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Top 20 John Oliver Moments

Top 20 John Oliver Moments
VOICE OVER: Rebecca Brayton
These John Oliver moments left us all wiser. For this list, we'll be breaking down the funniest, most memorable and culturally relevant segments from the HBO news satire program. Our countdown includes the state of journalism, we got him, Donald Trump, and more!

Top 20 John Oliver Moments


Over the last decade, this British host and comedian has become a mainstay of both journalism and comedy. Welcome to WatchMojo, and today we’ll be taking a look at our picks for the Top 20 John Oliver Moments on Last Week Tonight.

For this list, we’ll be breaking down the funniest, most memorable and culturally relevant segments from the HBO news satire program.

#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 whose hit show is 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.

#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.

#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.

#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.

#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.

#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.

#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.

#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.

#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.

#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.

#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.

#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.

#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.

#7: We Got Him!


Even at his most ridiculous, Oliver can be quite serious. In what is becoming a recurring bit, he uses the comedy trope of an over-the-top though premature celebration to declare, “We got him,” when he catches President Trump in a lie. After the marching band or basketball-dunking tiger come out, he tells them to stop, because Trump is 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.

#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.

#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.

#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.

#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.

#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.

Before we unveil our top pick, here are a few honorable mentions:

Wealth Gap

Police Brutality

Miss America

Catheter Ad

#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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