The funniest politician in modern history

Haters and losers might object, but Trump is uniquely amusing

Donald Trump is arguably the most unsuitable candidate of any major western political party in living memory, let alone leader of its most powerful state. Brazenly dishonest at times, fond of extreme and reckless rhetoric and disdainful of most political conventions, he’s also the funniest politician in decades. 

The two things are not unconnected. Comedy as an art form has come under a great deal of strain in the past decade, a result of western society’s new moralisation. Comedians have increasingly sought to be ethical figures on the right side of a great moral struggle, ignoring the fact that funny people don’t have to be good people; indeed, some of the greatest comedians have been malicious or self-centred. 

Trump has the wit of the schoolyard tormentor, an unparalleled ability to find an opponent’s weakness. No one has coined so many unforgiving nicknames, and probably no modern figure has popularised as many phrases in the English language.

Trump originally built a following not just as a self-promoting real estate agent but also through the world of wrestling, where he perfected the art of the heel. But he famously also reached the presidency by being one of the all-time great poasters, amusing and cruel in equal measure. 

Among the phrases Trump has popularised is ‘Haters and losers’. In one of his most famous tweets, back in 2014 he wrote: ‘Every time I speak of the haters and losers I do so with great love and affection. They cannot help the fact that they were born fucked up!’ He used the phrase again the following year when he tweeted ‘I would like to wish everyone, including all haters and losers (of which, sadly, there are many) a truly happy and enjoyable Memorial Day.’

‘Many such cases’ has also become a common phrase as a result of this 2014 tweet: ‘Healthy young child goes to doctor, gets pumped with massive shot of many vaccines, doesn't feel good and changes - AUTISM. Many such cases!’

He popularised the word bigly, which was probably a mishearing of ‘big league’. GET THOSE LIGHTS OFF  has also become a meme.

‘Very very disrespectful’ and ‘Very nasty’ are also notable Trumpisms, as in ‘Barney Frank looked disgusting – nipples protruding - in his blue shirt before Congress. Very very disrespectful.’

‘Bad hombres’ is another Trump popularisation, used in one of his most controversial speeches, where he talked about illegal immigration: ‘We have some bad hombres here and we're going to get them out,’ he said, sparking off endless internet chatter.

‘Not sending their best’ is another one of Trump’s phrases that has entered common parlance, after a similarly provocative speech, about Mexicans. Despite this, Trump did pretty well among Hispanic voters in 2020.

In an even more controversial moment he called for ‘a total and complete shutdown of Muslims entering the United States until our country’s representatives can figure out what the hell is going on’. The phrase has since been mimicked and parodied a thousand times.

‘Covfefe’ was another Trumpism, after he tweeted out the typo ‘Despite the negative press covfefe’, which ended up being referenced in various television shows, appearing on T-shirts and dictionaries.

As the Washington Post recalled: ‘Personalized license plates bearing the typo were claimed across the country (but not in Georgia, where it was banned). Dozens upon dozens of applications for the word poured into the U.S. Patent and Trademark Office. Linguists sought its pronunciation. A bill in the House was named after it, as was a racehorse. The bill failed; the horse won.’

‘Who can figure out the true meaning of ‘covfefe’ ??? Enjoy!’ Trump  tweeted the next morning.

Trump’s way of talking is also funny, especially as it so lacks the sense of gravitas and normality one associates with American presidents. The video comparing Obama and Trump giving speeches after the deaths of Bin Laden and Baghdadi is especially amusing.

The full speech is here, where he announces that ‘Abu Bakr al-Baghdadi is dead,’ and as the White House official transcript records, the president declared:

It was actually — look, nobody was even hurt.  Our K-9, as they call — I call it a dog, a beautiful dog, a talented dog — was injured and brought back.  But we had no soldier injured.  And they did a lot of shooting, and they did a lot of blasting, even not going through the front door.  You know, you would think you go through the door. If you’re a normal person, you say, “Knock, knock.  May I come in?” The fact is that they blasted their way into the house and a very heavy wall, and it took them literally seconds. By the time those things went off, they had a beautiful, big hole, and they ran in and they got everybody by surprise.

Even without talking, he is visually very funny, such as in this video where he looks at a sleeping veteran.

One of Trump’s most iconic moments occurred when he wasn’t even trying to be funny. Arriving off a plane, he is told that Ruth Bader Ginsburg has died.

‘Wow. I didn’t know that. I just — you’re telling me now for the first time. She led an amazing life. What else can you say? She was an amazing woman. Whether you agree or not, she was an amazing woman who led an amazing life. I’m actually saddened to hear that. I am saddened to hear that.’

Wow. I Didn't Know That. You're Telling Me Now for the First Time has since become a meme.

As Trump exited the White House in 2021, Joan E Greve in the Guardian recorded some of his greatest moments, including the time when, in August 2017, the president stared directly at a solar eclipse, even though ‘In the days before the celestial event, ophthalmologists turned to every possible news outlet to share this urgent warning: do not stare at the sun without protective eyewear.’

There was the time when Trump yelled at a boy mowing the White House lawn, which again became a meme. Eleven-year-old Frank Giaccio had written to the president stating that he wanted to start his own lawn-mowing business, and wanted the White House as a client.

There was the weird moment when Trump touched a glowing orb in Saudi Arabia along with King Salman and Egyptian president Sisi. The time he offered to buy Greenland and retweeted a picture of how he imagined it.

Or when Trump asked seven-year-old Collman Lloyd whether she still believed in Father Christmas. She had written to the North American Aerospace Defense Command to track Santa’s whereabouts in 2018, and ended up talking to the president by phone, who asked: ‘Are you still a believer in Santa? Because at seven it’s marginal, right?’