The Shady Side Of John Oliver Everyone Ignores

With his current show boasting over ten seasons and dozens of Emmy Awards, John Oliver has become a household name — especially since he officially became an American citizen in 2019. With each new season of “Last Week Tonight” covering wide and niche topics, it seems Oliver is enshrining himself as a beloved host and occasional voice actor. Surviving multiple writers’ and actors’ strikes throughout his storied career, it seems Oliver always comes out on top. However, there’s more to the comedian than meets the eye.

There are many little-known facts about John Oliver that may surprise even the most loyal of his viewers. While the funny man has done an excellent job at keeping his nose clean, there are still some controversies that may have gone under the radar. Whether he’s made some guests uncomfortable or gone too far in his on-screen pranks may be in the eye of the beholder, but there are some shady things about John Oliver that fans certainly overlook.

When Donald Trump first took office in January 2017, it was fairly obvious he was getting his big ideas from the friendly faces at Fox News. In an effort to combat this, and possibly provide Trump with a quick education on the matters at hand, John Oliver and the team behind “Last Week Tonight” bought ad space on the local Washington, D.C. channels they assumed Trump would be viewing. In the ad, a folksy older gentleman in Western attire, fondly referred to as the Catheter Cowboy, starts discussing pain management needs before diving into the political fray.

What started as a brief rundown of the nuclear triad in a 40-second ad in February of 2017 eventually morphed into a compelling call to convince Trump not to end the Iran nuclear deal by April 2017. While it is a commendable way to subvert the chain of command to gain an audience in front of the president, the use of something as clinical and intimate as a catheter to get attention might have rubbed some the wrong way. This is an indication that Oliver is willing to get shady to prove a point.

In 2018, when then-Vice President Mike Pence announced his family had written a children’s book, John Oliver took it as a challenge. Pence, known for his incredibly conservative views — especially towards the LGBTQ community — was promoting a book written by his daughter, Charlotte Pence, and illustrated by his wife, Karen Pence. Ever the one-upsman, Oliver and his writing team hopped on the opportunity to not only parody the book but beat the Pences to the punch.

Pence’s book, “Marlon Bundo’s Day in the Life of the Vice President,” followed the Pence family pet, a rabbit named Marlon Bundo, throughout a wistful day in the White House. “Last Week Tonight” staff writer Jill Twiss authored a parallel version of the children’s story, titled “A Day in the Life of Marlon Bundo.” In Twiss’s version, Bundo has a same-sex romance with another male rabbit, making a point to call out Pence’s opposition to gay rights.

“A Day in the Life of Marlon Bundo” hit bookstores a day before the Pence family’s books did — with Oliver highlighting the release on the coinciding episode of “Last Week Tonight.” The book absolutely blew the Pence competition out of the water — becoming a bestseller on Amazon overnight. All profits from the book have been donated to The Trevor Project and AIDS United.

In 2017, John Oliver took to “Last Week Tonight” to point out the extreme callousness of the coal industry — taking particular aim at then-CEO of Murray Energy, Bob Murray. Murray slapped Oliver and his show with a lawsuit as he took issue with some of the more colorful language Oliver used to describe him. Murray claimed in the suit that “nothing has ever stressed him more than this vicious and untruthful attack,” according to The Guardian. Oliver responded by admitting that’s “an odd thing to say, given that … [Murray] oversaw a company whose mine collapse in Utah resulted in the deaths of nine people.” Part of the suit included the fact that Oliver couldn’t discuss the case — or Murray — in any capacity during litigation. So, it took until 2019 for Oliver to fill us in on the end result.

The lawsuit was initially dismissed by a West Virginia court, which Murray appealed before dropping it entirely. The timing of this coincided with Murray Energy filing for bankruptcy. After Murray dropped the suit, Oliver was able to hop back behind the desk and point out that these types of lawsuits are meant to “put the defendant through a difficult, painful experience.” Having the privilege of the platform HBO provides him, Oliver also took the opportunity to once again taunt Murray on behalf of the little guy — ending his follow-up episode with a reminder that he will always be willing to advocate, “not just on our behalf, but on behalf of every small newspaper and individual [Murray] has sued.”

The year 2017 was tumultuous for John Oliver, or at least, Oliver was determined to make it one. While Oliver was moderating a panel discussion with acclaimed actor Dustin Hoffman for an anniversary screening of “Wag the Dog,” Oliver purposefully made things awkward. John Oliver called out Dustin Hoffman over a sexual harassment allegation, and Hoffman gave a lukewarm response. For his part, Hoffman attempted to push back, which only set Oliver up to dig in deeper.

According to The Washington Post, Oliver made a point to bring up the allegations against Hoffman, saying, “I can’t leave certain things unaddressed. … The easy way is not to bring anything up … no one stands up to powerful men.” In response, Hoffman snarked, “Do you believe this stuff you read?” To which Oliver responded, “Yes … because there’s no point in [an accuser] lying.” This obviously got under Hoffman’s skin, rankling the actor. However, even in their back and forth, Hoffman still didn’t really acknowledge or apologize for any of his alleged previous behavior. Oliver’s efforts to at least discuss the claims of harassment are commendable and maybe even paved the way for producer Wendy Riss Gatsiounis to come forward with her own complaints against the “Kramer vs. Kramer” star.

Hailing from the United Kingdom has afforded John Oliver a unique perspective on the royal family. In an eerie way, it almost seemed as if Oliver predicted some of what would happen to Meghan Markle. In a 2018 interview on “The Late Show With Stephen Colbert,” Oliver said of the royal family, “They’re an emotionally stunted group of fundamentally flawed people doing a very silly pseudo-job. That’s what [Meghan’s] marrying into.” It seemed like Oliver was reading the tea leaves when he also mentioned that he wouldn’t “blame her if she pulled out of this at the last minute.”

After Meghan Markle and her husband, Prince Harry, stepped down from royal duties and relocated their small family to the United States, the couple gave a bombshell interview with Oprah. Oliver’s snarky prediction turned out to be correct in how Markle was ultimately treated. In 2021, Oliver appeared on “The Tonight Show” with host Jimmy Fallon to discuss what Oliver found surprising about Oprah’s interview with Markle. “I know the royal family from a distance, and they seem like flawed people. That’s literally the kindest way I could possibly put it.”

While criticizing the royal family might not seem like the biggest deal stateside, it still proves that, once again, John Oliver is willing to get messy to speak truth to power – no matter how many lawsuits it entangles him in or how many stars he makes uncomfortable along the way.