When Colbert’s jokes make obvious points, they feel weightless, but bolder ones risk feeling trivializing. Illustration by MVM

For longtime Stephen Colbert fans—and I’ve been one ever since “Strangers with Candy,” from 1999—the comedian’s move, in 2015, from Comedy Central to CBS, where he replaced David Letterman, was not a promotion. It was a gamble: he was trading a mod Vespa for something more like a pre-owned cruise ship, contractually obligated to make stops in Aruba. But nobody wants to be a hipster buzzkill, dinging a hero for selling out. “If anyone can jolt a genre that feels near-paralyzed, he’s the guy,” I wrote, the year before his début on “The Late Show.”

On “The Colbert Report,” Colbert created a persona—a Bill O’Reilly-inspired blowhard—that evolved into a surprisingly flexible instrument. By wearing a mask made of his own face, he inflected every interaction with multiple ironies, keeping his guests—including politicians and authors—off balance, and forcing them to be spontaneous. It was a friendly form of compulsory improv, which made both sides look good. Putting quotes around “Colbert” had other positive effects: it let the host express fury without becoming, as his former boss Jon Stewart occasionally was, a tiresome scourge. In 2006, Colbert’s icepick routine at the White House Correspondents’ Association dinner, in which he mocked the Bush Administration’s crimes to its members’ faces, using their words, was legendary. What would it be like for him to own his jokes and express his true opinions?

A pretty muted experience, as it turns out. As with many talk shows, the early days of “The Late Show” were wobbly, at best—and wobbly in a way that suggested the genre’s limits. With the irony drained away, Colbert was less vivid. He had a try-hard earnestness, a damp corporate pall; he was courtly with guests, as if modelling bipartisan behavior. Taking off the mask had made him less visible, not more. Then, gradually, as Donald Trump ascended, Colbert began winning praise. According to the conventional wisdom, the host had grown claws—he had found something to be angry about, at last. Jimmy Fallon’s hair-ruffling sycophancy, on NBC’s “Tonight Show,” was becoming a turnoff. Maybe this was just the news cycle, the ordinary flow of backlash and buzz. Or maybe it was Colbert’s moment. Post-November, he got the ratings to match the hype.

When I caught up recently, it was clear where the excitement was coming from. Certainly, Colbert seems electrified by the political crisis—in his opening monologue, he’s obsessed, as so many of us are, by the latest absurdities out of Washington. Because he’s always been a moralist (with a Southern, Catholic, mad-dad bent), his jokes have an ethical spark. One night, Colbert opened the show with a clip from the Conservative Political Action Conference, in which the President complained that anonymous sources called him a “horrible, horrible human being,” but never to his face. “Sir!” Colbert announced. “It would be my honor to say it to your face.” He moved downstage, toward the camera, and began to mash his face up against the lens. “You, Donald Trump, are a horrible human being.” Then he licked the glass.

Plenty of his gags are keepers. “I’m starting to doubt the effectiveness of Dr. Bannon’s Anti-Muslim Toad Oil,” he pondered, after the health-care bill crashed and burned. And yet even as I watched him throw dart after dart at the swollen targets now available—Russia, Pence, Spicer, golfing, pussy-grabbing—my mind kept drifting. In theory, the current political moment provides a brilliant opportunity for zingers. In practice, we’re living through a glut, in which no joke feels original and few feel sufficient. A repeated sketch called “Leak-Crets,” in which Colbert parodied Deep Throat, was limp. Smutty jokes, about Devin Nunes’s head up Trump’s butt, felt cheap. Attacking Trump isn’t in itself subversive—and there’s a Goldilocks dynamic to the whole endeavor. When Colbert’s jokes make obvious points (about nepotism, say), they feel weightless, but bolder ones (about Putin murdering journalists) feel trivializing. Under an absurdist regime, intensified by the digital landscape—in which few people watch more of a late-night talk show than a “bit” gone viral—all jokes become “takes,” their punch lines interchangeable with CNN headlines, Breitbart clickbait, Facebook memes, and Trump’s own drive-by tweets, which themselves crib gags from “Saturday Night Live.” (“Not!”) Under these conditions, a late-night monologue begins to feel cognitively draining, not unlike political punditry.

Meanwhile, Colbert’s interviews are pleasant but stiff; in the promotion-heavy CBS context, even cerebral decency can harden into a brand. And, though Colbert is gentlemanly rather than bro-ish, his manner with female guests (of which, to his credit, there are many) has odd pings of condescension. “I’m a huge fan of yours, too, ever since I saw you crying in a shower,” he said to Glenn Close, referring to her nude scene in “The Big Chill.” The following week, he told his bandleader, “We’re gonna have Jane Fonda and Lily Tomlin sitting over here. . . . I have made out with one of them! . . . Don’t tell my wife.”

The truth is, hosting a late-night network talk show is a bit like planning a wedding. Even if you dress in jeggings and say your vows in Klingon, your anti-wedding is still a wedding: the shape dictates the content. Colbert has grown more confident in his role, and he’s a better option than Fallon: sharper and more grownup, less of a flack and more of a thinker. But that’s a low bar for praise.

It’s not Colbert’s fault that we’re at such a funky, fraught moment for political comedy. In its first few decades, comedy creators fed off the pomposity of network news; as a result, we got delicious inventions like Ted Baxter and Bill McNeal, “SCTV” and “Weekend Update.” The two genres developed side by side, united by shared clichés. White male comedy-show hosts conventionally riffed on the conventions of white male news anchors. A late-night monologue was a warped newscast. An anchor and a host had the same daily task, seated at twin desks, asking questions in our name. Both jobs were cast as “dad to the nation”—one solid guy (always a guy) selected to tell the truth. As Walter Cronkite went, so went Johnny Carson. Making fun of the news was the comedy of small differences.

Then, in the nineties, Fox News emerged. The network branded itself as the home of punk outsiders, zinging the liberal mainstream with the studied cockiness of a finance guy who considers himself hilarious. Fox’s journalists, with their fluid approach to facts, undermined not just the notion of objectivity but the older split between stiff anchors and loose comics. A satirical arms race ensued. For liberals, Comedy Central, with its stars Stewart and Colbert, provided an antidote to Fox—but also a news source in itself. As news anchors aped comics, and comics fact-checked anchors, the categories of who was the serious one, the moral one, the self-righteous one—and who should be tweaked for self-righteousness—blurred for good. This was true even before the Internet became a factor, muddying further the question of what qualified as satire and what was “fake news.”

Maybe it’s unfair to expect more “Colbert” from Colbert. There are nights when he’s still a marksman, nailing the day’s hypocrisies. But, in 2017, it doesn’t seem outrageous to long for a talk-show host famed for his ethical clarity to deliver something tougher: comedy more like reporting and less like op-ed. Peers of Colbert’s—many of them “Daily Show” alumni—have been doing just that, on “Last Week Tonight with John Oliver” and “Full Frontal with Samantha Bee,” as well as on the surprisingly aggressive and likable “Late Night with Seth Meyers.”