Barack Obama fills whatever space you put him in.

Make him president, and he’ll seem presidential. Make him a law professor, and he’ll seem professorial. In some other universe, there’s probably some alternate version of Obama who became a novelist and is widely regarded as one of America’s foremost men of letters.

This is not to say Obama is multitalented — though he is — but rather that he boasts the chameleon-like ability to make himself seem like a natural fit for wherever he ends up. I’m sure some of that skill can be attributed to his DNA and his upbringing, a biracial child being raised by his white grandparents. (He’s made that argument himself in both of his memoirs.)

But just as much has to do with his confident, observational demeanor. Obama is great at hanging back, then delivering exactly the right quip at exactly the right moment. It’s easy to imagine him as the guy at the edge of the room, offering trenchant commentary about everybody dancing at its center. He belongs everywhere and nowhere all at once, and that can be disarming.

As Obama told the Atlantic’s Ta-Nehisi Coates of his days on the campaign trail:

If I walked into a room and it’s a bunch of white farmers, trade unionists, middle age — I’m not walking in thinking, Man, I’ve got to show them that I’m normal. I walk in there, I think, with a set of assumptions: like, these people look just like my grandparents. And I see the same Jell‑O mold that my grandmother served, and they’ve got the same, you know, little stuff on their mantelpieces. And so I am maybe disarming them by just assuming that we’re okay.

This made Obama a pop culture president unlike any other. Bill Clinton was known for turning his considerable charm on anybody he met — talk show host and voting citizen alike. Meanwhile, George W. Bush often seemed like something of an awkward uncle, laughing at people’s jokes but not getting them.

But Obama was as comfortable on Fox News as he was on The Daily Show or reading mean tweets on Kimmel. He could play games with Jimmy Fallon or talk policy with journalists, and act demonstrably different with both. It often seemed like he truly understood pop culture, particularly hip-hop and prestige TV, the two most dominant cultural forms of his era. It was like he chose a persona for each occasion — goofy but proud dad, cool guy, serious wonk — and then stepped into it.

In this way, as in so many others, the man who is replacing him is his exact opposite. Barack Obama wears many hats. But Donald Trump is always Donald Trump, for better or worse.

Obama was roundly praised for his pop culture acumen. But was that acumen as useful as it was assumed to be?

It might seem hard to believe now, but when Obama appeared on Jay Leno’s Tonight Show early in his presidency in 2009, it was the first ever appearance from a sitting president on a late-night talk show. And he followed it up with appearances on every major late-night show that aired during his administration. Throw in Michelle Obama’s appearances on a host of other programs, and the Obamas’ casual domination of pop culture seems either calculated or effortless depending on the color of the lenses you choose to wear. (It doesn’t hurt that both halves of the couple are natural-born joke tellers, a skill that few presidents or first ladies possess.)

I’m speaking as if Obama purposefully leaned into whatever TV show he was appearing on (even the news), but that’s not strictly accurate. Sure, he chose which modes and tones to use in each situation, but he always had a certain sense of gravity to him, even when he was slow-jamming the news. Obama’s strength was in finding a way to move toward the center of the pop culture solar system but also pull it toward him, so they met in the middle, instead of awkwardly waving at each other across a wide gap.

Obama also curated the pop culture he consumed in a way that made him seem populist but still pretty cool. He watched Homeland when it was new and buzzworthy, and was the only person in the world to receive Game of Thrones season six screeners from HBO before the episodes aired on television. He liked Hamilton before it was cool.

Where Ronald Reagan had regularly hosted film screenings at the White House to swells of publicity (fitting for a former film actor and Screen Actors Guild president), Obama seemed to understand that his cultural moment coincided with a cultural moment for hip-hop and prestige television — and adjusted his viewing patterns and guest lists accordingly.

I don’t mean to sound cynical. Obama has been performing this sort of softshoe his whole political life. It’s why he rarely says something truly incendiary, but also why his supporters so often wish he would. To be Obama — to be black, but also have white heritage, but also participate in power structures still primarily designed for white men — is to tread carefully to a fault. He possessed immense power but often carried himself as an outsider, which is basically a description for every mega-celebrity ever.

Hollywood responded in kind, providing him with copious public support while also giving some Americans the sense that Obama was increasingly “out of touch” or didn’t understand the plight of those who didn’t regularly pal around with Beyoncé or Lin-Manuel Miranda.

I have always bristled at the idea that Obama’s pop culture savvy is genius, or central to his appeal, or something similar. I think it might be central to his appeal to his most fervent supporters. Indeed, I’ve loved a great many of his TV appearances. But I’ve also often wondered if they worked against him, chipped away at some of what made him relatable.

Look at other presidents when they would intersect with pop culture, and you can see the flop sweat. Clinton was better at it than Bush, but only in the sense that there was something weirdly charming about Clinton when he was trying too hard. Watch his famous 1992 appearance on The Arsenio Hall Show, and you can see how much effort he’s investing to make everybody love him. (Whenever Bush crossed over into pop culture, he usually seemed like he was terrified he might forget his lines.)

Obama never lets you see any uncertainty. And when you consider that his primary outreach to the average American — especially in his second term — has come from appearances on TV shows, the picture becomes more complicated.

In 2008, Obama ran on a campaign of understanding people’s pain, if maybe not feeling it. He and his wife had just paid off their student loans a few years prior! They shopped at Target! They weren’t like you and me anymore — it would be hard for a US senator to not become part of the system — but they were close enough to those days to remember.

Trace Obama’s pop culture encounters throughout his two terms, however, and you see a guy who increasingly seems almost more at home amid the laughter and lights of the Hollywood stage. Mind you, I don’t think that’s literally true — Obama’s talent, again, is making you think he’s comfortable in pretty much any situation. But if you were a very particular sort of voter, one who thought the “coastal elite” had forgotten about the little guy, Obama’s looseness on late night played into a very old, very persistent criticism, one from the earliest days of his political career.

Donald Trump is a pop culture wrecking ball. That makes him easier to relate to.

One of the right’s most persistent slurs against Obama during the 2008 election cycle was that he was running solely for his own ego, to become famous (as if the campaign itself hadn’t already made him famous).

To many on the left, this suggestion seemed ridiculous; Obama clearly had a whole platform he wanted to enact. But his level of fame and celebrity — and celebrity support — caused many on the right to see Obama as a vacuum. He came to stand for essentially any policy or program they could think of that they disagreed with, to the point that when Obama’s plans were inevitably more moderate or even right-leaning than they expected, it almost didn’t matter. The person selling them was a symbol of a coastal elitism they feared would leave them behind. (I should note here that Obama’s race also played a role, though I will come back to that.)

The cottage industry of easily disproved rumors that sprang up around the Obamas (like one declaring Michelle Obama to be a trans woman) makes more sense in this context. Yes, the right had done something similar to the Clintons by, say, suggesting they had murdered former deputy White House counsel Vince Foster, but the Clinton family’s seeming hatred of the press and transparency provided fertile soil for rumors. Paradoxically, because the Obamas’ frequent TV appearances made them seem more open — but also like characters on a show — even the most ridiculous rumors could take root.

To be sure, much of this was because Obama is black, and thus an unusual or even threatening figure to some. But Obama was also Hollywood, and that status brought with it an additional set of cultural assumptions and signifiers. Hollywood was a place of empty vacuousness and deep debauchery. It was the last place a president should seem so cozy in.

It’s ironic that for as much as conservatives lament the left’s supposed love of celebrity, the two presidents who have actual show business backgrounds are both Republicans: Ronald Reagan and Donald Trump. This strikes many on the left, including me, as bizarre — a kind of projection onto the left of the thing many on the right apparently want (a celebrity president). But looking at Trump’s rise actually explains why this sort of candidate is so compelling to Republican voters.

Contrast any random Trump late-night appearance from throughout his decades of celebrity with any random Obama late-night appearance. Obama gently takes control of the show, while Trump just seems a little desperate to be liked, to fit in. Showbiz was never Trump’s natural home, but he wished it could be. That desire to be liked meant hosts could mock him endlessly and he would take it.

Here’s David Letterman, speaking to the New York Times:

I’ve known Donald Trump for a long time and I always thought he was exactly what New York City needed to have: the big, blowhard billionaire. “By God, I’m Donald Trump and I date models and I put up buildings, and everything is gold.” Nobody took him seriously, and people loved him when he would come on the show. I would make fun of his hair, I would call him a slumlord, I would make fun of his ties. And he could just take a punch like nothing. He was the perfect guest.

With that quote in mind, watch Obama’s 2011 White House Correspondents’ Association Dinner evisceration of Trump’s pursuit of Obama’s “long-form birth certificate.” Trump laughs along, but you can visibly see, even from very far away, how uncomfortable he is. Even Obama’s milder zingers are clearly rattling him.

Trump is happy to be humiliated, but usually only on his terms. (See also: the list of topics that were off limits for his Comedy Central roast.) Now he was being mocked when he didn’t expect to be, and savagely so. If you can put yourself in Trump’s shoes, even for a second, it’s easier to understand just how his supporters gravitated toward him as an exemplar of their many grievances, of the way the world seemed less attuned to them than ever before.

In a way, Trump and Obama’s TV personas perfectly exemplify their approaches to politics. Obama uses his wit as a tool. He can take it, and dish it out, and that makes him feel at home. But above all, he has to keep smiling. A lifetime of being a black man in America has made him understand that, if nothing else. You can only commandeer the stage if you don’t seem too threatening.

Trump, however, is a boulder. You can land punch after punch after punch on him, and nothing will happen, until he abruptly rolls forward a couple of seconds later and crushes you. Donald Trump has been the butt of the joke — from late-night comedians, from regular people, from presidents even — for decades now, and even after an election he won, he’s spent an inordinate amount of time on Twitter trying to get people to stop making fun of him. Maybe all those years of grinning and bearing snipes and snide remarks were preparation for rolling forward, just a few inches.

No matter what situation he’s in, Trump will never be talented enough to tell jokes or keep his cool during interviews or spar with the hosts, but he’s somehow more interesting for that, because he keeps trying. (See Emily Nussbaum for more on Trump’s standup-esque delivery.) He’s always been a very rich white man in a country that bends itself to the whims of very rich white men. Why appear on TV at all? Because he likes the attention.

If I were to zero in on Trump’s Achilles’ heel, it would be that he needs our love, and especially needs our love if we’re famous people. It drives him a little nuts when he can’t get it. There’s a reason he rarely passed up a media opportunity in the early days of The Apprentice, back when nobody could get enough Trump. Watch how he lights up in a room full of applause. As his approval ratings sink, it’s not hard to imagine that neediness driving him into some sort of endless circle of self-destruction.

And yet if I’m being honest, it’s far easier to identify with that need to be liked than it is to identify with Obama’s outsider cool. Barack Obama’s pop culture persona was the guy you maybe wanted to be someday when you grew up; Donald Trump’s is the guy most of us already know we are, flailing and fumbling and as likely to hold on to petty grudges as anything.

Do I want that man to be president? Not particularly — but I’d be lying if I said I didn’t see something of myself in him.