The Embarrassment of Jimmy Fallon

Donald Trump appeared on The Tonight Show and wasn’t asked a single substantive question in 10 minutes.


The Republican presidential nominee, Donald Trump, went on NBC’s Tonight Show with Jimmy Fallon yesterday. Here, in chronological order, is every question Fallon asked his guest.

—This is getting real. You still have time, do you still want to do this?

—There's kids watching at home right now ... Why should they want to grow up and be president?

—Did you always see yourself getting into politics?

—Do you think your business background helps you with campaigning?

—What has changed, from when you started running to now?

—Do you pay attention to the polls?

—You said, “If [Putin] says great things about me, I'll say great things about him.” Um?

—You say you don't traditionally prepare for the debate?

—Do you know what a coin is, by the way?

—Have you ever played the board game Sorry?

—Hillary getting sick, you handled that very well, saying you hoped she gets better. Have you gotten close to getting sick this whole campaign?

—How do you not get sick from shaking all those hands?

—I've read you eat fast food all the time?

—You're from Queens?

—Why would you excel at this job?

—How would your co-workers and peers describe you?

—What do you like to do outside of work? Do you have any hobbies?

—Why do you want to leave your current job?

—What will you do if you don't get this position?

—Could I mess your hair up?

Only twice did Fallon come even close to ruffling Trump’s feathers. The first occasion was when Fallon brought up Trump’s frequent praise of the Russian president Vladimir Putin (the candidate brushed it off as diplomacy). The second was when Fallon asked to mess Trump’s hair up. In fact, the host seemed to have built the entire 10-minute segment around an end goal of doing exactly that; all of the other questions were mere window dressing intended to lull him into a false sense of security. Fallon wanted to ruffle Trump’s hair, and ruffle it he did.

The Tonight Show with Jimmy Fallon is one of the first late-night shows that really tapped into the value of content going viral online. Surely its host thought that messing up one of the most notorious pompadours in politics would be the big takeaway of the interview—the clip that would dominate Facebook and Twitter the next morning, re-confirming Fallon as America’s premiere celebrity prankster. Instead, it’s prompted something of a backlash. In photos, Fallon rubs Trump’s head with a delighted grin, as if he’s pretending to steal dollars from his mom’s purse.

Trump has appeared on The Tonight Show before and gotten similarly soft treatment, grinning and nodding through Fallon’s cheeseball questions and gleeful impressions of the candidate. But in such a charged moment for the presidential campaign, Fallon had the opportunity to do something—anything—that could challenge the candidate. He had hundreds of different issues he could have called Trump on. He decided to mess up his hair.

Fallon is a comedian who plays it extremely safe on The Tonight Show, and his kid-gloves treatment of Trump was fairly predictable. Hillary Clinton has a similarly easy time of it on the show; Fallon has never been one to ask a celebrity a remotely challenging question, let alone a political candidate. But his platform as a beloved entertainer is a powerful one. It makes it even easier for him to ask about some of Trump’s more shocking statements without coming off as a “gotcha” interrogator. Fallon’s whole persona is rooted in empathy for his wide audience, which is especially large among younger viewers; he could have reflected that on Thursday by illuminating issues they care about.

Immediately following The Tonight Show on NBC is Late Night With Seth Meyers, a show that’s focused heavily on Trump and political humor in this election year. Talking to The Atlantic earlier this year, Meyers noted that comedians aren’t journalists—part of the fun of his show is that he can pick and choose his targets based on whatever interests, or incenses, him and his writers room. “There’s that great freedom of talking about the news without being the news,” he said. “We can just have our point of view and get it out there.”

Fallon has consistently declined to do that, and he may well think that’s contributed to his general popularity as a host. But it also contributes to embarrassments like his Thursday night Trump interview. Comedians are, after all, personalities first and foremost: Great hosts of the late-night genre like David Letterman and Jon Stewart were joke-tellers and interviewers, who couldn’t help but bring their opinions with them no matter who they were talking to. As Fallon laughed uproariously at Trump’s every line and asked about his hobbies, hopes, and dreams, it was hard not to feel like he’d missed an opportunity to distinguish himself as more than just a genial entertainer hobnobbing with the potential next president of the United States of America.