Emmys: 11 of John Oliver's Most Memorable Donald Trump Insults

1:52 PM 9/15/2016

by THR Staff

After previously insisting he didn't care about the real-estate-mogul-turned-presidential-candidate, the 'Last Week Tonight' host has repeatedly gone after the Republican nominee with witty barbs.


In 2015 John Oliver had no cares to give about Donald Trump. But by 2016, however, the gloves came off.

Once it was clear the real-estate-mogul-turned-presidential candidate was becoming a serious contender for the Republican nomination, Oliver began paying more attention to the businessman. Whether teasing his tiny hands, calling him a sociopathic narcissist, or calculating the price of his border wall, Oliver's intense dislike of Trump is entertaining to behold.

Last Week Tonight went into this year's Emmys up for six awards and last weekend won the award for outstanding writing for a variety series at the creative arts ceremony. He's still up for the big prize of best variety series talk, which will be announced on Sunday night.

Watch below to see some of Oliver's most memorable insults about Trump and Oliver telling fellow Daily Show alum Stephen Colbert, that he didn't care about the presidential candidate.

  • Oliver Tells Colbert He Doesn't Care About Trump

    John Oliver visited Stephen Colbert in October of last year and said he "couldn't give less of a shit" about Donald Trump. "It's physically impossible," he added.

    "It’s the 2016 election, and it’s 2015 right now," said Oliver, asking Colbert if they could talk about something other than the future presidential election. "So I don’t care until we’re in the same year as the thing that I’m supposed to care about.”

  • "Make Donald Drumpf Again" Is Born

    In February, Oliver dedicated an extended segment to Trump that went viral.

    "Donald Trump is America’s back mole: it may have seemed harmless a year ago, but now that it’s gotten frighteningly bigger, it is no longer wise to ignore it," said Oliver.

    "We have no way of knowing which of his inconsistent views he will hold in office," he continued. "But when he’s sworn in as president on January 20, 2017, on that day, his opinions are going to matter. And you will remember that date, because it’s the one that time travelers from the future will come back to to try and stop the whole thing from happening."

    He suggested referring to Trump as "Drumpf," citing a biographer who said that the name was once held by Trump's ancestors. Oliver trademarked the name and created "Make Donald Drumpf Again" hats

    A few weeks later he returned to Colbert's The Late Show and said even Jay Z requested a Drumpf hat and told Colbert he hadn't thought he'd have to care about Trump but "it turns out" he did.

  • Oliver Calls Trump a "Damaged, Sociopathic Narcissist"

    "Trump hasn't said one crazy thing, he's said thousands of crazy things, each of which blunts the effect of the others," John Oliver said as he highlighted what he felt was a particularly horrendous remark by Trump. Oliver was criticizing Trump's treatment of the Khan family, following Khizr Khan's speech at the DNC. He called the Republican presidential candidate a "f---ing asshole" for suggesting the reason Khan's wife Ghazala didn't speak is because she wasn't allowed to, when in fact she said it was because she was still emotional about her military son's death.

    He said Trump's insistence that he has sacrificed because he has been successful is ridiculous. "They are self-serving half-truths from a self-serving half-man who has somehow convinced half the country that sacrifice is the same thing as success," said the host.

    "Honestly, the main takeaway from these two weeks is that, incredibly, we may be on the brink of electing such a damaged, sociopathic narcissist, that the simple presidential duty of comforting the families of fallen soldiers may actually be beyond his capabilities ― and I genuinely did not think that was a part of the job that someone could be bad at.”

  • Oliver Warns Cicadas of a Trump Armageddon

    In a segment that was all about cicadas and catching them up on what has happened since 17 years ago, Oliver managed to work in a Trump dig.

    "Enjoy the world while you have the chance because, to be honest, depending on how things go in November, this planet might not be around in another 17 years," he said.

    "And I do not have time to explain that to you," he said, pointing at Trump's picture when he said "that."

  • Oliver Calls Out Trump's "Douchebag Apology"

     When a conservative radio host tried to help Donald Trump clarify his remarks on President Obama founding ISIS, Trump doubled down on his initial comments.

    “He’s so insistent,” said Oliver. "He’s like the guy drowning but waving off a lifeboat saying, ‘Get out of here, I’m very buoyant. I’m the most buoyant. Everybody talks about my buoyancy. I’m a tremendous floater.'"

    Oliver said Trump's eventual excuse of being sarcastic was "bullshit" and "the douchebag's apology."

  • Correcting "Dictator" Trump's Math

    After the Republican National Convention, Trump's campaign released a video highlighting how much applause he received during his speech.

    Oliver responded by correcting the GOP nominee's math calculation. "First, 24 out of 75 [minutes] is 32 percent not 33, but that doesn't matter," said Oliver. "The point is, the notion that Donald Trump would be a hands-off president would actually represent the best case scenario."

    He added it's much more frightening to think of Trump as "hands-on" as a leader since his speech between the applause was a "symphony of bile and race-baiting" rhetoric.

    As a bonus, Oliver unearthed an Apprentice music video, which he joked was a "warning sign" that Trump could be a dictator.

  • Oliver Suggests Waffles Instead of Trump's Border Wall

    Oliver decided to take Trump seriously on his proposal of building a wall on the U.S.-Mexico border and calculated the costs of implementing his plan.

    First, Oliver said, "The crime rates among immigrants once [in the United States] are in relatively tiny digits, which is something Donald Trump should frankly understand given that he has ten of them attached to his miniscule wrists."

    Then the host estimated that Trump’s wall would cost $77 per person and said he'd rather see people use that money to buy a waffle iron.

    "This waffle iron plan will cost less; will do nearly as much to keep out immigrants and drugs; it won’t harm our relationship with our third-largest trading partner; if it is racist, it’s only toward Belgians; and unlike Donald Trump’s wall, this makes f—ing waffles."

  • Why Trump Should Drop Out of the Election

    Oliver urged Trump to drop out and tell America his candidacy was a stunt, a "satire designed to expose the flaws in the system." 

    He added, “Just think about how triumphant it would feel to say on national television: ‘I openly ran on a platform of impossibly ignorant proposals steeped in racial bigotry and nobody stopped me. In fact, you embraced me for it. What the f— was that about?'"

    The Last Week Tonight host offered up an instruction manual at the fifth-grade reading level — a children's book called The Kid Who Ran for President. The book is about a 12-year-old boy who runs for president as a joke and wins.

    Oliver said the book even contains a speech that Trump could read if he drops out of the race, and he had Will Arnett narrate it since Oliver knows Trump isn't much of a reader.

  • 'Last Week Tonight' Invites John Miller to Make an Appearance

    When Donald Trump denied accusations that in 1991 he masqueraded as his own PR representative named John Miller, Oliver was ready to call Trump on what Oliver believed was a lie.

    The Last Week Tonight host invited John Miller to come on his show to prove his existence.

    "To be clear, this is not an invitation to Donald Trump, who has never and will never be invited here for an interview," Oliver said. He sweetened the deal by offering an overcooked steak and a hand mirror, items that Miller might appreciate.

  • Oliver Mocks Trump's Lack of Knowledge

    After Donald Trump's interview with Anderson Cooper in a CNN town hall, Oliver teased Trump for his proposed nuclear proliferation strategy. Trump said he "absolutely" would allow Saudi Arabia to get a nuclear weapon.

    "He says that with the confidence of a man who could easily find Saudi Arabia on the map,” said Oliver, “If he was given three tries and the map only included countries ending with ‘Arabia.’”

    He also joked about President Obama saying Trump doesn't "know much" about "the world generally."

    “President Obama is basically implying there that you could fill a book with the things Donald Trump doesn’t know,” said Oliver. “That book being the encyclopedia.”

  • 'Last Week Tonight' Host Compares Trump's Privates to Cheetos

    A memorable moment in the Republican primary debates this year occurred when then-candidate Marco Rubio talked about Trump's small hands and Trump defended himself and his genitalia. 

    “Donald Trump just talked about his dick during a presidential debate! A dick which I presume looks like a Cheeto with the cheese dust rubbed off,” said Oliver.

    Oliver used that as an introduction to play Morgan Fairchild reading an excerpt from Ivana Trump's romance novel.

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