The annual dinner hosted by the White House Correspondents’ Association, in Washington, is traditionally an occasion when the US president is lampooned and ridiculed to his face, and is expected to take the ribbing in good part.

So Donald Trump’s decision to boycott this year’s event looks like a serious sense of humour failure, indicative of his rapidly deteriorating relationship with the media.

But Trump is by no means the first American leader to fall out with the press and fail to see the joke. Thomas Jefferson, the third US president, complained bitterly about what would now be called fake news, a subject close to Trump’s heart. “Nothing can now be believed which is seen in a newspaper. Truth itself becomes suspicious by being put into that polluted vehicle,” Jefferson wrote in 1807.

Luckily for him, perhaps, Jefferson did not have to break bread with journalists in front of television cameras. The WHCA was not formed until 1914 and its annual dinners began in 1921. But age-old tensions were not dispelled.

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In 1913, Woodrow Wilson had threatened to scrap presidential news conferences after complaining that “certain evening newspapers” had quoted remarks he considered off the record.

The founders of the WHCA issued a binding code of conduct for reporters to reassure Wilson and persuade him to keep the White House doors open. Wilson relented but, like Trump, he heartily disliked press conferences, which he thought a tedious waste of time. He stopped holding them altogether in 1915.

Although notorious for their funny and satirical speeches, these White House journalists’ dinners often carry a sharp political edge. Richard Nixon, who famously blamed hostile hacks after a 1962 election defeat in California, saying “you won’t have Nixon to kick around any more”, skipped the event entirely, back in 1972.

During the Watergate scandal that brought him down, a besieged Nixon told advisers: “The press is your enemy. Enemies. Understand that? … Because they’re trying to stick the knife right in our groin.” His comments find an echo, decades later, in Trump’s repeated description of the media as the “enemy of the people”.

Ronald Reagan did not attend the dinner in 1981, after being badly wounded in a roadside assassination attempt. But he gamely phoned in from Camp David instead. “If I could give you just one little bit of advice, when somebody tells you to get in a car quick, do it,” he joked. Reagan, known as the Great Communicator, added: “Well, I’m looking forward to the next news conference. I have so many questions to ask you all.”

Bill Clinton always liked a party and attended all eight dinners during his two terms as president. He usually kept his cool. In 2000 he said he forgave the jokes made at his expense by the comedian Jay Leno: “Me and Leno, we give hope to grey-haired, chunky, baby-boomers everywhere.” But Clinton, too, railed against the media at other times, once publicly condemning “purveyors of hatred and division” on the public airwaves.

George W Bush, himself a noted practical joker, got it in the neck from the comedian Stephen Colbert in 2006, who ruthlessly parodied his “no fact zone” philosophy of government, especially in Iraq. He likened him to Sylvester Stallone’s fictional boxer Rocky Balboa whom everyone wanted to punch in the face. Bush took it on the chin.

Some of the harshest treatment in recent years was dealt out by the comedian and writer Seth Meyers, who went after Trump at the 2011 dinner. Meyers likened Trump’s appearance to an “old rusty bird cage”, saying the billionaire preferred Fox News because he wore a fox on his head. He predicted Trump “running as a Republican” in 2016 would be more like “running as a joke”. Funny, but wrong.

The other person to needle Trump in 2011 was, of course, Barack Obama, who used the WHCA platform, year in year out, to display a masterly mix of self-deprecation and shrewd mockery of the media.

At the height of the so-called birther controversy – Trump’s questioning whether or not Obama had been born in the US – the latter noted that Trump was among the dinner attendees at the 2011 event, and said: “I know that he’s taken some flak lately, but no one is happier, no one is prouder to put this birth certificate issue to rest, and that’s because he can finally get back to focusing on the issues that matter, like did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?”

The WHCA dinner, known inside the Beltway as the Nerd Prom, has been criticised in recent years for encouraging unseemly cosiness between independent media and those in power. Some news organisations, such as the New York Times, no longer attend. Guardian US made it clear last month that it would not be attending this year’s dinner.

Problems with over-friendliness seem unlikely to recur in the Trump era. With the president finding the after-dinner jokes hard to swallow and taking himself off the menu in April, there are now suggestions his spot should be taken by the actor Alec Baldwin – the merciless, orange-faced, late-night TV impersonator of Trump.