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On Colbert, Hints of Hillary Clinton’s Comic Gift

When she tries too hard to be funny, she often fails—but on The Late Show, she doesn't have to be something she's not.

The Late Show with Stephen Colbert

Presidential candidate Hillary Clinton chats with Stephen Colbert on Oct. 27, 2015.

Photographer: Jeffrey R. Staab/CBS

Of all the talk shows for Hillary Clinton to appear on, there is no better forum for her than The Late Show With Stephen Colbert. One of the primary keys to Colbert’s success, both on this show and his old The Colbert Report, is that because he is such a natural and exuberant performer, he is happy to do the heavy lifting for you. David Letterman always wanted to set it and forget it, to ask a question and let the guest provide the energy. Colbert requires less. He’ll take care of all the performance: You just have to answer the questions.

Thus, a perfect fit for Clinton. A guest spot on Jimmy Fallon’s show requires her to take part in an awkward conversation with Fallon’s impersonation of Donald TrumpSaturday Night Live puts her in a well-written sketch that still makes her do a sing-along. On Ellen, good heavens, they made her do this:

Clinton, for all her practice and study, is still a good ways from being a natural performer, and she seems fundamentally unable to connect with modern popular culture. This isn’t just a factor of age, either: Back in the ‘90s, she never had the “boxers or briefs” connection with MTV and young voters; that was Bill’s job. Hillary's attempts to be cool tend to be deeply uncomfortable for everyone involved.

She’s much better just taking questions head on and playing along if she needs to, which is why her appearance on Colbert’s show Tuesday night was yet another in the string of successes she’s had over the last week. She stumbled at first, for the same reason she always stumbles on talk shows: She tries too hard to give the audience what she thinks they want. When Colbert asked her how she spent her birthday, she started off with a believable answer about taking as much time off during the day as possible in the middle of a presidential campaign, which is to say, not much. (“I slept late, that was pretty celebratory,” she said, and there are few things more relatable than having the lone sad commemoration of your birthday be one indulgent touch of the snooze button.) But then she kept going, claiming that she and Bill love to sit around and “binge-watch bad television,” which strains credulity to its breaking point. The idea of Bill and Hillary lounging in their pajamas mainlining episodes of The Good Wife for hours on end is impossible to reconcile with everything we know about both people, and Hillary trying to pretend it’s so feels, as it often does with her, like pandering.

But she recovered when Colbert started asking her questions. She’s the fifth presidential candidate Colbert has had on his show since it began, and he’s getting better and better at them: He has a way of asking tough questions we all want to know the answers to in a gentle, but pressing, fashion. And the core question, the one that Clinton has gotten so much better at answering, was, “Why are you running for president?” Her response was everything she’s skilled at: Detailed, commanding, and deeply aware of which lines, precisely, will be the most popular.

When Colbert pivoted to talk of the middle class, he even got Clinton to make a little news, saying she would let banks “too big to fail” in fact fail, if need be. She was so on her game that Colbert, after waiting for applause to die down, cracked, “That’s a cheap trick, saying things that people like.” 

It’s telling that every time Colbert tried to lead her into a joke, he steered her into shakier waters. When he joshed that he hoped a return to the ‘90s wouldn’t mean everyone will have to start wearing parachute pants, it led Clinton to say that he’d look good in those pants, and that he’s a good dancer, and don’t you agree, Jon [Baptiste, the band leader], and it threw the whole thing off. Feeling like she has to be Comedy Hillary always leads to her trying too hard, and that overeager laugh, and it throws her off her game.

Clinton is much funnier when she is being inherently truthful. Her best moment, outside of the toughness on the banks, was when Colbert asked her about Donald Trump and Ben Carson, and whether she could “picture them in the Oval Office.” She paused for a moment, thought it over and betrayed a small grin. I can picture them in some office.” That’s a good line, and it’s one she came up with on the spot. It wasn’t forced jocularity. It was just a wry little bit of truth. That’s her comic gift, and that’s what Colbert is skilled at prying out of people. For one night, they worked in almost perfect harmony. At least she didn’t have to talk to any more Trump impersonators.

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