It was late 2023. The world felt like it was breaking. Again. Hollywood was dark because of the strikes, and late-night hosts were suddenly out of a job. That is when five of the biggest names in television did something weird. They started a podcast.
Among them were two men who basically share a comedic DNA: Stephen Colbert and John Oliver.
Most people think of them as rival hosts. One is the king of the Ed Sullivan Theater; the other is the guy on HBO who spends twenty minutes explaining why the municipal water supply of a small town in Ohio is actually a nightmare. But if you look closer, their relationship is less about ratings and more about a decade-long brotherhood forged in the fires of The Daily Show.
Why Stephen Colbert with John Oliver is a rare late-night bond
The chemistry between these two isn't just "showbiz nice." It’s deeply rooted in the fact that they are both disciples of Jon Stewart. While Colbert was the breakout star of the early 2000s, Oliver was the "Senior British Correspondent" who eventually took over Stewart's chair for a summer and proved he could actually steer the ship.
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They don't compete. They collaborate.
Honestly, whenever you see Stephen Colbert with John Oliver on screen together, the vibe changes. It stops being a standard talk show interview. It becomes a "Family Meeting." That’s not just a figure of speech—it's a literal segment they do. Colbert plays the "TV Dad," and Oliver plays the chaotic "Uncle John from across the pond."
In February 2025, they did one of these meetings that went viral because of how bleakly funny it was. They sat on the couch and told the audience that if they felt powerless and overwhelmed by the world, they should. "That's the correct way to feel," they basically said. It’s that shared cynical-but-hopeful frequency that makes them a powerhouse duo.
The end of an era at The Late Show
The biggest shock to hit the comedy world recently was the announcement that The Late Show with Stephen Colbert would be ending in May 2026. This wasn't some slow fade-out. It was a bombshell. CBS cited financial pressures, but the timing felt suspicious to anyone paying attention.
John Oliver was one of the first people to speak out. He called the cancellation "terrible news for the world of comedy."
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In September 2025, for the premiere of Colbert's 11th and final season, Oliver was the first guest. It was his 21st appearance on the show. Instead of a standard "plug my new season" chat, Colbert pulled out two glasses of champagne.
"To late-night shows," Colbert toasted. "While supplies last."
Oliver, never one to miss a beat, added, "Gentlemen, it was an honor playing with you."
It felt like the end of a movie. Two titans of the genre acknowledging that the landscape of television is shifting beneath their feet. They didn't spend the whole time crying, though. Instead, they spent a massive chunk of the interview talking about The Real Housewives of Salt Lake City. Because that's what friends do—they talk about nonsense when the house is on fire.
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From Strike Force Five to the Ed Sullivan Theater
If you want to understand the depth here, you have to look at Strike Force Five. During the 2023 WGA strike, Colbert and Oliver joined forces with Jimmy Fallon, Jimmy Kimmel, and Seth Meyers. They didn't do it for fame. They did it to pay their staffs.
It was during these raw, unedited conversations that fans saw how much Oliver respects Colbert’s "professor-like" approach to comedy. Conversely, Colbert seems to delight in Oliver's ability to get genuinely angry about things like koala chlamydia or minor league baseball teams like the Erie Moon Mammoths.
There’s a specific kind of trust required to let someone else take over your desk. In 2019, they did a "flipped interview" where Oliver sat in the host's chair and grilled Colbert about date night questions. You don't do that with a rival. You do that with a peer you trust not to make you look like an idiot (or, more accurately, someone you trust to make you look like the right kind of idiot).
What people get wrong about their "rivalry"
People love to pit late-night hosts against each other. It’s a carryover from the Letterman and Leno days. But that "Late-Night War" energy doesn't exist between these two.
- They share a mentor: Both men credit Jon Stewart for their careers.
- They share a style: High-brow satire mixed with low-brow silliness.
- They share a city: Both have become quintessential New Yorkers, despite their very different origins.
Oliver once joked in a "Guest Book" segment for Colbert that he was surprised to learn the entire Late Show was made with CGI and that Colbert was actually a "tennis ball on a stick." It’s that level of comfort—being able to mock the very foundation of each other's success—that defines them.
The road to May 2026
As we approach the final months of The Late Show, expect to see more of Stephen Colbert with John Oliver. They are the last of a certain breed of "Daily Show" alumni who still hold the cultural microphone.
Oliver's Last Week Tonight is safe on HBO (well, as safe as anything is in 2026), but the loss of Colbert’s nightly platform is a massive shift. When they toasted to "while supplies last," it wasn't just a joke about Funko Pops. It was an acknowledgment that the era of the massive, network late-night institution is shrinking.
If you’re a fan of their dynamic, now is the time to pay attention. We won't get many more of these "Family Meetings."
How to keep up with the duo
If you want to see the best of their work together before the lights go out at the Ed Sullivan Theater, there are a few things you can do:
- Watch the "Family Meeting" segments on YouTube: They are the gold standard for their chemistry.
- Listen to the Strike Force Five archive: It’s the most "human" these guys have ever sounded.
- Follow the final season guest list: Oliver is almost guaranteed to make one last, possibly emotional, appearance before the May 2026 finale.
The comedy world is changing fast. Watching these two navigate it together is a reminder that even in a cutthroat industry, actual friendships can survive—and even thrive—under the spotlight. Keep an eye on the Tuesday night lineups; that's usually when the best bits happen.