Hillary Clinton made a joke in Iowa. It was horrible to behold. “We face a lot of evil men,” she gamely declared. “People like Osama bin Laden come to mind. And what in my background equips me to deal with evil and bad men?” There was a long pause. Mrs Clinton chortled desperately to indicate that this was, indeed, humour — a swipe, apparently, at her errant husband. There was some strained laughter from the polite voters of Davenport, Iowa, and a lot of bafflement.

The joke did not just fall flat. It bombed, leaving a vast crater of embarrassment into which the woman who would be president stared, blinking. A little later, journalists cruelly asked her to repeat the joke one more time, just to make sure they had it down correctly, and to explain what it meant. She was exasperated. “You guys keep telling me, ‘Lighten up! Be funny!’ I get a little funny and now I’m being psychoanalysed.”

I admire her for trying, and Mrs Clinton has a point. Political humour is a serious and extremely dangerous business. We expect politicians to be funny, but then savage them when the joke goes wrong. A misfired joke can wreck a political career.

Naturally funny people tend to be outsiders, misfits, tuned to the absurdities of existence and often angry beneath the surface: these are not considered ideal qualities in a politician. Sensibly, politicians usually eschew jokes; yet even the most sensible politician feels moved, in some strange lemming-like urge, to venture a joke once in a while, often with catastrophic results.

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Some of the most successful politicians have seemed to lack a sense of humour (Margaret Thatcher), but paradoxically some of the funniest people in public life have been politicians (Winston Churchill).

The word most often associated with Gordon Brown is “dour”, which is code for lacking a sense of humour. In fact Mr Brown has rather a fine, pawky Scottish wit, but he knows better than to deploy it publicly. Tony Blair is too astute to hazard many jokes, and when he does these tend to be of the familiar Les Dawson, mother-in-law, boom-boom variety. At the last Labour conference, referring to Cherie, he quipped: “At least I don’t have to worry about her running off with the bloke next door.” This is not wit, but standard musical hall fare, and safe ground. Even so, he was awarded a 17-second ovation.

John Steinbeck, writing of the Mexican revolutionary Emiliano Zapata, insisted that “Zapata had no humour. No very great statesman has ever had.” Shakespearean kings have their fools and clowns to divert the laughter away from power, yet Shakespeare has his fools speak more sense than their masters.

Mrs Thatcher made a virtue out of not getting the joke. In 1990, her speech-writers encouraged her to dismiss the new Liberal Democrat bird logo as a “dead parrot”. They showed her the Monty Python sketch. Twice. She never smiled, and at the end remarked: “Are you sure people will laugh?” Edward Heath laughed at his own jokes, loudly, with his entire body, but often alone. William Gladstone was the first Prime Minister to be mocked for humourlessness, after revealing that he read Homer for fun. (“Served him right,” said Churchill.)

This is the conundrum: politicians must aspire to humour, even if they do not have it. They must indicate an understanding of what is funny, without saying anything amusing. The 17th-century strategist Raimondo Montecuccoli advised that every leader must be “lighthearted and full of hope, by means of his facial expression . . . he should banter with his men, be clever and witty”. In other words, fake it.

Humour is risky, and preferably risqué, and the dangers are all too apparent. Siôn Simon was widely attacked for his spoof video mocking David Cameron’s home movie; the former presidential candidate John Kerry was forced into calamitous retreat after joking that school pupils who do not learn to read and write would end up on the frontline in Iraq. As Boris Johnson, the funniest MP in Britain, observed after being sacked from the front bench: “My friends, as I have discovered myself, there are no disasters, only opportunities. And, indeed, opportunities for fresh disasters.”

Aware of the looming disaster from the joke that goes awry, most politicians avoid humour, or indulge only in the most anodyne variety.

We can be fairly sure that Mrs Clinton will not vouchsafe another joke on the campaign trail, at least not in Iowa. Which is a small tragedy, for Steinbeck was precisely wrong. Some of the greatest statesmen were also genuinely funny. Ronald Reagan could be hilarious, and sometimes intentionally. He was so good at one-liners that he successfully blurred the line between real gaffes and poking fun at his own intellectual limitations: “Sometimes our right hand doesn’t know what our far-right hand is doing” is a remark of true wit.

Abraham Lincoln’s dry, deadpan humour was central to his personality. When describing his experience as a soldier in the Black Hawk War, he quipped that he had seen no “live fighting Indians but had a good many bloody struggles with the mosquitoes”. No leader has ever been funnier than Churchill: his was a spontaneous irony that never rusts, and was superbly offensive.

The second most admirable quality in a politician, after honesty, is a sense of humour. How delightful it would be if just one politician had the gumption to hoist Rory Bremner with a hoax call, but none will: jokes have become too dangerous, and the political world is poorer for that.

Have you heard the one about the funny politician? Yes, me too, but always funny peculiar, and never funny ha-ha.

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