Stephen Colbert’s triumphant first-time victory for The Late Show was a major highlight of Sunday night’s Emmy Awards. But if it had been up to his fellow Daily Show alum John Oliver, things would have played out a little differently.
During an appearance on Jimmy Kimmel Live Monday night, Oliver said that “we were all very happy” for Colbert, who received a huge ovation from a Hollywood crowd that rallied around him after his show’s Trump-induced cancellation.

But then he told the host, “I will say this, we all 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,”
“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.’”
“You’re absolutely right,” Kimmel agreed, saying that if he had beaten Colbert, it would have been a “disaster.”
From the moment CBS decided to cancel The Late Show as an apparent favor to Trump ahead of parent company Paramount’s sale to David Ellison’s Skydance, the Outstanding Talk Series award was his to lose.
Even Kimmel saw the writing on the wall, putting up a For Your Consideration billboard that read, “I’m voting for Stephen.”

Colbert successfully beat both Kimmel and The Daily Show, which won in that category the previous two years. Before that, Oliver’s Last Week Tonight had a seven-year streak going before the Emmys separated his weekly show into a separate category where it competes (and is still victorious over) Saturday Night Live.
If Kimmel had won, Oliver said gleefully, “You would have been so f—ed,” adding, “You’d have been booed onto the stage.”
With that in mind, he continued, “You can see why a part of me, that as I’m saying it is now getting bigger, did kind of want that to happen.”
In his acceptance speech, which was greeted by chants of “Stephen! Stephen!” from the star-studded crowd, Colbert declared that he has “never loved my country more desperately,” urging viewers, “Stay strong, be brave, and if the elevator tries to bring you down, go crazy and punch a higher floor!”
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