John Oliver on Monday said the "funniest" response the Emmys could have staged when Stephen Colbert won Outstanding Talk Series would have been an unexpected winner — a quip delivered during an interview with Jimmy Kimmel.
Oliver, who has won Emmys for his show "Last Week Tonight," said during the appearance that while "the right thing to happen was for him to win," the most amusing outcome would have been if Kimmel had taken the prize. "I will say this — I know we wanted him to win. The right thing to happen was for him to win. The funniest thing to happen would have been if you had won," Oliver said. Kimmel replied that most of him hoped Colbert would prevail but admitted a private, mischievous urge to see the stunned look on his own face.
Kimmel also recounted an improbable moment of confusion when a driver for one of his writers used ChatGPT to check who had won the Emmy. The driver, Kimmel said, received an incorrect result claiming Kimmel’s show had won, and briefly questioned whether the AI knew something the live audience did not. "I was like, ‘Oh shit! If we win, this is a disaster!’" Kimmel said. Oliver added that had an erroneous announcement occurred, the fallout backstage — with Kimmel and his staff present — would have been chaotic. "You’d have been booed onto the stage," Oliver said.
Oliver said he cut short an interview to watch Colbert deliver his acceptance speech and that those backstage were "all very happy" for him. In the speech, Colbert said he had never loved his country "more desperately" and urged Americans to "stay strong" and "be brave." The remarks followed weeks of speculation about the motivations behind CBS’s decision to cancel Colbert’s late-night program, a move the network said was a financial decision.
Colbert, a frequent critic of former President Donald Trump, had used his show to address topics tied to the network’s parent company, Paramount Global, and its legal and business entanglements. In the weeks before CBS announced the cancellation, Colbert joked about Paramount settling a lawsuit with Trump shortly before the company’s planned merger with Skydance Media, a deal that required administrative approval to proceed.
Oliver visited Colbert’s "Late Show" in the days after the cancellation to express support, and the Emmy win months later crystallized a public moment for both the comedian and the broader late-night community. The award and the surrounding commentary underscored tensions among performers, networks and viewers over programming decisions, the impact of corporate deals on editorial spaces, and the sometimes performative interplay between awards shows and industry controversies.
Colbert’s win for Outstanding Talk Series renewed attention on the circumstances of the cancellation, but CBS has maintained that the decision was driven by financial considerations. The exchange between Oliver and Kimmel on Monday offered a lighter, behind-the-scenes glimpse of how late-night peers processed the award and the uproar that followed the surprise network move.