Why Donald Trump remains the funniest politician in modern history

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 moralization. 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-centered. 

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 popularized 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 posters, amusing and cruel in equal measure. 

Among the phrases Trump has popularized 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 popularized 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 popularization, 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 [covfefe] 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?”

Then there are Trump’s various insults, which the failing New York Times has catalogued, and which shows his penchant for nicknames to be unsurpassed. As well as Crooked Hillary,  former US Senator Jeff Flake was “Jeff ‘the Flake’ Flake,” or “Jeff Flake(y).” Nancy Pelosi, former Speaker of the House, was “Crazy Nancy,” Joe Biden was ‘Sleepy Joe’ and Elizabeth Warren, who had claimed to be partly Native American, was “Pocahontas.” Trump stated that “Her false claim of Indian heritage is only selling to VERY LOW I.Q. individuals!”

He described his 2016 rival as “Jeb ‘Low Energy’ Bush,” a “failed presidential candidate,” and on one occasion taunted that he “just got contact lenses and got rid of the glasses. He wants to look cool, but it’s far too late.”

Beto O’Rourke was “Dummy Beto,” Bernie Sanders “Crazy Bernie,” Congressman Adam Schiff was “Shifty Schiff” and Senator Chuck Schumer, “Cryin’ Chuck Schumer.” Alexandria Ocasio-Cortez was “dumb as a rock AOC” and “a Wack Job,” while he called Kamala Harris “a gaffe machine” and “a super liberal wack job that NOBODY wanted!”

Anthony Scaramucci, who was White House communications director for eleven days under Trump, was a “lowlife loser” and “a highly unstable ‘nut job,’” a “mental wreck” who over “eleven days of gross incompetence made a fool of himself, bad on TV.” Political strategist Steve Schmidt was “a blathering idiot,” while he taunted Dr. Anthony Fauci, head of the Covid Task Force, on his baseball throwing, tweeting “Bad arm!” and he “threw out perhaps the worst first pitch in the history of Baseball!” but that “Tony’s pitching arm is far more accurate than his prognostications.”

He’s also had several rows with foreign politicians. He described Gustavo Petro, future president of Columbia, as “a major LOSER” and called Kim Jong-un “Little Rocket Man,” and “obviously a madman,” and once tweeted that “I would NEVER call him ‘short and fat.’” In a famous foreign policy declaration, the US president tweeted: “North Korean Leader Kim Jong Un just stated that the ‘Nuclear Button is on his desk at all times.’ Will someone from his depleted and food starved regime please inform him that I too have a Nuclear Button, but it is a much bigger & more powerful one than his, and my Button works!”

Syria’s leader was “Animal Assad,” and he tweeted that Iran’s Supreme Ayatollah Ali Khamenei “has not been so Supreme lately,” and “He should be very careful with his words!”

Despite his taunts, Trump employed a relatively non-confrontational foreign policy, resisting the urge to escalate with Iran. Trump is as disdainful of the neocons as he is of the Republican establishment more generally, and described neocon diplomat John Bolton, who he hired and then fired as a national security advisor, as “one of the dumbest people in Washington,” “so stupid,” “A real dope!,” “Wacko,” “dumb warmonger,” “one of the dumbest people I’ve met in government and sadly, I’ve met plenty,” a “lowlife dummy,” and “Washed up Creepster.” Bolton, Trump said, “added nothing to National Security except, ‘Gee, let’s go to war.’”

In his assessment of the neocon attitude to foreign policy, he wasn’t far off, and Trump often gets things right, perhaps because his narcissism makes him almost immune to the status-signaling and conformity that leads to groupthink. In 2018 the German delegation at the UN laughed at the US president because of its criticism of an energy policy which made them dependent on Russia. All right-thinking people laughed along with the Germans, because that’s the socially correct thing to do, even though Trump was clearly accurate. Despite this, the midwits haven’t learned their lesson.

He also described Germany as “a total mess-big crime,” and “going through massive attacks to its people by the migrants allowed to enter the country,” which is not untrue. Similarly, his comments about “shithole countries” were indelicate and rude, and attracted commentary with was more interested in pity than truth.

Trump is especially scathing of journalists, who largely hate him almost to a demented degree. You might say it’s because they’re truth-seekers who are shining a light on an especially corrupt politician, or because they’re partisan scolds who see their job as America’s new moral leaders. Both are true, which makes his insults both funny and disconcerting.

He described Politico as being “in total disarray,” “going out of business” and “Losing too much money. Great news!” He called the Atlantic a “failing Radical Left Magazine,” “boring but very nasty,” and “rapidly failing, going down the tubes.” The “Gray Lady” he called ‘the failing New York Times’ while the Washington Post “shouldn’t even be allowed on the grounds of the White House because their reporting is so DISGUSTING & FAKE.”

Although routinely abusing journalists personally, his list of insults aimed at Mika Brzezinski, co-host at MSNBC Morning Joe, was especially extensive: “ditzy airhead,” “wacky,” “Crazy Mika,” a “very angry Psycho,” “dumb as a rock,” “low I.Q.,” “off the wall,” “neurotic,” “not very bright,” a “mess!,” “very insecure,” a “clown,” and “had a mental breakdown while talking about me.” Quite clearly, he never thinks about her at all.

On one notorious and bizarre occasion, Trump retweeted AI wrestling footage of him beating up a CNN reporter. The channel contacted the man who created the video and, presumably aware that the media would probably dox him and ruin his life, he apologized.

Trump often gets things right, perhaps because of his narcissism

The moralizing tone of some journalists only makes Trump funnier. During the start of the pandemic, when the media was going through one of its piety frenzies about racism and prejudice being worse than the disease, Trump insisted on calling it the “China virus,” saying on one occasion: “All over the World the CoronaVirus, a very bad ‘gift’ from China, marches on. Not good!”

There were plenty of celebrity spats too. He called Bette Midler a “Washed up psycho” and “a sick scammer.” Of basketball player LeBron James, who was critical of Trump, he tweeted: “Lebron James was just interviewed by the dumbest man on television, Don Lemon. He made Lebron look smart, which isn’t easy to do. I like Mike!”

He described Robert De Niro as “a very Low IQ individual,” suggesting that he “has received too many shots to the head by real boxers in movies. I watched him last night and truly believe he may be ‘punch-drunk.’” He added a second tweet with “Wake Up Punchy!”

Trump has also consistently provoked the ire of major corporations, many of which criticized his immigration restrictions, including Budweiser and Airbnb. When Coca-Cola became involved in this “CEO activism,” Trump replied, “that’s okay, I’ll keep drinking that garbage.”

Trump has also inspired huge amounts of art. There was the picture of Jesus by his side in court, which he retweeted (obviously), and images of Christ guiding his hand in the Oval Office. Trump even hung a painting of himself sat with former US presidents in his office. In a world where kitsch is the most low-status signifier in cultural tastes, it’s all part of the fun, his taste in art reminiscent of Dogs Playing Poker or Viz’s The Life of Christ in Cats.

Since Trump’s defeat in 2020, and the subsequent unrest the following January 6, the comedy had grown darker. He was banned from Twitter, but a few weeks later emailed an Easter Message “TO ALL. including the Radical Left CRAZIES who rigged our Presidential Election, and want to destroy our Country!”

Trump’s posting skills have declined a fair bit, although no one could maintain that quality for so long. Although his Twitter ban was rescinded by Elon Musk, he largely sticks to his own right-wing troglodyte ghetto, Truth Social, where his posts — stating his petulant hatred of Taylor Swift or rants about communists — are nothing on his old hits. But he still makes the odd funny speech, such as his recent monologue on whether it was better to be electrocuted or eaten by a shark.

He is still amusing when apologizing for a severe combover, joking about his assassination attempt or boasting about how much electricity there will be under his presidency. Indeed there will be so much that “you’ll be saying, please, please, president, we don’t want any more electricity. We can’t stand it. You’ll be begging me. No more electricity, sir. We have enough. We have enough”

Haters and losers and Radical Left CRAZIES might disagree, but he remains the funniest politician of our age.

This article was originally published on Ed West’s Wrong Side of History Substack.