Bruce Cherry swears George W. Bush is funny.
"Bush is perfect for comedy," he told me. "He knew how to pause and deliver a line. He's actually good. He's just a natural."
Cherry would know. He's a committed liberal, but he's written comedy material for Bush at such prestigious events as the White House Correspondents' Dinner and the Alfalfa Club, an annual gathering of the most powerful political movers in DC.
No one votes for a candidate just because they're funny—Al Franken didn't win his Senate seat based on his Stuart Smalley material. But telling jokes can demonstrate charm, charisma, and likability. It can make a politician seem almost human. And that's where writers like Cherry come in.
"Everyone wants to be able to tell jokes. And if someone can't be funny we think less of them," Cherry said. "If someone can be funny, it's impressive; you think that person can think on their feet. It's a skill."
Cherry got his gig with George W. Bush after writing material for a Bush impersonator named Steve Bridges. "Barbara Bush saw him at an event and loved him so much that she told George," Cherry recalled. Bush and his doppelganger appeared together on stage at the 2006 White House Correspondents' Dinner, and Cherry was one of the team of writers in charge of the duo's material.
"Conservative audiences loved dumb George Bush jokes," Cherry said. "George Bush loved them!" The writer's favorite was actually delivered by Jeb Bush at an Alfalfa Club dinner: "George told me he's thinking of running again. I said, 'George, the Constitution prohibits you from running for a third term.' He said, 'Wow, they put my name in the Constitution!'"
That sort of self-deprecation can be freeing. "What I liked most about writing for politicians was pushing out the parameters of what they were able to say in public," Mark Katz, who injected humor into Bill Clinton's speeches during his eight years in the White House, told me. "Being part of the best strain of our political dialogue where politicians are telling more truths—saying the things using humor that they would otherwise strenuously deny the other 364 days of the year."
Katz went on to found the Soundbite Institute, a think tank predicated on the idea that humor is a necessary weapon in any politician's arsenal. "Jokes is the actually the wrong idea," he tells me. "It's really about what's the idea for the speech. What does the speech need to be? And then comes the jokes. Jokes are an execution—but the speech needs to be ideas."
A case study Katz loves to cite is a Clinton line from the 1993 White House Correspondents' Dinner. The president had had a rough 100 first days in office, and he didn't avoid the elephant in the room. The Katz-penned line was: "I don't think I'm doing that bad. After this point in his administration, William Henry Harrison had already been dead for 68 days."
"After the laughter receded, this lesson remained: Humor is a persuasive and underutilized tool in the realm of strategic communications" is how the Soundbite website describes the lesson from that moment.
"Humor flatters where spin insults," Katz told me. "It's a signifier of intellectual honesty. If this person is being honest with himself—then I trust this person to be honest with me.
"There are people I know who would unfriend me if they knew I've written for Bush," Cherry said. But he wasn't going to say no. "He is the President of the United States. And I am an American—so fuck it. I'm definitely not going to turn that down," Cherry added. "It's not like I'm moving his Iraq plan forward—I'm just letting him tell a few jokes." (He said he did refuse writing gigs from Rick Santorum and Mitt Romney, even though the money being offered was "insane.")
"In the White House there are maybe ten people who can write a joke—and there are 250 people who can kill a joke."
Sometimes, a politician doesn't need a team of writers to defuse a situation with a joke—recall Barack Obama saying, in a 2006 interview, that he "inhaled" marijuana when he was young because "that was the point."
But even when a statesman does have funnymen on hand, any joke has to be in the speaker's voice. Katz will invariably ask a politician to take a joke out of their speech if they're not completely sold on it. "I know if they don't believe in it—it's not going to work," he said. "Until you believe in a joke, you really should not say a joke out loud."
Katz had dozens of meetings with Clinton to go over every draft he prepared and the president would then select the material he thought would work best. When you're the leader of the free world, there are lots of things you can't say, even in jest. "In the White House there are maybe ten people who can write a joke—and there are 250 people who can kill a joke," Katz said. "So you're trying to get a speech through that gauntlet—that's the real challenge."
Material is one thing, delivering laughs another. Katz coached former United Nations Ambassador Madeline Albright by bringing in a professional standup comedian and having her listen to his comedic cadences as he read the material.
"Here's someone who speaks six or seven languages—she can pick up a cadence," Katz said.
Both Cherry and Katz said Obama has great natural comedic timing. "He pauses anyway, and that works really well if you're doing dry humor, which is the stuff they give him," explained Cherry. "It's very thoughtful and works out perfectly to the way he talks."
Katz agrees, but thinks Obama has found his true comedic voice only recently. "For a while, my critique of Obama was he looked like a guy who was really enjoying himself immensely as he read off a bunch of really funny jokes his staff had written for him," Katz said. "But it did not sound like his voice to me."
Obama's two potential successors had to put their own comedic chops on display at last month's Al Smith Dinner in New York. Katz said that Hillary Clinton should have been a little more self-deprecating. "I would have crossed out all but two or three of the jokes at Trump's expense," he told me. "To me, making fun of him at this point, is like poking a bear in a cage; it's practically beneath us. To try and provoke him, to me, is borderline cruel at this point."
"She's going to learn that conceding more brings bigger dividends," Katz added.
Trump, meanwhile, simply died onstage, and even got booed when his jibes turned into humorless insults.
"That's the worst I've seen a politician bomb," said Cherry. "He's not funny, he's just mean. That's what sells him. People who want mean like him."
"Trump has thrown out the entire political playbook as it existed before 2016," said Katz. "And humor is in that playbook. Nothing that he does corresponds to the standard operational procedure of using humor to win and influence people."
Trump's interpretation of humor, as Katz sees it, fails in all aspects of the effective political paradigm. "There's nothing kind. There's nothing self-defacing. There's nothing self-directed. There's nothing honest." His jokes "exist to hurt. So humor is probably the wrong word for it."
Follow Harmon Leon on Twitter.