Donald Trump Won't Absolutely Love That He May Have Just Handed an Emmy to Stephen Colbert

Yahoo

3 days ago

The video plays like a cave painting from the Neolithic era or, even more distantly, from when late-night television still mattered: Stephen Colbert sits in the host chair and makes amends with Donald Trump.
'I want to apologize to you because I've said a few things about you over the years that are, in polite company, perhaps unforgivable,' the Late Show host tells him. 'I hope you'll accept my apology.'
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'Accepted,' Trump says, as he notes that Colbert has also said nice things.
That moment unfolded a decade ago on the set of The Late Show With Stephen Colbert, before Trump had yet to run in a single 2016 primary.
Last week, a very different Trump-coded scene unfolded at the Ed Sullivan Theater in New York, as Colbert told a restive audience the show was being canceled after his contract expired at the end of next season. This time, Colbert, who's been regaling us on late night since he was hired on the Craig Kilborn-led Daily Show in 1997, had nothing to apologize for and, if anything, might have demanded an apology: the timing smacked of a separate CBS acquiescence to Trump.
No one can say for sure if it played a role, of course, but Colbert had just called out parent Paramount's decision to settle a head-scratching 60 Minutes lawsuit by the president for $16 million as it awaits approval for a merger with Skydance. 'I don't know if anything, anything will repair my trust in this company but, just taking a stab at it, I'd say $16 million would help,' Colbert sub-tweeted Trump in his monologue, the latest in a long line of jibes aimed at the White House occupant. Trump volleyed on Truth Social on Friday: 'I absolutely love that Colbert got fired. His talent was even less than his ratings.'
But in a battle between a jokester and a man who doesn't find him funny, Colbert may have the last laugh: He could win an Emmy thanks to The Donald.
The Late Show With Stephen Colbert has never won any Emmy in its previous nine seasons despite some notable streaks of excellence. (It has been nominated 31 times over that period.) For much of that, it competed in late-night's top category against Last Week Tonight With John Oliver, which Emmy voters love the way Oliver loves a minor-league baseball team.
Every year from 2017-22, Colbert went up against his fellow Daily Show alum as rival nominees in the outstanding variety talk category, and every year Oliver beat him. Then in 2023 Colbert seemed to catch a break when Oliver's show was shuffled off to outstanding variety sketch series under some jerry-rigged new rules designed to fill out that category … only for The Daily Show With Trevor Noah to beat him.
In 2024, Colbert finally seemed poised to break through with Noah gone from TDS — but Colbert's old boss Jon Stewart had come back for a weekly hosting spot, and so that beat him. (Colbert did win the top Emmy a couple times back in the days of The Colbert Report, pre-CBS and pre-Trump.)
This year, we seemed headed to a TDS-over-Late Show outcome once more, even with the nominee field shrunk from five just a few years ago down to three thanks to fewer submissions. Stewart has been clicking on all cylinders and given TDS its highest ratings in 10 years as he was again nominated alongside Colbert and Jimmy Kimmel. There was little reason to think Emmy voters would break with precedent and vote for Colbert. Then came the Trump post.
Whether the president actually had a hand in the cancellation matters less than the fact that Emmys voters see a partisan battle in the firing. An Emmy won't change public policy on immigration and Medicaid. But it's one of the few ways liberal Hollywood can stick it to the leader they loathe.
They have done that before, particularly in this category, choosing Oliver, the most stridently political and anti-Trump of the bunch, over all his competitors. In fact, Oliver's show has never lost the top Emmy it was eligible for since Trump first became the Republican nominee in 2016 — an astonishing run of 9-0.
But this may be Colbert's year too, especially if Stewart gives Colbert his props on his own TDS platform, as he already sharply did Monday night and could continue to in the next month ahead of final voting. (And if Colbert comedically leans into the cancellation, as he also did Monday.) That's especially true if this is Colbert's last chance for a traditional Emmy. What the comic does now is anyone's guess, but mainstream TV seems an unlikely path (more likely: YouTube with maybe some of the TDS gang post-merger). Colbert almost certainly won't retire, like another sixtysomething, Johnny Carson, did after his own 30 years on late-night came to an end. By the way, The Tonight Show Starring Johnny Carson won its first variety Emmy in its last year on the air.
In a grand irony, if Trump's stance does give Colbert the Emmy the president will have enabled the host to win an honor that has saltily eluded him. (The Apprentice went 0 for 8.) And if Colbert did finally win for this show, he would gain an acceptance-speech platform of some 7 million TV viewers, and millions more online, all on and courtesy of the the network that just canceled him. Not to mention another year on said network with nothing to lose and plenty of time to target Trump even more. That's the thing about punching someone with a TV megaphone — they can punch back.
Colbert and the GOP have actually been in a battle since long before Trump, going back to the comic's satirizing of Bill O'Reilly and other Fox News personalities on TDS and then, explosively, at the WHCD in 2006, when Colbert's skewering of then-President George W. Bush literally sent some staffers walking out of the room. In fact, Colbert has been a thorn in the side of the GOP longer than arguably any popular entertainer — so long that when he started out, the leading Republican figure was Newt Gingrich, opposing President Bill Clinton.
That jabbing has gotten Colbert where he is. The WHCD put Colbert Report on the map early in its run and then his turn to political barbs fuel-injected the sputtering Late Show With Stephen Colbert in 2017 shortly after Colbert jumped to broadcast, eventually sending the host to the top of late night.
So the trophy Trump is claiming here is a rich one, nearly 30 years in the making, on behalf of several generations of Republican leaders.
Of course, the trophy Colbert could wind up winning may be even sweeter.
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