His stand wasn’t without controversy. In the same interview, Thompson also said that the show’s casting directors didn’t tap more black women because, “in auditions, they just never find ones that are ready.” But the resulting uproar ultimately led to the hiring of Jones and Sasheer Zamata in 2014, the former of whom has become his close friend and essential sketch partner, including in their popular “Black Jeopardy!” skits.

Those bits, scripted by Tucker and Michael Che, are a rehash of an old Will Ferrell franchise, Thompson points out—though Thompson owns the role of host Darnell Hayes (a.k.a. “Alex Treblack”) so completely that I had never thought of it that way. Still, he’s proud of the sketches. “It’s nice when you can make a nice living-room splash like that,” he says, “when it becomes, like, dinner talk: ‘Oh my God, they were so on point with this, or so on point with that.’ ”

The newer hires—even though Zamata has left the show, it’s now got Jones, Che, Redd, Melissa Villaseñor, and Ego Nwodim on its roster—have allowed S.N.L. to explore difficult subject matter (which, to be clear, Thompson has never avoided) with more complexity. Thompson and Jones recently did a sketch based on R. Kelly’s flabbergasting interview with Gayle King, in which the musician claimed innocence against the charges of sexual misconduct that have marred his career for decades. How do you tackle a subject like that, doing an impersonation of one of the most reviled men in R&B without belittling the seriousness of the subject?

According to Thompson, the key is not to worry too much about the impersonation. “It’s like [you] don’t even really want to get that close to being that guy,” he says. “You know what I’m saying? I’d rather point out the absurdities of that interview. But not that the situation is absurd. And then it was written very well down that road, too—him wanting to be called victim and that stuff, too. It just helped play into that ‘I’m innocent, man.’ And that could be anybody. But we all know that it’s R. Kelly because I’m dressed like him, and I’m talking to Gayle.”

Even in a situation like this, what matters most to Thompson is finding the bright spots in a dark story—for all of our sakes. “We want some relief of the pressure of the seriousness of everything,” he says. “You know what I’m saying? Like, I know it’s serious, but that interview is kind of funny. And it’d be kind of funny to laugh at him, if we can find a way that’s not disrespectful of the situation.

“And it also keeps it fun for me. Doesn’t make it such a heady type of approach. It’s stressful enough doing live TV, you know what I mean? I might as well have fun.”

It’s a reflective tone he hits more than once during our interview. Again, Thompson never says whether he’ll be leaving his post at S.N.L.; weeks after we speak, he’ll tell Ellen DeGeneres that he plans to stick around, maybe until 2020. “It’s the best job in the world,” Thompson will say. “I can’t see myself just walking away from it like that.”

When we speak, though, Thompson certainly seems to be surveying his time on S.N.L. with some wistful pre-nostalgia. “I might as well have fun,” he repeats. “I mean, it’s 16 years’ worth of stress. Looking back on it, I wanna be like, ‘But yeah, I had fun at the same time.’ ”

And where he once viewed his early S.N.L. years somewhat sheepishly, he seems now to be coming full circle.