Live from New York… it’s Dave Chappelle. The controversial comedian opened his Saturday Night Live hosting gig with an expanded monologue that immediately overshadowed the rest of the evening’s sketches. Chappelle’s nearly fifteen-minute routine functioned as an extension of his divisive Netflix specials, as he offered his typically unfiltered and uncompromising commentary on such hot-button topics as the recent midterm elections, the war in Ukraine and, of course, Donald Trump.

But it was his material about the wave of antisemitism generated by celebrities like Kanye West and Kyrie Irving that took center stage. Chappelle waded into waters that he clearly knew would be tricky to navigate in front of a live audience, in addition to the millions watching at home. “Before I start tonight, I just wanted to read a brief statement that I prepared,” he began. “I denounce antisemitism in all its forms, and I stand with my friends in the Jewish community.”

With that preamble on the record, he launched into his opening salvo. “And that Kanye is how you buy yourself some time,” Chappelle joked, as he dived head-on into the controversy. “Early in my career, I learned that there are two words in the English language that you should never say together in sequence,” Chappelle noted. “And those words are ‘The’ and ‘Jews.’ I’ve never heard someone do good after they’ve said that.”

The comedian went on to recall his reaction to West’s since-removed comments on Twitter, where he threatened to go “Death Con 3” on Jewish people and immediately lost lucrative business deals with companies like Adidas and Foot Locker. “Adidas dropped [him] immediately,” Chappelle said. “Ironically, Adidas was founded by Nazis and they were offended! I guess the students have passed the teacher.”

So far, the crowd was with Chappelle as he roasted West’s actions. But things grew noticeably tense as his commentary took a turn. “He had broken the show business rules,” Chappelle said of West. “You know, the rules of perception. If they’re Black, then it’s a gang. If they’re Italian, it’s a mob. If they’re Jewish, it’s a coincidence and you should never speak about it.”

The “coincidence” that Chappelle appeared to be referring to is the misguided notion that Jews supposedly control the Hollywood media ecosystem. “I’ve been to Hollywood — it’s a lot of Jews,” he said. “But that doesn’t mean anything. There’s lot of black people in Ferguson, Missouri. That doesn’t mean we run the place! I would say if you had some kind of issues you might go out to Hollywood… you could maybe adopt the delusion that Jews run show business. It’s not a crazy thing to think — but it’s a crazy thing to say out loud at a time like this.”

As for Irving — who was suspended by the Brooklyn Nets after posting a link to an antisemitic film on Twitter and — Chappelle suggested that the NBA erred by demanding too many concessions before he could resume playing. “This is where I draw the line,” he said as the studio audience went temporarily silent. “I know the Jewish people have been through terrible things all over the world, but you can’t blame that on Black Americans. You just can’t. A fair punishment would be that he just post a link to Schindler’s List and you all write your own captions! Kylie Irving was nowhere near the Holocaust. In fact, he’s not even certain it existed.”

Not surprisingly, Chappelle’s comments generated some strong responses on Twitter, with many viewers accusing him of playing into the antisemitism that he was supposedly ridiculing. Those critics also noted the transphobic humor that was prominently featured in his last Netflix special, The Closer, and led to a wave of walkouts at the streaming service.

For his part, Chappelle seemed well-aware that he’d once again be in the hot seat after his monologue wrapped up. And that’s why he reminded audiences that he’s never sought out the kinds of lucrative endorsement deals that West’s own words cost him. “My first Netflix special… [I said] ‘I don’t want a sneaker deal, because the minute I say something that makes those people mad, they’re going to take my sneakers away,'” Chappelle said. “Now you see Kanye walking around L.A. barefoot! This guy lost a billion-and-a-half dollars in a day.”

“It shouldn’t be this scary to talk about anything,” he continued. “It’s making my job incredibly difficult. And to be honest with you, I’m getting sick of talking to a crowd like this. I love you to death and I thank you for your support. And I hope they don’t take anything away from me — whoever they are.”

Saturday Night Live airs Saturdays at 11:30pm on NBC