One might imagine that jokes about slavery would be off the table in 2026. “Not at all,” Mr. Cross said. The bit, in which he imagines that he would have been a generous, benign slave owner, grew out of an exchange he had during preparation for an earlier tour. At the time he needed a setup for it, he said. “It felt like it was like, ‘Oh my, I’m trying to be shocking.’” Then he thought of tying it to a hike on the Inca Trail, built by enslaved workers. With that context, he said, it worked.

“I’ve done plenty of stuff that is, for lack of a better word, button-pushing,” he said.

Is that fun for him?

“Oh, yeah,” he said. “I wouldn’t do it if it wasn’t. It makes the set that night memorable and interesting and potentially dangerous. I mean, it’s live. That’s part of the fun of doing a live show.”