Donald Trump and Jimmy Fallon on The Tonight ShowNBC

Jimmy Fallon made his career as a talk-show host (first at Late Night, then The Tonight Show) by avoiding contention. The celebrities sitting on his couch can expect jovial questions about their lives and whatever new project they’re working on. At the absolute worst, they’ll be roped into performing a visual stunt or goofy sketch, but the name of the game is always having fun. That’s the gentle situation Donald Trump walked into on September 15, 2016, in the middle of his presidential campaign; what followed was the infamous interview where Fallon asked him things like, “How would your coworkers and peers describe you?” before playfully mussing Trump’s hair.

Fallon, who did not ask one substantive question of his guest, was pilloried for the interview at the time. Over the following year, The Tonight Show’s ratings slipped as late-night hosts more critical of Trump, like Stephen Colbert and Jimmy Kimmel, saw gains. By 2018, Colbert’s lead had only grown wider; Fallon’s more apolitical brand had become less of a must-see in an era dominated by news from Washington. Still, he thinks of The Tonight Show as a variety program first and foremost, aimed at the broadest audience possible, which fits the tone of the show he makes. So why is he now the latest celebrity to get tangled up in a public fight with the president?

In an interview on The Hollywood Reporter’s Awards Chatter podcast last week, Fallon expressed regret over tousling Trump’s hair, saying the blowback was “a down time” for him and his coworkers. “I don’t want to make anyone angry—I never do and I never will,” he said, choking up. “It’s all in the fun of the show. I made a mistake. I’m sorry if I made anyone mad. And, looking back, I would do it differently.” Trump replied as he often does, in a tweet, telling Fallon to “be a man.”

The most interesting thing about Fallon’s tearful remarks is not his admitting that he “made a mistake” with the Trump interview. After all, he had already done that in a soul-searching 2017 New York Times profile, saying his viewers had “a right to be mad.” What stands out is that he practically admits that it’s hard to imagine how he could’ve done things differently, outside of not inviting Trump on the show at all. The interview was Fallon at his usual level of friendliness; I don’t want to make anyone angry might as well be the host’s motto.

In a recent conversation on Jesse David Fox’s podcast, Good One, Fallon gets deeper into his philosophy of entertainment. “I just want to keep making your brain better, making you feel better, making you go, ‘Ugh, dude, I’ve had the longest day, just make me laugh. Jimmy, just give me something I’ve never seen before,’” he said. “I think it’s important just for America to have something you can watch.” That’s indeed what he’s delivering: If nothing else, The Tonight Show is a show you can watch.

Fallon’s mistake is that he seems to think he’s still broadcasting in the era of his hero Johnny Carson (who hosted The Tonight Show from 1962 to 1992). But Carson began hosting in an era of three TV channels; now, the American media landscape is splintered to the extreme. Fallon’s vision of a relaxing program that just helps viewers unwind is perfectly inoffensive, but it’s one that’s ill-suited for guest appearances by political candidates (whom he’d never want to ask uncomfortable questions of). The challenge Fallon faces in making a pointedly friendly talk show in 2018 is that every aspect of American life that he might seek to satirize—family, health, pop culture, sports, jobs—feels filtered through the political moment.

In the intervening years, Fallon has made some effort to give his topical humor a little more bite. But his heart’s never felt in it, and given the plethora of comedy programs aimed right at the president (most pointedly, there’s Comedy Central’s The President Show), it doesn’t really need to be. What’s crucial for The Tonight Show’s success is Fallon seeming genuine—something he never pulls off when attempting political comedy. In fact, Fallon recalling his mood after the hair-mussing to The Hollywood Reporter is maybe the first time I’d ever heard him express real emotion outside of talk-show-host joy. “You go, ‘Alright, we get it. I heard you. You made me feel bad. So now what? Are you happy? I’m depressed. Do you want to push me more? What do you want me to do? You want me to kill myself?’” he asked his critics.

Wanting Fallon to feel bad is something he can’t understand, he says, since it’s something he himself would never seek out for others. “Of all the people in the world, I’m one of the good people—I mean, really. You don’t even know what you’re talking about if you say that I’m evil or whatever,” he told The Hollywood Reporter. Trump’s approach to criticism is quite the opposite—if you attack him or upset him, he’ll push back. It’s no surprise, then, that Fallon’s emotional confession earned Trump’s reproach to “be a man.”

Fallon replied with some mild zingers on his own show, saying, “Melania, if you’re watching, I don’t think your anti-bullying campaign is working.” But his more impressive counter to Trump suggests that he has learned a little about how to operate in the political sphere and still maintain his sincere, good-natured image. “In honor of the President’s tweet I’ll be making a donation to RAICES in his name,” Fallon tweeted on Sunday, referring to the organization that pays for legal representation for immigrant children. The Tonight Show may never break from its mild-mannered routine, but since mussing Trump’s hair, Fallon may have at least grown a little savvier.

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