Dave Chappelle. Photo: Mathieu Bitton

Last night, Dave Chappelle kicked off a 16-show residency at Radio City Music Hall with a four-hour, guest-filled marathon, one that put Judd Apatow in the same lineup as Fat Joe. It was a little over three years since Chappelle’s last run of performances at the historic theater, but this show was different. Chappelle was different. And more than anything, the audience’s relationship to Dave was different.

At the time of his 2014 residency, we were long removed from Chappelle’s Show, and the comedian playing Radio City felt like a comeback. It represented the culmination of the Dave Chappelle legend, a myth defined both by his time in the limelight and the way he stepped out of it. Overblown stories of bad shows and his history of walking away made the first run feel like you were catching something fleeting. This was seemingly your last and only chance to see one of the all-time greats, a reclusive comedy legend who, in the previous year, had been written about in Jason Zinoman’s terrific Kindle single Searching for Dave Chappelle and Rachel Kaadzi Ghansah’s classic piece “If He Hollers Let Him Go,” subtitled “Searching for Dave Chappelle ten years after he left his own show.”

Well, the search is over; Chappelle is everywhere. He hosted SNL and released two specials on Netflix. He’s no longer a concept, but a stand-up like any other, trying to make you laugh with his observations about the state of things. You could feel the shift, as the initial fawning reviews for his Netflix specials were slowly followed by condemnations for some of the content. And both takes were correct: Those specials included some of the absolute best and worst stand-up of the year. Much of Chappelle’s material was thoughtful and masterfully paced, easily clearing the super-high expectations set for him. But those sets also contained jokes that were surprisingly glib and callous. It’s not just that he tried to make jokes about trans issues; it’s that those jokes were sloppy and shallow. In the wake of that, we had to reevaluate how we were assessing Chapelle; he no longer can nor should be judged on a comeback curve.

All of this is to say, Chappelle was off his game last night. Much of the material felt unfinished and unfocused — he even said at one point, “You know, it doesn’t sound that funny, but one day I’ll do that somewhere and that will be a fucking classic” — with Chappelle bringing up topics only to quickly move on from them. But his exactly hour-long set wasn’t a classic Chappelle sit down, smoke a cigarette, and riff on whatever comes to mind kind of performance. He was clearly doing material. It’s just his material felt like a work in progress, which may not be what people paying upward of $200 for tickets had in mind.

He opened with a story about getting booed in Cleveland because he made jokes about the Facebook killer, which mostly functioned as a warning that he was going to go “hard in the paint,” in his words, by touching on some sensitive areas. This was immediately confirmed: For about the first 20 minutes of his set, Chappelle almost exclusively talked about trans issues. I’m sorry to report, he does not seem to have read everyone’s think pieces about how the trans material from his specials was problematic, and if he did, he only saw it as a challenge. He started by talking about how he was “shocked!” by Trump’s ban on transgender officers in the military, because he didn’t realize there were any trans people in the military. “Sounds like a secret weapon to me,” he continued. “If I was in ISIS in the trenches fighting against the United States and all of the sudden I see a man with a beard and big D-cups titties just rushing my foxhole and shit, I’d be horrified.” That joke and others in this section suffer from the same problems as those from his specials — they are rooted in disgust and generalization. They’re just not good.

Later, he told a story about receiving a fan letter that derided his trans jokes, to which he replied, “A weird thing happened to me in this moment — it honestly made me feel bad that I made somebody else feel bad.” That was, however, just misdirection for another series of trans jokes. He went on to say he didn’t know what joke they were referring to, because he has so many jokes about trans people, but he thinks it was probably “this joke I’m about to tell you right now.” Which went like this: “I read in the paper that Caitlyn Jenner was contemplating posing nude in an upcoming issue of Sports Illustrated. And I knew it was politically incorrect to say, so I figured I’d just say it for everybody — yuck. Fuck, man, I just want to read some stats, like why are you cramming man-pussy in the middle of the sports page like that?” After that, Chappelle went back to investigating his feelings toward transgender people, saying he doesn’t understand them, but he doesn’t believe that “disqualifies them from being a human being that deserves a life with dignity and happiness and respect,” which got a lot of applause (it was a real clap-ready audience). He then tried to make a fairly complicated point about his own frustration with “all this talk about how they feel inside,” because “since when has America given a fuck about how anyone feels inside?” He ended by arguing that sometimes he thinks “the only reason all of us are talking about transgenders is because white men want to do it. If it was just blacks and Mexican like, ‘Hey, y’all, we feel like girls inside.’ They’d be like, ‘Shut up, nigger, no one asked how you felt.’”

Here’s the thing: Successful “edgy comedy” is akin to watching a tightrope walker. The tension of the risk (saying the wrong thing, falling off the rope), ramps up the potential release of the success (laughter, ooohs, aaahs). But if the tightrope walker keeps on falling off and getting back on along the way, it loses its effect and can get legitimately boring. Which is okay if you’re practicing in the Comedy Cellar at 1 a.m., but not at Radio City Music Hall. Chappelle didn’t come off as a free-speech fire starter or an inflammatory punk trying to get a rise out of people. He just sounded old and out of touch, a fact that he touched on very briefly throughout the set, but not enough.

The other half of the show focused on Donald Trump. Chappelle started by talking about his election week, from seeing “the poor whites” lining up to vote for Trump to his SNL monologue, where he said everyone should give the incoming president a chance. To which he added, “as the weeks went on, I started thinking to myself, Maybe I shouldn’t have said that shit. Because this motherfucker is clearly, clearly doing a terrible job.” The section continued with Chappelle discussing the Women’s March and pussy grabbing, among other things. The main issue here is the same one that has plagued most attempts at finding comedy in Trump: He is bad at such an incredible rate, and his badness is digested at such an incredible rate, that jokes about months-old atrocities feel dusty. There’s also the fact that both these sections aren’t part of Chappelle’s wheelhouse. As Dave Schilling wrote on Vulture around the release of the specials, “what Chappelle is not, and has never really been, is a Chris Rock–level social satirist, or a comic like Richard Pryor who put his darkest secrets on the stage for all to see. What fueled his initial popularity was his ability to speak across cultural divides by just being funny.”

I should say the show isn’t completely unfunny. There is a silly section I loved where he teases the Amish, with him joking at one point, “You don’t even know what the weather’s going to be like tomorrow.” Another joke, the one Chappelle said was unfinished, legitimately found a new take on Michael Jackson. The best parts unsurprisingly came when Chappelle focused on himself. He told a story directly to 50 Cent, who was in the audience, about how growing up in the suburbs was worse than the hood because at least in the hood everyone around you is struggling, too. “You don’t know the pain,” Chappelle said half-jokingly, of going over to a white friend’s place and seeing they had all the utilities working. Best of all was a joke about getting older, where Chappelle did an impression of Morgan Freeman, if Freeman were Chappelle’s penis being jerked off. It was truly fantastic. Not sure if it was enough to justify the standing ovation he received at the end of the show, but I get it. In high school, when I saw Michael Jordan play in his final season, I gave him a standing ovation for the eight points he scored. Sometimes you just want to tell a legend you love them forever and always, regardless of the night.

The good news is, if Chappelle’s last run is any indication, the material will get better as he goes. The 2014 show I saw happened later in his run, and was half an hour tighter than the one on opening night. The other good news: After Chappelle finished his closer — a brilliant work in progress comparing Donald Trump to Emmett Till’s false accuser — the show wasn’t actually over.

As I’d learn, it was just getting started. Chappelle is joined by the Roots for the first four nights, who invited other artists to play along with them. (Chappelle called the Roots nights “Rootsapalooza,” according to Questlove.) They built an easy but energetic vibe, setting the table for Lil Wayne to come out and rip the place apart. Dude put on a show that included maybe the three funniest moments of the evening: (1.) When he struggled to take his T-shirt off over his dreads. (2.) His DJ/hype man calling him the greatest rapper alive, to which Wayne replied earnestly, “Thank you very much,” as if he wasn’t paid to say that. (3.) Wayne very sweetly brought Black Thought back onstage for them to perform together. Afterward, they stood in front of Questlove’s drum kit, Thought’s arm around Wayne. Wayne asked if someone would take their picture. Wayne then called Black Thought a “legend,” to which Thought replied, “My fellow Libra.”

After Wayne wrapped up his set, Chappelle, in full block-party mode, came back onstage to say it was the venue’s curfew and they will get taxed for every minute they go over. (This is very true. We’re talking thousands.) Chappelle said he was going to do “what no one in show business would do … niggas, we going late!” I assumed he meant one more song. He didn’t. He introduced Fat Joe and French Montana, who each played one of their songs. Then the Roots played “Seed” and a cover of Curtis Mayfield’s “Move on Up.” A nice way to end a great show. But wait — Anderson .Paak came out to perform two songs, and have a sort of double drum solo (a drum duo?) with Questlove. (There are more high-profile special guests scheduled for the rest of his run, including Chance the Rapper, Solange, Chris Rock, and Lauryn Hill.)

Chappelle came back onstage to literally shake everyone’s hand and announce, “If they fine us, it’s coming out of my check because it was well worth it.” He left, then came back again because he forgot something: “An after-show tradition.” Out walked Donnell Rawlings (who opened the show along with Apatow and Wil Sylvince), who screamed “I’m rich biatch” into his mic.

The lights came up. Eighty percent of the crowd had left or was leaving, and again Chappelle came back onstage, talking into the mic until the sound people turned it back on. He wanted to say rest in peace to Charlie Murphy. Also, he just didn’t want to leave the stage. Luckily, he has it reserved for the rest of the month.