Bolling, who has been a Pulitzer Prize finalist twice in the past five years, makes these characters “as cute as possible while they’re doing horrible things,” he said. He’s parodied Scarry before, and the results are reliably sweet and chilling—even as we catalogue the horrors of our times, via cartoon pig and rhino and cat, it’s hard not to feel buoyed by the pleasures of Scarry’s gentle world view. “It’s very typical of a lot of what I do, which is taking older, nostalgic, innocent pieces of art and defiling them by bringing them into the darkest parts of our world,” Bolling said. “I find it’s very effective. And it can be very upsetting to me.”

“Tom the Dancing Bug,” which Bolling began publishing widely in 1990, has always been free-form and vaudevillian from week to week—original characters, recurring parodies and satires, one-offs, a terrific long-running meta-funny-pages gag. His illustration style tends toward a tidy clean-line aesthetic, à la “Tintin,” but it morphs to suit whatever he’s up to: hatched and shaded portrait-style depictions of celebrities and politicians; imitations of other artists; fake ads, posters, and informational broadsides. Early on, Bolling had “Saturday Night Live,” Mad magazine, and “Mr. Show” in mind as inspirations. The strip has become more political over time, especially in recent years, though the past few weeks of U.S. election news—an assassination attempt in one party, the passing of the candidacy torch in the other—has been atypical in its intensity. Like all satirists of our era, Bolling has learned to adapt.

For a long time, he did “the old satirist’s trick of exaggerating what happens and what politicians say and what their policies are,” Bolling told me. “But that didn’t work with Trump, because he was better at it than I was. I couldn’t compete with him in creating his own satire.” Instead, Bolling tends to recontextualize Trump, putting his language into the mouths of comic-strip characters, on propaganda posters, and so on, providing the reader with a fresh jolt of amusement and alarm. In strips from 2020, Bolling, via black-and-white newsreel-style images, juxtaposes the Trumpian response to the pandemic with the bombing of Pearl Harbor, in 1941. “Why should I join up just because a few thousand Americans died in Hawaii?” a potential G.I. asks. “How many Americans die every day in ironing board accidents?” F.D.R., downplaying the crisis, responds to enemy invasions of New York and California with “This is only in two states! I like those numbers! In a couple of days it will be zero!”

Bolling has published several collections of his work; his latest, “ ‘It’s the Great Storm, Tom the Dancing Bug!,’ ” which includes strips published from 2020 to 2023, came out this month. The cover—the U.S. Capitol, a pumpkin patch, silhouettes of rioters under a night sky—references his series “Q-Nuts,” which plays on “Peanuts” and “It’s the Great Pumpkin, Charlie Brown.” Bolling tries to resist being cruel to beloved childhood characters, “but my favorite, Linus, I turned into a QAnon nut,” he said. “And that hurt.” In “Peanuts,” Linus faithfully waits each Halloween for the Great Pumpkin, a mythical, unseen figure who delivers candy to believers. “It never happens,” Bolling said. “And he always makes excuses. I realized that’s QAnon.” It was one of his most popular cartoons ever. So was the series “Donald and John: A Boy President and His Imaginary Publicist,” with boy Trump as Calvin and John Barron, the imaginary publicist, as Hobbes. Bill Watterson’s original characters—Calvin, enthusiastic young fantasist and joyful megalomaniac, and Hobbes, slightly more reasonable sidekick—fit beautifully into Bolling’s satirical framework. (In a recent entry, a giant Calvin, outfitted with toy crown, stomps around a ravaged D.C., exclaiming, “It’s good to have immunity!”) Coming up with ideas can be gruelling work, Bolling said, but when he did a daily “Donald and John” online, in 2016, it “was like walking down the path picking blueberries. Every day I was, like, ‘Oh, that’s like when he pretends he’s a dinosaur.’ Everything fell into place.”