Comedians Still Don't Know How to Make Trump Funny

Jordan Klepper remembers a time when Donald Trump's rallies were fun for him. The Daily Show correspondent began going to candidates' events during primary season, and in the beginning, the alleged billionaire' supporters were excited for a chance to be on TV and conspiracy theories were still fringe enough to be fresh. Over the course of several months, Klepper's segments, called Jordan Klepper Fingers the Pulse, featured man-on-the-street style interviews that he described to me as both "hilarious and terrifying"—two qualities he doesn't consider mutually exclusive. But at some point, he says, absurdity and paranoia became commonplace.

"Near the end of the campaign, people started following us around thinking we were from inside the government or working for Hillary," Klepper told me. "People were googling things on the back of our battery packs thinking we were the CIA."

The Daily Show wasn't the only comedy program to put a man on the ground at a MAGA event. In September 2015, a year before Klepper started his series, a correspondent from Jimmy Kimmel Live! got an older woman to chant "DTF" on camera because she thought it stood for "Donald Trump forever."& Eric Andre, whose brand of comedy can approach performance art, went to a pro-Trump event at the Republican National Convention and wound up on stage next to conspiracy theorist Alex Jones. Other shows tried integrating Trump himself into their programs, with mixed results: SNL had him on as a host (he bombed), and Jimmy Fallon playfully tousled Trump's hair, then got roasted for it.

Trump unquestionably does big numbers for NBC, and the president-elect's feud with SNL has given the show new relevancy. But though Tina Fey once quipped that Trump's campaign was "good for comedy," it seems like the opposite turned out to be true. Mocking Trump's supporters can seem cruel, joking around with Trump a la Fallon can make a comic seem in cahoots with Trump, and how do you parody a moment it political history that already seems straight out of an implausible satire?

On the week of his inauguration, it doesn't seem as if people have figured out the right way to make a joke out of a joke, or to least produce intelligent commentary that doesn't reinforce the strict ideological and cultural silos that got us here in the first place.

Writing for the Columbia Journalism Review last month, the critic Lee Siegelargued that Stephen Colbert and Jon Stewart helped create the culture of fake news that led to Trump's rise—that "truthiness" gave way to the post-truth era. His point seems to be that they too often blended real commentary with satire, and that Americans eventually learned to forget the difference. But Sophia McClennan, a professor of comparative literature at Penn State vehemently disagrees, so much so that wrote a book called Is Satire Saving Our Nation?: Mockery and American Politics and another entirely about Colbert.

"One of the things that satirical comedy does is provide you with a shared vocabulary and language and a way of processing something," she told me. "And research has shown that satire lights up the brain. If they plug you in, and you watch a news report and then a satirical news report, your mind is working harder. So we know it's good for us when things have become overly simplified and extreme and we're definitely gonna need satire in the Trump era, it's just gonna be tricky."

Klepper's Daily Show segments aren't overtly satirical, but they do contain some elements of the style. In one, a man stands next to his daughter while claiming he wishes he could grab women by the pussy like his preferred candidate. It's not exactly laugh-out-loud funny but technically works because of dramatic irony—the dude doesn't seem to understand the cognitive dissonance the viewer experiences or the discomfort it induces.

The strategy of letting Trump supporters hang themselves is a tactic also used by former Late Night with Seth Myers writer Conner O'Malley. He doesn't consider himself a satirist—"although if there's a message, great," he told me. His character of Mark Seevers from TruthHunters.com was invented last February when he attended the anti-Beyonce protest at the NFL headquarters in New York, honed at a Trump rally in Orlando in March, and perfected during the Republican National Convention, where a BBC journalist interviewed him thinking he was for real.

Later, when the Cubs made their World Series run, he took on the role of an alpha-male mega-fan who gets mad when people don't want to drink as much as he does, reads Tucker Max,and thinks that "Donald Trump is pimp." O'Malley says that he's always enjoyed doing comedy about conspiracy theories and aggressive masculinity—meaning he didn't set out to do political bits, but rather politics suddenly appeared in the space his comedy occupied.

"I grew up with a lot of brothers and everyone in my family is like an elevator mechanic, or a carpenter, or an electrician—a masculine, blue-collar family," he told me. "I feel like if I made three different decisions in my life I would be similar to those characters that I play, but I almost accidentally found a comedy community and different people in it who are from different parts of the world and introduced me to different ideas."

Unlike O'Malley, Lee Camp, the 36-year-old behind RT America's Redacted Tonight very much considers himself an activist. Although he started off as an admirer of George Carlin and Mitch Hedburg, he drifted toward politics as a result of the Iraq War. Today he considers himself "a comedian first, but only by a couple of feet" and is basically an angrier, more stridently left-wing version of Jon Stewart. (RT, formerly Russia Today, is funded by the Kremlin and featured pro-Trump programming, though Camp himself has used his show to attack Trump.)

While Stewart went on hilarious rants about trivial Trump stuff five years prior to his presidential bid, Camp says he didn't want to give the man free publicity. Today, he even shies away from making golden showers jokes on his show, figuring that everyone in America has already made those same jokes around their dinner tables.

What's more, Lee differs from his comedy-meets-news predecessors by not belonging to either party. His fans don't necessarily agree with him politically, he says, which is what makes his comedy effective in influencing public opinion. One example he likes to give is of a viewer who generally agrees with his stances, but differs in support of the death penalty.

"If I do a joke and include how the number one determinate in equal trials of whether someone gets the death penalty is race of the victim, they may keep supporting the death penalty they've got that fact," he told me. "They know the death penalty is racist—at least in the way that we do it now—and hopefully over time that impacts them and how they feel about that."

In the burgeoning Trump era, comedians have to strike a tricky balance. Satirists are tasked with the seemingly impossible task of using sarcasm and snark to enlighten a populace who can't differentiate between fact and fiction. And comedians of all stripes have to work out how to talk about politics—make fun of both sides and get accused of false equivalence? Or go full anti-Trump and become an outright partisan?

Steve Bodow, the executive producer for the Daily Show and its former head writer, says he's up to the challenge. Although the show's audience obviously skews liberal, he thinks it's necessary to keep them on their toes. He says that, for instance, when Meryl Streep gave her anti-Trump speech at the Golden Globes and criticized people who watch football and mixed martial arts, it struck people in his writer's room as tone deaf.

Although he doesn't want the liberal media to think of his show as gospel, he admits that his writers don't have to try as hard to take a whack at the kind of person who attends a Trump rally and rattles off about birtherism and pussy grabbing. In fact, they don't even have to try at all—Klepper just has to hold up a mic and give them their 15 minutes.

"I think that they're not in any way ashamed of what they think, so what's to be embarrassed about?" he told me. "If we smart-ass liberals happen to think it's ridiculous, that's our problem. And at the current moment, they've been proven right."

Follow Allie Conti on Twitter.