The video resembles a cave painting from the Neolithic period, or perhaps something reminiscent of an era when late-night TV held significant importance: Stephen Colbert is seated at his host chair engaging in reconciliation with Donald Trump.
On the Late Show, he expresses his regret for some comments he made about you in the past, which might be considered inappropriate in a refined setting. He hopes you’ll find it in your heart to accept his apology.”
Or simpler:
“He admits that some things he said about you on the Late Show could be seen as unacceptable in polite company. He wishes for your forgiveness.
“Accepted,” Trump says, as he notes that Colbert has also said nice things.
That incident took place approximately ten years ago during the filming of The Late Show with Stephen Colbert, well before Donald Trump announced his candidacy for the 2016 presidential elections.
Last week at the Ed Sullivan Theater in New York, Colbert informed a restless audience that the show would be ending once his contract expired at the end of the following season. Since his employment on The Daily Show with Craig Kilborn back in 1997, this is not the first time Colbert has entertained us late at night. In this instance, he had no reason to apologize and may have even expected an apology; the timing suggested a distinct CBS concession to Trump.
It’s uncertain if it made a difference, but Colbert recently criticized Paramount for settling a confusing $16 million lawsuit with the president that is still pending approval for a merger with Skydance. During his monologue, Colbert playfully commented on Twitter about this situation, saying “I’m not sure if anything could restore my trust in this company, but maybe $16 million would help.” Trump responded to this on Truth Social by stating that he was glad Colbert got fired and that his talent was less than his ratings.
However, if it’s a contest between a joker and someone who isn’t amused by his jokes, Colbert might be the one with the final chuckle: He could secure an Emmy, possibly due to The Donald.
Despite several impressive stretches of excellence over its nine seasons, The Late Show With Stephen Colbert hasn’t managed to take home an Emmy award yet. (It has been nominated 31 times.) For most of this time, it went head-to-head in the top late-night category with Last Week Tonight With John Oliver, a show that Emmy voters seem to adore as much as Oliver loves his local baseball team in the minor leagues.
From 2017 to 2022, Colbert faced his former “Daily Show” colleagues as rivals in the outstanding variety talk category at annual award ceremonies, but Oliver always won. However, in 2023, it appeared that Colbert got a lucky break when Oliver’s show was moved to the outstanding variety sketch series category due to some improvised new rules intended to populate that category… but surprisingly, “The Daily Show with Trevor Noah” outperformed him instead.
In 2024, it appeared as though Colbert was on the verge of making a breakthrough with Noah no longer part of TDS. However, his former boss Jon Stewart returned for a weekly hosting role, effectively thwarting Colbert’s chances. (Colbert had previously won several Emmys during the era of The Colbert Report, prior to his stint at CBS and the Trump presidency.)
This year, it appeared we were once more on track for a “TDS” victory over “Late Show,” despite the nominee pool shrinking from five candidates to three due to fewer submissions. Despite this, Stewart has been performing exceptionally well and given “TDS” its best ratings in a decade, earning him another nomination alongside Colbert and Jimmy Kimmel. Under normal circumstances, it seemed unlikely that Emmy voters would deviate from tradition and choose Colbert. However, the Trump post – posted a month before final voting commences – has certainly shaken things up.
The significance of whether the president was directly involved in the cancellation is secondary compared to the fact that Emmys voters perceive a political conflict in the dismissal. An Emmy award may not impact immigration and Medicaid policy, but for those who dislike the leader, it’s one of the few means liberal Hollywood has to express their dissent.
Previously, they’ve made this choice, especially within this specific category, opting for Oliver, who is known for his strong political stance against Trump, over all other contenders. Notably, Oliver’s show has consistently won the top Emmy it was eligible for since Trump became the Republican nominee in 2016, a remarkable streak of nine consecutive victories out of nine attempts – an unparalleled achievement.
However, it’s possible that this could be Colbert’s year as well, particularly if Stewart acknowledges him on his own “TDS” platform, which seems likely. This is especially relevant if this is Colbert’s final opportunity for a traditional Emmy award. As for what Colbert might do next, that remains to be seen, but it’s unlikely he’ll choose mainstream TV (perhaps YouTube with some of the “TDS” team following the merger). It’s highly unlikely Colbert will retire like Johnny Carson did after his 30 years on late-night television came to an end. By the way, “The Tonight Show Starring Johnny Carson” won its first variety Emmy in its final year on air.
Interestingly, if Trump’s position leads to Colbert receiving an Emmy, it will be Trump who has facilitated Colbert’s achievement of an award that has long evaded him (The Apprentice had zero wins). Moreover, if Colbert were to win this time around for his show, he would secure a speaking platform before approximately 7 million TV viewers and countless others online. This opportunity comes at the hands of the very network that recently terminated him. It just goes to show that when you wield a powerful television microphone to deliver your punches, it’s not uncommon for those punches to be returned with equal force.
Since well before Trump, Colbert and the Republican Party have been engaged in a prolonged feud. This feud dates back to when Colbert satirized personalities like Bill O’Reilly on TDS , and then, notably, at the White Correspondents’ Dinner in 2006, where Colbert’s criticism of then-President George W. Bush caused some staff members to leave the room. In fact, Colbert has been a constant irritant for the Republican Party for a longer period than perhaps any other popular entertainer – so long that when he first started out, Newt Gingrich was the most prominent Republican figure, opposing President Bill Clinton.
It was mainly due to his sharp wit that Colbert achieved success. The White House Correspondents’ Dinner initially boosted the popularity of The Colbert Report, and later, when he began delivering political satire on The Late Show With Stephen Colbert in 2017 after moving to broadcast, his performances significantly revitalized the show, ultimately propelling him to the pinnacle of late-night television.
The trophy Trump is boasting about here is a significant one, accumulated over nearly three decades, representing numerous Republican leaders across generations.
Of course, the trophy Colbert could wind up winning may be even sweeter.
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2025-07-22 01:55