about when some rappers got him high before a show in Detroit. He addresses an article about the show that said he was “booed offstage,” by saying, “I was booed; I did not leave.” It gets worse, “Because not only did I bomb — nigga, I had to go back to the very same room the next night and do it all over again.” He continues, “That would be like if you were having sex with a woman and — for some reason, this would never happen, but for some reason — she had a mousetrap in her pussy. And you get caught in the trap. And then you got to fuck her again tomorrow night. I’d still do it, but I’d be careful the next time. ‘The ol’ mousetrap in the pussy trick, eh?’ Fool me once …” And then he laughs. That is exactly the type of joke Hart described. Both stories functioned the same way, essentially telling the audience, “You might have heard I’ve had some bad shows, but this isn’t going to be that. We’re going to have some fun!”

There are also moments of brilliance in both. The Age of Spin, which is ordered first, was actually taped a year after Deep in the Heart of Texas, and you can tell. Chappelle is more confident and the show is tighter, operating around the framing device of the four times Chappelle met O.J. Simpson. The O.J Simpson stories, each funnier than the next, allow Chappelle to flex his unique skills as a storyteller. The best Chappelle stories play out like one-man performed sketches, with him setting things up and then inhabiting different characters as the story progresses. Chappelle also has an unmatched ability to play with the truth, in that you’ll believe him no matter how far he goes. And lastly, at his best, Chappelle is patient. In this excerpt from the third O.J. story, see how all of that comes together, as he talks about O.J. coming backstage after a show in Miami:

“I’m just telling you what I saw, with my own eyes, you can believe me, or not believe me, but, in my experience, O.J. Simpson … one of the nicest men I have ever met. He was nice to me. He was nice to my friends. The conversation was filled with warmth and levity and humor and wisdom. We talked for 90 minutes and then suddenly the Juice said, ‘You know what? I got to be going, but it’s good to see you again and I’m glad things went so well.’ I said, ‘Thanks, Juice.’ And my friend said, ‘Good-bye, Mr. Juice.’ They’re new to the game. He said, ‘No, thank you for your hospitality. Good night, guys.’ And we said, ‘Good night.’ And he just walked out of the room. And as soon as the door closed, we all looked at each other like, That nigga did that shit.”

Deep in the Heart of Texas is much looser. At its worst, there is a meandering quality to it: Ray Rice is brought up more than once, not as much a callback but as if Chappelle forgot something he wanted to say on the matter. But at its best, there is a thrilling chunk in which Chappelle asks the audience for a cigarette as he sits down to talk about the word pussy and a variety of pussy-related matters. It’s all deeply silly — a characteristic of Chappelle’s material that isn’t mentioned often enough — and fascinating in a “dumb thoughts from a genius” type of way. It is also the first time I’ve seen his late-night-club style caught on film.

The biggest problem with Deep in the Heart comes from a combination of topicality and the fact that it was recorded two years ago. No matter how funny, it’s hard to care about a Paula Deen joke in 2017, let alone a Donald Sterling one. The Age of Spin succeeds because Chappelle focuses less on current events and more on the culture surrounding them. In a particularly inspired section, he talks about what it was like seeing the Challenger explosion as a kid and how today, because of the internet, every day there’s a new Challenger explosion. When he discusses Bill Cosby’s sexual-assault trial, it doesn’t come off as tired, despite how much Cosby has already been talked about. Chappelle, unafraid to be on the wrong side of an argument in a joke, is candid about his personal difficulty in believing that Cosby would do such a thing. Chappelle definitely approaches a line here — and potentially crosses it as he expands upon the topic — but it mostly works. With both bits, he successfully uses his age to argue from a point of experience, instead of just being an old man shaking his fist at change.

This is not, however, always the case. In both specials, Chappelle’s comfort and irreverence lead him down a path to some truly unfortunate jokes. Most prominently, Chappelle’s absurdity can lean toward glibness and offensiveness when it comes to jokes about LGBTQ issues. Some of it comes from a position of support, but it’s hard to defend a joke like, “Turns out ‘Q’ is like the vowels, that shit is ‘sometimes Y.’ It’s for gay dudes that don’t really know they’re gay, you know, like prison fags, who are like, ‘I’m not gay, nigga, I’m just sucking these to pass the time.’” Since Chappelle derides bloggers in Deep in the Heart, let me be clear: I think comedians have the right to say what they want. I also understand that comedy is a safe space for people to indulge negative thoughts. But that doesn’t mean a joke like this one — or one that suggests that instead of doing away with the term “husband and wife,” a gay couple should just say, “Whichever one of you is gayer, that’s the wife” — are good, fresh jokes.

This is all to say neither special as a whole can touch Chappelle’s best hour, which, in my opinion, is still Killing Them Softly, but they do have moments of brilliance. The Age of Spin has multiple sections where it’s clear that he’s one of the all-time greats. A joke about Care Bears masterfully builds to a beautifully stupid punch line. His story about coming to terms with Kevin Hart’s success is both hilarious and honest, and stacks up against anything from Chappelle’s Show.

Watching these specials late at night, I kept going back to one question: Why release both together, especially when Deep in the Heart is so clearly worse? Perhaps it was the money. Now, I don’t think Chappelle signed a deal for three specials because he desperately wanted $60 million. Walking away from Comedy Central’s $50 million proved money is not what motivates him. However, being the comedian he is, maybe Chappelle saw an effective way to make a point, as he told Allen University: “The idea of being courageous is that even though you’re scared, you just do the right thing anyway. So in 2004, I walked away from $50 million. And in November, I made a deal for $60 million.” Or more likely, it’s all about optics. By releasing these specials together, with another promised down the line, this doesn’t feel like a comeback. It feels like a document of a person who has been coming back. Just like the two hours I watched 14 years ago, watching these two hours makes it feel like Chappelle is working toward something. It’s his way of telling us, “I’m around, I’m doing shows, and I’m having a great time.”