Larry Wilmore and the History of the Insurgent Host

Depending on who you ask, Larry Wilmore either bombed horribly at the White House Correspondents’ Dinner, or he was the best host in nearly a decade. The crowd of journalists, celebrities, politicians, and general insiders wasn’t exactly thrilled by Wilmore’s biting remarks. He spared no one, mocking CNN’s decline to the point that Don Lemon gave the finger, while also critiquing Hillary Clinton’s disingenuousness and the Obama’s Administration’s failure to close Guantanamo Bay. While the crowd wasn’t laughing that much, one got the feeling that the folks at home – who weren’t the targets of Wilmore’s ire – were having a much better time.

While Wilmore’s mercilessness may have been unexpected to the WHCD crowd, it was really the latest example of a long-running tradition: the insurgent host. It goes like this: an elite organization throws a big fancy self-congratulatory party, only to screw it up by bringing in a host (almost always a comedian) who has no respect whatsoever for the opulence of the affair, and decides to rip the entire thing to shreds in front of an increasingly hostile audience, to the point where they become the villain of the room. The people at these parties just want to have fun without thinking about the inherent flaws within their institution. When the person brought in to bring the funny decides to hold their feet to the fire, the crowd gets increasingly uncomfortable.

Wilmore is not the first person to use the WHCD as a chance to say what really feels. A decade earlier, his timeslot-predecessor Stephen Colbert gave us one of the most memorable monologues in the history of the event, as he pointedly took President Bush to task for pretty much every poor decision his administration had made up to that point. We watch Colbert mock Bush for his 32% approval rating at the time, while giving us the now-immortal line that “reality has a well-known liberal bias,” and you can imagine that half the country (perhaps even more) was immensely satisfied by this, and watching Bush wiggle in his chair begging for it just be over already made it even better. Colbert had no interest in the decorum of the event; he was going in on Bush. The result was one of the most important pieces of political satire of the 21st century.

Now, this phenomenon does not have to be political, and one of the best examples of it came in 2010, when Ricky Gervais hosted the Golden Globes for the first time, and lit into an elite crowd of one percenters who had only wanted to get drunk and pat themselves on the back. While Gervais has hosted the show two other times since, there was something electric about his first gig, because it was so unexpected. When he jokes about the poorly-received Johnny Depp-Angelina Jolie vehicle The Tourist only getting nominated because of bribery, the sense of discomfort was palpable. Later, when introducing the main stars of Toy Story, he lists a seemingly endless number of Tom Hanks’ accomplishments, then simply says “….and the other is Tim Allen.” Allen seemed to take the joke in stride, but by the end of the night, pretty much the entirety of Hollywood was looking at Gervais cockeyed. His punishment? Being asked back to host the show the following year.

Of course, having contempt for the elite group of people you’re hosting does not guarantee that you will be a success. Consider Seth MacFarlane’s disastrous Oscar-hosting gig from 2013, which is often ranked among the worst of all-time. MacFarlane began the show with an infamous musical number called “We Saw Your Boobs,” in which he lists seemingly every movie that the women attending the Oscars bore their breasts in. Now, in all fairness, the idea behind this bit was to mock MacFarlane’s controversial nature; it was set up by William Shatner as an example of the type of unfortunate thing MacFarlane might pull. Unfortunately, that context was lost in translation, and the bit just came off as immature and sexist, embodying MacFarlane’s worst qualities. Perhaps Seth was attempting to mock Hollywood’s reliance on nudity to get people in the theater, but he ultimately felt like the butt of his own joke.

One of the few Oscar hosts remembered even less fondly than MacFarlane is David Letterman, who hosted the show in 1995. In theory, he was the perfect insurgent host. Notoriously cranky and known for some absolutely devastating interviews, he seemed like the perfect person to put Hollywood’s obnoxious extravagance in its place. Instead, he kept making that same “Uma-Oprah” joke over and over again, coming off like a stoner who is the only one in the room high enough to laugh at his own dumb joke. Letterman could have been an all-time great Oscar host if he had brought his often cruel wit to the stage. Instead, he came across more bemused than anything else, and the audience couldn’t help but feel the same way.

So, what separates a good insurgent host from a bad one? A lot of it has to do with focus. Just bringing in someone in to host the Oscars or the WHCD who might not particularly care for such gluttonous events isn’t going to guarantee a memorable night. Not if the host doesn’t have a clear target. In the case of MacFarlane, he got a few good jokes in (the line about how the actor who “did the best job of getting in Abe Lincoln’s head” was John Wilkes Booth was a bit of dark humor worthy of Anthony Jeselnik at his best), but on the whole, he seemed unfocused, and like so many of the worst Family Guy episodes, overly reliant on humor that could best be described “edgy for the sake of edgy.” Letterman, on the other hand, seemed to treat the whole thing as one big joke, and as a result, didn’t actually tell that many jokes. Colbert, Gervais, and Wilmore succeeded because they had clear targets from the beginning, and promptly destroyed them one by one.

Of course, one might ask that if these controversial hosts cause so much discomfort, why are they brought in to begin with? For one simple reason: nobody wants to appear safe. If you look at who hosts these award shows, you’ll notice there’s an endless cycle of safe hosts and insurgent hosts. People think the show has gotten too milquetoast, so they bring in a bold presence to liven things up. That person inevitably makes the crowd nervous, so they retreat back to their established comfort zone. When Colbert was given the WHCD gig, it was coming after a year where Laura Bush made instantly dated jokes about Desperate Housewives. The following year, the WHCD went cringe-inducingly safe as Colin Mochrie and Brad Sherwood gave us the infamous “MC Rove” bit, where the mastermind behind the Bush administration proceeded to give us some of the worst rapping this side of Kevin Federline. The point is, events like this are always teetering on the edge of “too safe” and “not safe enough,” perpetually searching for a balance that may not even exist.

But while the insurgent hosts may not please the people in the crowd, they tend to be a delight for the viewers at home. No matter how much reluctant enjoyment we get out of big flashy parties like the Oscars, it’s hard not to ignore the fact that we’re watching a room of full of rich people engage in an act of utter egotism. When a killer host comes in and takes these people to task for that egotism, it is often an immensely satisfying event. While some of the crowd at this year’s Saturday will swear that Larry Wilmore bombed, the rest of us know the truth: he was the latest person the join in the great comedic tradition of staring down some of the most powerful people in the world and making them squirm.

Larry Wilmore and the History of the Insurgent Host