In September 2015, Donald Trump made a notable appearance on CBS’s “The Late Show With Stephen Colbert,” which began with an unexpected apology from the new host. At that time, Colbert was still fresh in his role, and the tension between the two showmen hinted at a significant cultural shift that was about to unfold in America. Colbert humorously acknowledged, “I said a few things about you over the years that are, uh, you know, in polite company, perhaps, are unforgivable …” This opening remark set the stage for a night that would symbolize the contrasting paths of these two iconic figures.
Just two weeks prior to Trump’s appearance, Colbert had taken sharp jabs at the then-presidential candidate. He made fun of Trump's support from White supremacists and poked fun at his distinctive hair, quipping, “What’s on top of his head is definitely his. Now it’s up to science to decide whether or not it’s hair.” The night also featured former Florida governor Jeb Bush, who was struggling in the 2016 race. Colbert jokingly remarked, “You would think that much exposure to oranges and crazy people would have prepared him for Donald Trump.” Despite the comedic tone, Trump accepted Colbert's apology with a grin, indicating a surprisingly amicable dynamic.
As the conversation shifted to serious topics like immigration and the controversial border wall, Colbert maintained a light-hearted approach, eliciting laughter from the audience. At that moment, Trump was still seen as a New York City hotelier and reality TV star rather than a serious political contender. However, just over a year after this appearance, Trump’s unexpected victory in the 2016 election would weave his narrative closer to late-night television, particularly Colbert's show.
Initially, Colbert struggled with ratings, but his fortunes changed as he began to critique President Trump more intensely in his monologues. This shift not only revitalized his show but also secured its position as the number one late-night program for nine consecutive seasons.
On a surprising note, CBS announced on Thursday that it would cancel “The Late Show,” citing financial reasons tied to a “challenging backdrop in late night” television, which has seen declining ratings and ad revenue. The network confirmed that the show would conclude its current season and officially end in May 2026. This decision came shortly after parent company Paramount settled a $16 million dispute related to Trump’s claims concerning an unfairly edited “60 Minutes” interview, a deal that Colbert criticized as “a big fat bribe.”
The immediate reaction to the cancellation ranged from shock to skepticism regarding its motives. Representative Pramila Jayapal expressed concerns about potential political motivations behind the decision, stating, “People deserve to know if this is a politically motivated attack on free speech.” The Writers Guild of America also called for an investigation into the matter, further fueling speculation about the circumstances surrounding the show's cancellation.
A senior White House official denied any influence from the Trump administration in the cancellation, describing the news as a “pleasant surprise.” Trump himself took to social media, expressing his delight, stating, “I absolutely love that Colbert got fired. His talent was even less than his ratings.” He further suggested that Jimmy Kimmel might be next, reinforcing his ongoing feud with late-night hosts.
The evolving relationship between Trump and Colbert reflects the broader decline of late-night TV. In 2015, these shows still held significant cultural relevance, notably marked by major transitions like David Letterman’s retirement and Jimmy Fallon’s ascension at NBC. Colbert’s rise was seen as a validation of Jon Stewart’s style of political humor, which leaned left and resonated with audiences seeking comedic critiques of political events.
However, as late-night hosts found their voices in politics, the dynamics shifted. The rise of streaming services offered audiences alternative entertainment options, drawing younger viewers away from traditional late-night shows. As their influence waned, Trump’s political presence grew, complicating the landscape for late-night comedy.
Initially, Colbert maintained a somewhat amicable relationship with Trump, even conducting a playful interview via an orange phone during the 2016 campaign. But as Trump’s presidency began, Colbert’s critiques became sharper, particularly after the election. On that fateful night, Colbert addressed his audience’s despair, stating, “We have to accept Donald Trump will be the 45th president of the United States.” His biting monologues gained traction, yet Trump publicly dismissed Colbert, labeling him a “no-talent guy” while simultaneously acknowledging that Colbert’s material had boosted his ratings.
As speculation about the cancellation continues, former producers and writers from Colbert's era have voiced concerns. Rob Burnett, who produced for Letterman, expressed disbelief that a top-rated show would be canceled without deeper discussions about financial challenges. He questioned whether Colbert was offered alternatives to mitigate costs before the drastic decision was made.
Merrill Markoe, who helped launch “The Late Show,” echoed similar sentiments, linking the show's fate to the broader implications of the Trump era on political comedy. She expressed hope that Colbert would find another platform, noting the show's consistent ratings and the relative affordability of talk shows as a form of entertainment.
As Colbert continues to produce episodes until May, the future remains uncertain. Fellow producer Daniel Kellison suggested that Colbert might respond with a more provocative approach. “There’s no way he’s going to be on the air for nine months,” he speculated, hinting at the potential for a bold conclusion to a significant chapter in late-night television history.
