If there's a downside to being a wildly popular talk show host who owes at least some of that popularity to the ways his clips can be easily sliced up and passed around the internet, it's that the internet is eventually going to get mad at you for something not being delightful enough, informed enough, or woke enough. And there's not a lot that's less delightful right now than watching anyone treat ridiculous possible president Donald Trump with kid gloves. So while there have been plenty of critiques of Fallon's entire Tonight Show interview with Trump (not his first, naturally), it's that brief clip of him playfully mussing up Trump's hair, summoning all the satirical mischief of a second-grader, that seems to be living in infamy (at least, you know, for the next few hours).
No one should have expected a fearsome fastball from Jimmy Fallon, who has improved somewhat as an interviewer since his Late Night days but still cannot claim that particular skill as one of his strongest. Perhaps sensing that his combination of giggling and fawning might not satisfy much in greater volume, his Tonight Show tends to get more attention for involving its guests in silly games or stunts — and you know, that's fine. It makes him a hell of a lot easier to take than Leno. Fallon is front and center for what has become, essentially, the Saturday Night Live-ization of late night. SNL producer Lorne Michaels got his foot in the door when he executive-produced Conan O'Brien's takeover of Late Night, and he stayed in place when Fallon ascended to O'Brien's chair. Fallon brought Michaels over to exec-produce his incarnation of The Tonight Show, and Michaels has remained exec-producer over at Late Night as Seth Meyers took that gig. Presumably this will still be the case when Colin Jost takes over one or both of these shows in 2025. This was allowed to happen in part because during some years of great turmoil in NBC's primetime schedule and in their late night staffing, Saturday Night Live was a relative constant; for a time, it was regularly NBC's highest-rated show of any given week.
I have no idea what Michaels' actual role is on these other late night shows. My guess is that it probably doesn't amount to much, as he still seems involved in the day-to-day of running Saturday Night Live, which returns for Season 42 in just a few weeks amidst some cast and writer's-room shakeups. But his brand is certainly all over these shows, not just in the SNL alumni who host (and in the case of Late Night, often guest). Political humor, often of the softball variety, has been a staple of late night chat shows for decades, and even the appearance of actual politicians/presidents/candidates is not especially rare, though it does seem to have accelerated since President Obama made the first Tonight Show appearance by a sitting president, back in the Jay Leno days. But a lot of these shows seem to aspire to what SNL affects: a kind of irreverent, omnidirectional satire. Michaels often makes a lot of noise about not doing ideologically based comedy, and instead making fun of whoever's in power, in the news, et cetera. It's not a bad idea in theory, though in practice it can be the comedy equivalent of the old saw about telling "both sides" in the news media, even when one side is patently insane, lying, or otherwise dangerous.
Naturally, politicians want to get in on the act; appearing on SNL during election season has become a vaunted tradition. Hillary turned up for a cutely chummy sketch last fall, where she played a bartender opposite Kate McKinnon's Clinton impression. Donald Trump, meanwhile, hosted a whole episode, leaving even hardcore fans of the show feeling a bit deflated, so unchallenged went most of his most reprehensible proposals, quasi-policies, and appalling stupidities.
Since then, Trump has only gotten more ridiculous and terrifying as he's emerged not just as a novelty frontrunner but the actual Republican nominee — a turn of events that has a nightmarish quality that cheerfully quasi-nonpartisan late night TV is not equipped to handle. Having both presidential candidates on The Tonight Show, as Fallon is doing (Hillary Clinton appears on Monday), is a perfectly normal-seeming SNL-style ritual. Everyone gets to come on and show their lighter side. But as with the news media, even treating Donald Trump as just another candidate for your vote rankles — it legitimizes his hateful rhetoric in an uncomfortable way. It's not cute to see Fallon, surely the "cutest" late night talk show host in history (though James Corden seems dead set on making a play for the title), make nice with him. It's not even that cathartic to see comedians take him on in a late night context, although props to Seth Meyers, a Lorne-approved heir who has actually leaned into political material during the presidential race, realizing his strengths as a Weekend Update anchor make him well-suited to offer jokes that go beyond monologuing about Trump's hair or "funny" way of talking or whatever (maybe it's the ongoing contrast with Fallon, himself a former Update anchor, that spurned Meyers into action, though it's unlikely he would ever admit it and risk disparaging Lorne's favorite son).
I'm always reluctant to blanket-dismiss practices in comedy. It's not necessarily productive to call it innately wrong for Jimmy Fallon to goof around with Donald Trump. Even that awful SNL episode had two sketches (both pretaped and both using Trump minimally that worked). But here's the thing about Donald Trump: He's not that funny. He's not at all funny personally — if Mitt Romney seemed vaguely baffled by the concept of humor, Trump shows a bully's disdain for it anytime it's used for purposes other than belittling his enemies. Worse, he's been continually overrated as a funny concept. Maybe he was once, circa The Apprentice, when SNL's Darrell Hammond built some amusing impression sketches around him, the best of which saw Trump presiding stupidly over a commercial for Domino's (which he insisted was actually pronounced "Do-min-io's"). But despite the retention of Hammond, now the SNL announcer, to play Trump for much of last season, SNL aired very few, if any, funny Trump-centric sketches. They'd concentrate on the ego and the speaking patterns and miss the pure hatefulness, or else not know how to deal with it but to laugh at the easy stuff. To point out that Trump carries himself as a hateful human being would apparently qualify as "partisan."
Trump's unfunniness as a person and even as a target makes a particularly poor match with Fallon's comedy-lite approach. When he does comedy bits at all, they're like poorly timed, baggier versions of SNL sketches that make you appreciate the craft that goes into a slapdash SNL bit. Most of the time what he's doing is more amusement than comedy, and it's often a smart strategy; look where trying to be funny got Leno. (Well, extremely successful and rich and beloved by a lot of people who don't really care for comedy, but still: hipster jerks like me don't like him one bit, and that's gotta eat away at a people-pleaser like Leno.) But with Trump, comedy-lite curdles even faster than actual comedy. It turns out a pompous, ridiculous, unfit-for-office pretend-billionaire isn't actually comic gold. He's more like poison. You know who's actually comic gold? Ted Cruz. Aren't a lot of us feeling nostalgic for that unelectable jackass about now?