In signature fashion, the 30-year-old faced his fears head on. He came home and put Compton, the Coast, and everyone else on his back to make DAMN., a dazzling and utterly singular album that he says he recorded—and is presently touring—to bring comfort and strength to the rest of us. “LeBron James or the little boy around the corner,” Lamar tells Dave Chappelle, a comedian and cultural critic who knows a thing or two about greatness. “We come from the same struggles, and it comes out of my mouth for them to relate to.”

And if what does come out is, despite all of Lamar’s successes, still fraught with self-conscious anxiety, it seems to support the old truism popularly attributed to Bertrand Russell: “The whole problem with the world is that fools and fanatics are always so certain of themselves, and wiser people”—or, we might say, the truly righteous and brave—”so full of doubts.”

DAVE CHAPPELLE: Kendrick.

KENDRICK LAMAR: Dave. What’s going on, brother?

CHAPPELLE: The last time I saw you was in Australia with J. Cole—you had just performed with Eminem. A lot’s happened since then.

LAMAR: Definitely. How you been?

CHAPPELLE: I’ve been great. I want to start by asking you about a recent scandal in the comedy world: Kathy Griffin and the picture of her holding Donald Trump’s decapitated head. My question for you is not about politics, but about the content in your work. In comedy right now, the issue is, “When does a comedian go too far?” And I imagine in hip-hop that’s been a long-standing debate—even when I was coming up, when Bill Clinton went after Sister Souljah. When you write, how much do you think about the repercussions of anything you might say?

LAMAR: When I look at comedy—at Richard Pryor, at you—it’s all self-expression. I apply that same method to my music. I came up listening to N.W.A and Snoop. Like them, it’s in me to express how I feel. You might like it or you might not, but I take that stand.

CHAPPELLE: I have this thing when I write jokes; I call it my unseen audience. I’ll think of certain people when I’m writing certain types of jokes. For instance: “What would my mother say?” Who do you think about when you write? Are you thinking about the streets? A lot of your work is openly spiritual and contemplative.

LAMAR: I really focus on what my fans will take from it, people living their day-to-day lives. At the end of the day, the music isn’t for me; it’s for people who are going through their struggles and want to relate to someone who feels the same way they do. I’ve got to take Mom out of the equation. I’ve got to go all-in, expressing myself, right there in the moment.