Top 30 Funniest John Oliver Moments

Top 30 John Oliver Moments

Welcome to WatchMojo and today, we’re counting down our picks for the most captivating, informative, and shareable moments featuring John Oliver on “Last Week Tonight.”

#30: Trump’s Second Term
Losing his bid for re-election in 2020 did nothing to stop Donald Trump’s determination to return to the White House. In this segment, Oliver focuses on how consequential a second Trump term could be, thanks to “Project 2025” – an initiative from conservative think-tank the Heritage Foundation to reshape government. The authors, who include former Trump officials and close allies, recommend replacing thousands of federal employees with loyalists. Oliver expresses horror at both the long and short-term implications of removing checks and balances. Trump has since distanced himself from the Project, saying he knows nothing about it and disagrees with some points.

#29: Police
2020 was a watershed moment for awareness of police brutality in the United States, with the death of George Floyd at the hands of an officer sparking nationwide protests. Oliver devoted an entire show to the issue, particularly police responding to peaceful demonstrations with violence. He also focuses on the long history of racism within police departments, the difficulty of making meaningful changes, and clarifying the “defund the police” movement that was growing at the time. He wraps things up showing a powerful clip of author Kimberly Jones, speaking to just how much subjugation Black Americans have undergone for generations. Oliver is practically speechless, as are we.

#28: Tucker Carlson
One of the most recognizable figures in modern media, Tucker Carlson regularly drew millions of viewers to his Fox News program, “Tucker Carlson Tonight.” With this segment, Oliver explained precisely why that was an issue. Breaking down his tendency to make bad faith arguments, inaccurate claims, and bigoted statements, he shows why Carlson’s influence is so potentially dangerous. He also finds time for some great and very specific name-calling towards the personality. Since leaving Fox News in 2023, Tucker Carlson is arguably much less prominent than he was several years ago. But Oliver’s takedown of him still holds up.

#27: Psychics
Even if you don’t believe in the legitimacy of those who claim psychic abilities, you might think of them as mostly harmless. In this segment, Oliver explains why these supposed clairvoyants shouldn’t just be ignored as a novelty. Discussing how lucrative the industry can be and how that opens the door for people to be exploited in their most vulnerable moments, he shows how harmful they can be. He also makes it clear that his gripe is not with people who believes in psychics but those who take advantage of others for profit. Things conclude with a guest appearance from regular collaborator Rachel Dratch, playing a spoof of a certain New York-based TV personality.

#26: WWE
The world of professional wrestling is both incredibly entertaining as well as incredibly dangerous, with performers putting their bodies through serious ordeals. In this segment, Oliver focuses on the biggest wrestling franchise, the WWE, and how its stars are exploited, at times with fatal consequences. Much of his focus is on former chairman Vince McMahon and how his in-ring persona as a villain isn’t a total exaggeration. Though Oliver acknowledges that he might not strike viewers as a wrestling fan at first glance, he both highlights why its such a popular form of entertainment and why it’s so vital for those who make it possible to be treated fairly.

#25: The Monarchy
The British Monarchy is a long-standing institution whose existence many don’t think twice about. Meaning, it’s the perfect subject for John Oliver. Famously unafraid of going after his homeland, the British Oliver discusses the less-glamorous side of the Royal Family in the wake of Queen Elizabeth II’s death and Charles crowning, including their taking advantage of tax loopholes and historic ties to racism. He also debunks the idea of the monarchy as being some kind of sacred cow that shouldn’t be scrutinized. If we didn’t think he’d object, we’d crown Oliver the King of Informative Television.

#24: Subway
Though the scandal regarding spokesman Jared Fogle might be the biggest one associated with sandwich chain Subway, it’s by no means the only one. In this segment, Oliver talks about the fast food giant and the shady business practices they engage it. Key among these is how franchisees lose significant income to company-mandated fees. He even pokes fun at the shameless product placement for the chain in various media, such as in Korean drama series. In true Oliver fashion, things end with a biting spoof of one of these shows. We can always count on Oliver for some fresh satire.

#23: A History of Chuck E. Cheese
At the beginning of a segment regarding homeownership, Oliver humorously directed his under-35 viewers to go online and instead view one about Chuck E. Cheese. And this wasn’t just a tossed-off gag. Oliver devotes some 28 minutes to telling us all about the entertainment chain and its rather incredible history. Sharing clips of the original, more ornery Chuck and talking about his love for the animatronic band, he sounds more and more elated with every moment. His deconstruction of the film “Air Bud” was another clear example of Oliver’s ability to dig deep on a subject, no matter how frivolous it might seem.

#22: Environmental Racism
Oliver has a knack for showing how intertwined certain issues are, case in point: his examination of environmental racism. In this segment, he focuses on how communities of color are disproportionately subjected to pollution and other environmental hazards. With companies seemingly given free reign to contaminate these areas, with no concern for the well-being of those affected, he is justifiably outraged. The testimonials from residents put this harrowing matter into even clearer, more devastating focus. And it’s one that won’t go away unless serious reforms are made. Through this informative piece, Oliver demonstrates just how intertwined malice and indifference are.

#21: Supreme Court Ethics
The U.S. Supreme Court may try to brand itself as an impartial branch of government. But that’s not the impression many citizens have of it, especially recently. Oliver talks about how justices in the court can be easily compromised with little in the way of consequences. Much of his attention is focused on Associate Justice Clarence Thomas and the numerous gifts he’s received from wealthy donors and other clear conflicts of interest. He ends the show in amazing fashion, by offering Thomas a brand-new motor coach and a million dollars a year in exchange for leaving the Court within 30 days. Thomas didn’t follow through, but that doesn’t diminish the incredible boldness of Oliver.

#20: Dr. Oz and Dietary Supplements
One of the standout moments of “Last Week Tonight”’s first season is this segment on Dr. Oz, an accredited doctor and future Senate candidate whose hit show was considered by many in the medical community as a modern day version of a traveling snake oil salesman. John Oliver covers the doctor’s senate hearing, as well as Oz’s use of his profession to legitimize unproven products. However, the deeper focus of the editorial is the lack of regulation concerning dietary supplements, which is the result of the unbelievably legal practice of lobbying. Oliver tops the segment off by schooling Dr. Oz and the supplement industry at their own game by showing them how to pander properly, complete with puppies, t-shirts, celebrities, music, and dancing.






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#19: Tobacco
Despite its sharp decline in popularity in America, the tobacco industry continues to be profitable, thanks to emerging markets overseas. “Last Week Tonight” covers the subject, emphasizing tobacco companies’ litigation against any attempts to mitigate the marketing of their deadly products, such as the plain packaging laws in Australia, as well as poorer countries such as Uruguay or Togo, who cannot afford expensive court cases. The biggest impact of the segment, though, is the introduction of Jeff, the diseased lung in a cowboy hat, a mascot parodying the Marlboro Man. While the show sent Jeff t-shirts to Togo and put up billboards in Uruguay and Jeff appears whenever you do an image search for Marlboro on Google.






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#18: The State of Journalism
John Oliver may have said that he’s not a journalist, but he sure does care about the work that journalists do. He had already taken a harsh look at the war between advertising and news back in Season One. Then in Season 3, he devoted a segment to how corporate desire for clickbait stories was killing the viability and integrity of local news. This gave him a chance to poke fun at how clueless some conglomerates were, especially when it came to selecting their name. The bit culminated in a parody of the Oscar-winning film “Spotlight,” imagining it being set in the current journalism landscape.







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#17: Sex Education
In this piece, Oliver looks at the state of sex education in the U.S.A., with particular attention given to its inconsistency. Sex and sexuality are something most people will have to deal with at some point in their lives, and Oliver points out the absurdity of America’s varying approaches to the subject, which can range from genuinely informative to downright backwards. The editorial concludes with a simple, direct look at sex education, parodying the less than accurate sex ed videos showcased earlier, narrated by celebrities. This segment is an excellent example of “Last Week Tonight”’s tendency to highlight social or governmental issues that could use some improvement, and doing it in a way that’s enlightening and entertaining.






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#16: Alex Jones
John Oliver knows how to accept a challenge. When he poked fun at infamous conspiracy theorist Alex Jones as part of a segment on media figures that President Trump listens to, Jones dared him to dig deeper and present a more rounded picture, and that’s exactly what Oliver did. The comedian devoted an entire segment to Jones, highlighting the fact that most of his “Infowars” show is actually about selling his own line of over-priced products with dubious health benefits. Oliver even brought out his own fake doctor to endorse fake products, further mocking Jones’ questionable credentials. Sometimes, Alex, you get what you ask for.






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#15: Televangelists
While it may be hard to believe that they’re still around, the show’s spotlight on televangelists reveals that they remain fixtures of television, and wealthy ones at that. Oliver highlights the practices used by the TV preachers to get rich, with particular emphasis on “seed faith,” which is essentially asking people for money and promising good karma in return. He also illustrates the gaping tax loopholes that allow televangelists to get away with their verbal robbery; culminating with a demonstration of the process with the creation of his own short-lived real church “Our Lady of Perpetual Exemption.” The church had to close down after people got a little too literal with the “seed” metaphor.






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#14: $15 Million Medical Debt Payoff
John Oliver isn’t afraid to put his money, or at least HBO’s money, where his mouth is. To cap off a segment on predatory debt buyers and the need for regulation, he announced that he had formed a debt-buying company and bought $15 million worth of people’s medical debt, allowing him to legally demand the full amount owed. Instead, he decided to forgive all of it with the push of a big, red button. This $60,000 purchase ended up beating and almost doubling Oprah’s record for, as Oliver put it, “the largest one-time giveaway in TV history.” More importantly, it bought much needed relief for many people.






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#13: 2015 Canadian Federal Election
Originally airing the literal night before the election was due to take place, this segment focused on explaining the electoral process, while also sharing a few hilarious scandals, and detailing the major nominees for Canada’s three major political parties. Oliver pays particular attention to then incumbent Stephen Harper, whom he calls banal, but evil. The crowning jewel of the proceedings, however, is Oliver’s response to a law forbidding non-Canadians from trying to influence their elections. What follows is an over-the-top request not to vote for Harper, accompanied by music, pantomime animals, and Mike Myers dressed as a Mountie riding a snowplow.







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#12: North Korea
While “Last Week Tonight” may be famous for in-depth takes on domestic issues, Oliver proved that he can also explain and poke fun at hot-button international topics when he devoted a 2017 main story to escalating tensions between the US and North Korea. He started with President Trump's war of words with Kim Jong-un and then moved on to talk about North Korean culture and life in the dictatorship. Along the way, we learnt of the North Korean love of the accordion, so Oliver invited the most famous accordion player in America, none other than “Weird Al” Yankovic, to close out the segment with a song.






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#11: U.S. Presidential Scandals
The U.S. presidential election of 2016 dominated news for a few years and the two candidates’ major scandals are examined here in great detail. Oliver pays particular attention to Hillary Clinton’s scandals, namely her email server and the Clinton foundation controversy, explaining the complicated details in an understandable and funny way. He then contrasts Clinton’s wrongdoing with Donald Trump’s, mentioning that over 50% of the Republican’s statements were found to be false by Politifact, and that he has committed far worse, far more often, and with significantly less scrutiny than Clinton. Oliver finishes the piece off by using an incredibly effective visual demonstration of the difference between the candidates; arguing that while Clinton has more scandals than someone should, they’re nowhere near as many as Trump.






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#10: Coronavirus
When Coronavirus arrived in 2020, almost no other country in the world was hit as hard as the United States. In the beginning, Oliver was quick to criticize the American media and vague government responses to the outbreak in March 2020. While Trump and his administration downplayed the seriousness of the situation, Oliver insisted we take no chances with COVID 19, and his words have aged like milk. With the virus spiralling out of control in the US late into the summer, Oliver expanded his coverage (from home) to include the pandemic’s effects on essential workers, the unemployed, the incarcerated and the dangerous spread of coronavirus conspiracy theories.






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#9: Dalai Lama
John Oliver doesn’t do interviews that often, but when he does, he usually speaks with someone quite noteworthy. We’re talking Dali Lama-level noteworthy, or in this case, the actual Dalai Lama. After explaining the Tibetan spiritual leader’s role and the problems China is causing with his succession, Oliver played the interview he had conducted with the prominent Buddhist in exile in India. The pair touched on serious topics like Tibetans self-immolating in protest of China and the possibility of the current Dalai Lama being the last, before Oliver lightened the mood by presenting his guest with a calculator watch.






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#8: 2015 FIFA Corruption Case
Few subjects have received as many segments devoted to it on “Last Week Tonight”’s first few seasons as FIFA, the organization in charge of international football, and the corruption charges against its officials. John Oliver’s passion for the sport is really evident throughout all the coverage and the various pieces are easily some of the best the show has ever put out. Some highlights include Oliver promising to endorse products he finds gross or tacky if their companies pull their sponsorships from FIFA, which he delivers on, and his memorable feud with former FIFA vice president Jack Warner, which included purchased airtime on Trinidad TV and an announcement accompanied by dramatic music and jets of fire.







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#7: We Got Him!
Even at his most ridiculous, Oliver can be quite serious. In what became a recurring bit, he uses the comedy trope of an over-the-top though premature celebration to declare, “We got him,” when he’d catch President Trump in a lie. After the marching band or basketball-dunking tiger came out, he’d tell them to stop, because Trump was still President. This helps Oliver make the point that the benchmarks for what will end a political career keep moving, and what would have and tanked a presidency months ago won’t anymore.






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#6: Government Surveillance
Government surveillance in America is a frightening and uncomfortable subject, but also one that John Oliver handles with grace. He focuses primarily on detailing what programs like the Patriot Act allow the U.S. government to do, as well as Edward Snowden’s leaking of the information that revealed the scope of the government’s reach, while also touching on the public’s surprisingly blasé attitude about surveillance. Half of the piece’s runtime is devoted to Oliver traveling to Russia to interview Snowden himself, which made headlines around the world. Despite being a comedian first, Oliver managed to ask plenty of tough questions of Snowden, while maintaining an air of humor.






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#5: Net Neutrality
Not only can John Oliver mobilize his fans, he's also pretty good at getting those who don't like him to take action, provided they have a common interest. He proved this twice, both times with a hilarious and informative defense of Net Neutrality. After comparing putting lobbyists in charge of regulation to hiring a dingo babysitter, he challenged everyone to comment against a two-tier internet. Then, in a 2017 follow-up, he mocked FCC Commissioner Ajit Pai's jumbo coffee mug and plugged a URL that took people directly to the FCC comment page. Both times, the FCC website crashed.






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#4: Brexit Referendum
Brexit, the nickname for June 2016 referendum in which voters decided whether the UK should exit from the European Union, has been controversial and financially tumultuous. John Oliver covered his homeland’s referendum before it was actually held. In the segment, he explains the basics of what the European Union is, identifies its proponents, examines their arguments, and points out their party’s history of xenophobia and nationalism. Like many other “Last Week Tonight” stories, this one wraps up with a musical number, this time in the form of a plea for Britain to remain with the EU, while still insulting it, as sung by a barbershop quartet. It’s not often you hear young boys belting curse-laden songs about economic unions.






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#3: Prison
This early Oliver segment really set the tone for quite a few long form reports to follow. It took a serious subject, in this case, the staggeringly high rate of incarcerations in the US bolstered by the private for-profit prison system, and explored it with cold hard facts, examples of the human side of the story and, of course, the host’s unique wit. Oliver closed the segment by calling back the fact that “Sesame Street” was now talking about prison, before interacting and singing with his own version of Muppets about the topic. Informative, insightful, and funny, this bit is Oliver at his finest.






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#2: Donald Trump
While John Oliver and “Last Week Tonight” have tackled Donald Trump numerous times, this in-depth look at the then-frontrunner for the Republican Party nomination for the U.S. presidency is by far the most successful and the most biting. Oliver debunks Trump’s biggest selling points: his temperament, his honesty, and his success, none of which are as substantial as Trump claims; while also highlighting the candidate’s dangerous inconsistency when it comes to policy. However, what elevates the piece is when Oliver hits Trump somewhere he actually values: his name, which is also his brand. Oliver reveals that the alleged billionaire’s family name used to be Drumpf, a moniker that he feels is much more befitting of the ignorance, bluster, and incompetence of the man himself.






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#1: Coal
We all figured John Oliver would be sued one of these days. Oliver, though, knew exactly what bit was likely to prompt legal action, and shared that info with the audience during this segment. When talking about the bleak future for coal mining jobs in America, he brought up a cease and desist letter the show had received from Murray Energy’s lawyers and went on to talk about the company’s CEO Robert Murray anyways. Within days, Murray’s lawyers launched a defamation suit against Oliver and HBO. Apparently, the segment’s squirrel mascot, Mr. Nutterbutter, was not named as a co-defendant. Oliver went on to win the defamation case against Murray, which served as the perfect introduction for a 2019 episode on Strategic Lawsuits Against Public Participation.







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What John Oliver moment do you always return to? Let us know in the comments!