John Oliver to Kimmel: ‘The Funniest Thing Would’ve Been If You Had Won’

Guesting with Jimmy Kimmel Monday night, John Oliver playfully admitted that part of him was rooting for chaos at Sunday’s Emmys.

In this year’s most-talked about Emmy moment, Stephen Colbert brought an adoring industry crowd to its feet as he accepted the award for Outstanding Talk Series for The Late Show—the show’s first-ever win in the category—just two months after CBS announced it was canceling the show after its current season.

Though The Late Show’s win came in a category that also included Jimmy Kimmel Live!, no one seemed more thrilled for Colbert than Kimmel himself, who had openly urged Emmy voters to rally behind his CBS rival.

“It was great. We were all very happy,” Oliver told Kimmel. “I know we wanted him to win. The right thing to happen was for him to win. [But] the funniest thing to happen would have been if you had won.”

Kimmel agreed, laughing: “Right.”

“Most of me wanted him to win,” Oliver continued. “A part of me, the part of me that I like more, just wanted to see your face go, ‘Oh, no. Not like this.’” (Like The Late Show up until this year, Jimmy Kimmel Live! has also never won the Emmy for Outstanding Talk Series.)

Kimmel then revealed there was a moment on Sunday night when that nightmare scenario seemed briefly possible. “One of the drivers for one of our writers was not watching the show and went on ChatGPT or something, said, Who won the talk show Emmy. And for whatever reason, it said that we won,” Kimmel explained. “And they texted it to us. I’m like, well, this is not right, obviously. And then I was like, oh, no, do they know something? And I was like, oh, [bleep], if we win, this is a disaster.”

Oliver agreed, gleefully imagining the backlash: “You would have been so [bleep]. He had his whole staff there with him. You would have been booed onto the stage. Maybe stoned. Why do you have to ruin everything? … The first ever cut away. ‘And the winner is Jimmy Kimmel.’ ‘No! [Bleep]! Why?’”

Happily for everyone except perhaps John Oliver, disaster was averted and Kimmel got to join the chorus of colleagues cheering Colbert on.

Watch John Oliver’s interview with Kimmel at the top of this post.