‘The Late Show with Stephen Colbert’ Wins Its First Sympathy Emmy
by Keegan Kelly · Cracked.comColbert’s ‘Late Show’ took home the first Emmy in its 10-year existence post-cancellation
September 08, 2025
With less than a year left until CBS removes the last remaining vestige of its once-great late-night comedy operation, the entertainment industry has banded together to send Stephen Colbert and The Late Show off with their consolation prize.
It’s finally happened — after 33 consecutive Emmy losses, The Late Show with Stephen Colbert left this past weekend’s Creative Arts Emmys a winner as Jim Hoskinson took home this year’s award for Outstanding Directing for A Variety Series. Back in July, after Paramount announced that they wouldn’t offer Colbert an extension and would end the Late Show franchise following the expiration of his current contract, TV critics, cultural commentators, comedians, fans and Jay Leno all argued over whether the move to lay off one of President Donald Trump’s most prominent critics ahead of the FCC approving the Paramount/Skydance merger deal was politically motivated. However, one aspect of the high-profile cancellation was perfectly clear and indisputable to everyone in and around the entertainment industry: The Late Show was going to absolutely rake at awards season.
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Today, on the 10-year anniversary of Colbert’s premiere as the host of The Late Show, the late-night series once made great by David Letterman is finally an Emmy-winner on his watch, and it only took the collapse of American democracy to guilt the voters into making it happen.
When Colbert and The Late Show first began their widely-publicized, middle-aged-star-studded farewell/“fuck you” tour following the news that CBS was canning the talk show in 2026, we predicted that, after a decade of clapping politely while John Oliver accepted yet another Emmy into his considerable collection, this would be the year when Colbert and his CBS late-night show would finally receive some acknowledgement from the prestigious industry awards organizations. We also predicted that, no matter how high his ratings soar nor how many statuettes he receives between now and May, none of this near-posthumous praise will change the fate of Colbert and his Late Show.
This weekend, the Primetime Emmys bring together the television industry that is, no doubt, working tirelessly on many acceptance speeches calling out President Trump’s attacks on the media and on free speech itself. There, The Late Show with Stephen Colbert will inevitably win the award for Outstanding Talk Series that has eluded it for a decade. Colbert will deliver a sober, eloquent monologue about the importance of speaking truth to power, even when it risks retribution, and the entire theater will stand up in rapturous applause as he leaves the stage. Senators Elissa Slotkin and Elizabeth Warren will repost videos of Colbert’s speech for their Twitter followers, possibly with a fundraising link attached.
It will be, in every way, the perfect microcosm for how the Liberal establishment has handled the growing threat that the federal government poses to the First Amendment.
Rather than proactively prepare for the next assault that the Trump administration will launch on its critics, the Democrats that rallied around Colbert like he’s a Civil Rights leader will mourn a past defeat with celebratory indignation. To many of those in the opposition party, Colbert’s inevitable Emmy win will be the highlight of the awards ceremony, because there’s nothing that liberals love more than losing in style.
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