John Oliver sat in his small studio, the hum of the lights above him offering a slight comfort, a reminder of how far he had come. The desk was cluttered with papers and notes, the remnants of a week spent creating another episode of Last Week Tonight, but his mind wandered far beyond the confines of his own show. It was impossible not to think about the news that had shaken the late-night world: CBS had decided to pull The Late Show with Stephen Colbert after its 2025-2026 season, its curtain call set for May 2026. It wasn’t a surprise, not really. In this industry, nothing was ever permanent. But still, the timing and the reason were hard to ignore. Colbert, the man who had become the voice of late-night, was going to be silenced—at least on CBS.

Oliver couldn’t help but smile slightly, though it was a wry, almost melancholic smile. He had known Stephen for years, both as a colleague and as a friend. The two had bonded over their shared love for comedy, political commentary, and the absurdity of the world around them. But now, Oliver could see it clearly: Colbert, freed from the constraints of his network, might finally be able to speak without fear, without restraint. The weight of a looming cancellation often pushed comedians to new limits, and Oliver couldn’t help but feel a certain excitement at the thought of what Colbert might do in his final months.

As he spoke with reporters later that Saturday, Oliver couldn’t mask his genuine disappointment, but there was a glimmer of anticipation in his eyes. “It’s terrible, terrible news for the world of comedy,” he said, his voice laced with a hint of sadness. “Stephen has been a massive influence on so many of us. He’s the heart of late-night. To see that show end—well, it’s just… it’s hard.” He paused, then added, with the faintest smirk, “But I’m partly excited to see what they’re going to do for the next ten months. I mean, without the conventional pressures of a network breathing down his neck, Colbert could do things we’ve all been waiting for him to do. The man has a lot of tricks up his sleeve.”

It was true, Oliver thought. Colbert had been playing a careful game for years. The late-night host had always been known for his sharp political satire, but there was an underlying professionalism, a degree of restraint. After all, he was always walking a fine line. But now, with his final season looming, the stakes had changed. He didn’t have to play by the same rules anymore. The thought was intoxicating. The man who had once run an entire late-night empire would soon be free to speak his mind completely.

Oliver thought about the last few weeks—the months really—since the network’s decision had come down. CBS had made its move just days after Colbert had delivered a scathing monologue, one where he criticized Paramount, CBS’s parent company. Colbert had spoken frankly about the $16 million bribe the company had paid to settle President Donald Trump’s lawsuit over a 60 Minutes interview with Vice President Kamala Harris. Colbert, with his typical biting wit, had called it exactly what it was: a bribe. And yet, this was the same network that had carried his show for years. It was impossible not to feel a touch of irony.

And that irony wasn’t lost on the public. As soon as the news broke, the internet erupted with speculation. People wondered aloud if Colbert’s firing—or rather, the decision not to renew his contract—was part of a larger political play. After all, his sharp commentary on the former president hadn’t exactly made him friends at the highest levels of corporate media. The firing came shortly after his comments, and many in the political sphere saw it as a direct response to his criticism. Democratic politicians were quick to express concern that CBS had caved to political pressure.

But Oliver wasn’t one to wallow in conspiracy theories. His show was built on calling out the absurdities of the world, not succumbing to them. And yet, even he couldn’t help but see the darker implications of the whole situation. CBS was willing to silence Colbert, the most popular late-night host in the country, because of the political pressure it was facing. The decision didn’t sit right with him.

“I love Stephen, I love his staff. I love that show,” Oliver said, his voice quiet, almost wistful. “Late-night shows mean a lot to me. Not just because I work in them, but because, growing up in England, I would watch Letterman’s show, which, of course, was Stephen’s show, and think about what a glamorous world that was.” Oliver paused, his thoughts drifting back to those early days. “It’s hard to put into words, but you don’t understand how much of an impact those shows have on you until you’re standing here doing your own. But that’s the power of late-night comedy. It’s a way to process the madness of the world, to laugh through the chaos. And now, we’re losing that.”

Still, Oliver wasn’t one to dwell in despair. As the days wore on, he found himself thinking more and more about Colbert’s future. The man would not stop. Even in the face of this enormous loss, Oliver was certain that Colbert would emerge with something even bigger. Maybe it would be a new platform, maybe something entirely different. But one thing was for sure: Colbert would find a way to make his voice heard.

Oliver knew the comedy world wasn’t going to let Colbert go down without a fight. And if Colbert’s final months on The Late Show were anything like the last few episodes he’d done, they would be a masterpiece. Without the restrictions of a network, without the looming threat of cancellation hanging over him, Colbert would finally be able to let loose.

It was a bittersweet thought. The world of late-night would lose one of its brightest stars. But at least, in the end, Colbert would be free to speak without the filters of a corporate agenda. And in the meantime, Oliver couldn’t help but anticipate the chaos that was about to unfold. Because if there was one thing that Oliver knew about Stephen Colbert, it was this: when he finally stopped caring about the rules, the world better brace itself.