Stephen Colbert's Hilarious Boss's Day Jab at Paramount CEO David Ellison

Stephen Colbert didn't hold back on National Boss's Day (October 16th, 2025), sending a sarcastic "I love you" to his new boss, David Ellison, whose company recently sealed the deal on "The Late Show's" eventual cancellation.

TL;DR

• Stephen Colbert jokingly declared his "love" for new Paramount Skydance CEO David Ellison on National Boss's Day, quipping it might buy him "a couple more months" on air.
• "The Late Show with Stephen Colbert" is officially set to end in May 2026, with CBS citing "purely financial" reasons for the decision.
• However, many, including Colbert himself and fellow late-night host Jimmy Kimmel, suspect political motivations are at play, linking the cancellation to Colbert's prior criticism of a $16 million settlement with Donald Trump and the timing of the Paramount-Skydance merger.

Late-Night Legend Roasts the Hand That Feeds (or Stops Feeding) Him

Well, folks, trust Stephen Colbert to find the humor in even the toughest situations. On Thursday, October 16th, which happened to be National Boss's Day, "The Late Show" host took a moment during his monologue to celebrate his "new boss," David Ellison, the CEO of the recently merged Paramount Skydance. And let's just say, it was less a celebration and more a masterclass in passive-aggressive comedy.

Colbert kicked off his segment by joking about the awkwardness of Boss's Day chitchat before turning his attention to a special "David Ellison Appreciation Cam." With a deadpan expression, he delivered the ultimate sarcastic declaration:

"I want to take a moment to celebrate my new boss, Paramount CEO David Ellison: Mr. Ellison, I love you. That oughta buy us a couple more months."

That wink to the camera pretty much said it all. It was a thinly veiled jab at the man now at the helm of the company that announced the end of Colbert's show, and indeed, the entire "Late Show" institution on CBS, set for May 2026.

The End of an Era: What CBS Says, and What Everyone Else Thinks

The news that "The Late Show with Stephen Colbert" would be winding down came back in July. CBS's official line? "Purely financial" reasons. They lauded Colbert for his "cutting-edge comedy" and "must-watch monologue," calling the decision "agonizing." But let's be real, a lot of people, both inside and outside the industry, are raising an eyebrow at that explanation.

Colbert's show has consistently been a top performer in the late-night ratings game. So, what's really going on? Many speculate that the "financial reasons" might just be a convenient smokescreen for something a little more... political.

The $16 Million Question: Trump, Mergers, and "Big Fat Bribes"

Here's where things get spicy. Just a month before the cancellation announcement, in July, CBS's parent company, Paramount, settled a $16 million lawsuit with former President Donald Trump. This stemmed from a dispute over an edited 2024 interview with then-Vice President Kamala Harris on "60 Minutes."

Colbert, never one to shy away from calling out power, didn't hold back on his own network. He publicly accused CBS and Paramount of giving in to Trump to secure regulatory approval for the massive Skydance merger. He famously quipped:

"I believe this kind of complicated financial sentiment with a sitting government official has a technical name in legal circles. It’s ‘big fat bribe,’ because it all comes as Paramount’s owners are trying to get the Trump administration to approve the sale of our network to a new owner, Skydance!"

He even joked about needing $16 million himself to repair his trust in the company! The timing of the cancellation—one month after the settlement and just before the merger's final approval in August 2025—feels a little too neat for many observers.

Hollywood Whispers: Was Colbert's Cancellation Politically Motivated?

It's not just Colbert who's hinted at political motives. Fellow late-night host Jimmy Kimmel openly questioned CBS's financial claims. Network insiders also spilled the tea, telling publications that while "The Late Show" had high production costs and was "on the chopping block" for a while, staffers widely believed the axe fell for political reasons.

One staffer reportedly called it "part and parcel of the Trump shakedown settlement," while another suggested it was a "gift" from the Ellisons to Trump. Given David Ellison's new joint company, Paramount Skydance, also recently acquired "The Free Press" and named its founder, Bari Weiss, editor-in-chief of CBS News—a move that drew criticism from prominent liberals—it's easy to see why theories about political alignment are swirling.

What This Means for Stephen Colbert and Late-Night TV's Future

So, what's next for Stephen Colbert? He'll be on air through May 2026, and if this recent Boss's Day joke is any indication, we can expect more pointed (and hilarious) commentary as his tenure winds down. It's a testament to his comedic courage that he's taking direct aim at his new boss, especially when that boss oversees the very network pulling the plug on his show.

The late-night landscape is definitely shifting. With streaming changing how we consume content, and shows like Colbert's facing pressure, it's a dynamic time. Even Colbert has joked about ending up on Netflix. One thing's for sure: he's going out with a bang, not a whimper, and he's not afraid to use his platform to speak his mind, even if it means playfully jabbing the CEO in charge.

Frequently Asked Questions About The Late Show Cancellation

When exactly is "The Late Show with Stephen Colbert" ending its run?

"The Late Show with Stephen Colbert" is officially scheduled to go off the air in May 2026, marking the end of both Colbert's decade-long run as host and the entire "Late Show" franchise on CBS.

Who is David Ellison and what is Paramount Skydance?

David Ellison is the CEO of Skydance Media, which recently merged with Paramount, forming the new joint company Paramount Skydance. This merger put Ellison in a leadership position over CBS, which is Paramount's parent company.

Why was "The Late Show with Stephen Colbert" really canceled?

CBS officially stated "purely financial reasons" for the cancellation. However, strong speculation, including comments from Stephen Colbert and other industry figures like Jimmy Kimmel, suggests that the decision may have been influenced by political factors, particularly Colbert's criticism of Paramount's $16 million settlement with Donald Trump and its timing with the merger approval.

Will Stephen Colbert be moving to another network or streaming platform?

While Stephen Colbert has jokingly mentioned potentially moving to Netflix after "The Late Show" ends, there has been no official announcement regarding his future plans or whether he will host another show on a different platform.

Sources

• Based on provided articles and context.