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John Oliver, the acclaimed host of “Last Week Tonight” on HBO, has an impressive accolade track record with 21 Emmy awards to his name. Yet, he vividly recalls the numerous challenges he faced as a fledgling comedian in the United Kingdom.
Initially, Oliver opted for crowd-pleasing jokes, but he eventually shifted his focus to topics that genuinely mattered to him, such as politics. This pivot proved to be pivotal for his career. “It felt like a risk worth taking,” he reflects.
From the U.K. to the U.S.
Oliver’s comedic journey began in the suburbs of Birmingham, England, where he grew up in a family steeped in education and music—his father a principal and his mother a music teacher. As a class clown, he discovered his talent for humor early on.
At age 20, while studying at Cambridge University, Oliver ventured to the Edinburgh Festival Fringe, a renowned performing arts event that showcases a wide array of performances. This festival became his springboard into stand-up comedy. During his debut at the Fringe, Oliver was determined to give it his all.
“I remember walking offstage thinking, ‘Oh boy, I wanna do that again right now,'” he stated, emphasizing his passion for performance.
However, his early days were tough, marked by significant failures. One particularly disheartening experience occurred at a small venue called Pleasance Below, where he performed for just four people. He recalls that after some minutes, audience members gradually left, until only he and the sound technician remained. “And he said, ‘Do you wanna keep going?’ I said, ‘No, I think we’re done here,'” Oliver shared, humorously contemplating the future of his career.
Late-night in the U.S.
Oliver’s dedication to political humor ultimately led him across the Atlantic. He became an ardent fan of “The Daily Show” and, in 2006, submitted a sample of his comedy for consideration. His talent was recognized, and he quickly found himself auditioning in New York. There, he and host Jon Stewart shared laughs over a controversial hunting incident involving then-Vice President Dick Cheney, which solidified Oliver’s position on the show.
After seven successful years, when Stewart took a hiatus to focus on filmmaking, Oliver stepped in as host. He described the experience as exhilarating, likening it to taking the helm of a speeding vehicle: “Oh, pretty quick, it turns out,” he remarked.
This late-night stint caught the attention of HBO, prompting the network to allow Oliver creative freedom for his own show. He enlisted Tim Carvell and Liz Stanton, both of whom had experience at “The Daily Show,” forming a talented team. Their program was strategically scheduled for Sunday nights at 11 p.m.
“In general, it is just a rigorously researched comedy show: both because we want it to be right, and for self-preservation purposes,” Oliver stated, highlighting the need for accuracy to avoid potential legal troubles.
With a dedicated team of 83, including former journalists, “Last Week Tonight” produces 30 episodes each year. Each show begins with extensive research, often encompassing hundreds of pages, which is then distilled into outlines, scripts, and rehearsed before airing.
Oliver’s unique comedic style successfully addresses serious themes—ranging from hospice care to bail reform—finding humor in the complexities of these subjects. “I know those don’t sound funny, but it’s because fundamentally, they’re not. But there are funny things about how entrenched some of those problems are,” he explained. “And sometimes I think comedy is the best, most illuminating way to talk about them.”
To counterbalance the gravitas of these topics, Oliver likes to end each episode on a lighter note. “We love the dumb. The dumb stuff is something we all enjoy,” remarked producer Liz Stanton.
Poking fun at his adopted homeland
One of Oliver’s favorite comedic targets is American politics, particularly instances where he finds shortcomings in the system. For example, he recently critiqued Supreme Court Justice Clarence Thomas over reports of undisclosed gifts from wealthy friends, which sparked Oliver’s attention. Despite Thomas’ claims of following guidelines, Oliver humorously offered the justice a new motor coach along with a hefty annual stipend in exchange for his resignation, highlighting the need for clearer regulations in this area.
“I can prove that to you by offering this guy a million dollars a year to get the f*** off the Supreme Court. That should be a crime,” Oliver asserted, illustrating the serious implications of the lack of restrictions on judges. “The very fact that it isn’t is a problem. And that felt like the most visceral way to prove that fact.”
What distinguishes Oliver from many comedians is his deep engagement with political satire, often taking jabs at both sides of the aisle. Despite his critiques, Oliver expresses a love for his adopted home. He became a U.S. citizen, married an Iraq War veteran, and is raising two children in the United States. Addressing those who criticize his humor on America, Oliver stated, “I think you can criticize something because you love it. Because you love it and you want it to get better.”
As for his future on “Last Week Tonight,” Oliver shows no signs of slowing down. “It’s incredibly hard, not infrequently stressful, but it’s really, really fun,” he remarked. “As long as America has systemic problems, we’ll be there poking fun at them.”
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