They’re not just colleagues. They’re not even just best friends. Stephen Colbert and John Oliver are the rarest thing television has left: a genuine, ridiculous, bulletproof bromance that somehow keeps getting better with age.

By the end of 2025, John Oliver has appeared on The Late Show with Stephen Colbert a staggering 38 times, more than any other guest in the show’s decade-long history. That’s more than Tom Hanks. More than Meryl Streep. More than any president, pop star, or Marvel hero. And every single time, the internet collectively loses its mind.

It all started back in the scrappy writers’ room of The Daily Show in 2005. Colbert, the straight-laced Catholic dad in a suit, and Oliver, the wide-eyed Brit who’d just crossed the Atlantic, became instant partners in crime. Colbert taught Oliver how to survive American network notes. Oliver taught Colbert how to swear in seven different British dialects without getting fined by the FCC.

When Colbert launched The Colbert Report later that year, Oliver was one of the first writers he poached. When Oliver was handed Last Week Tonight in 2014, Colbert’s only text was: “Don’t fuck it up, you magnificent bastard.” (Oliver still has that message saved as his phone’s lock-screen.)

On air, their chemistry is pure magic:

2015: Oliver sprints onto the Late Show stage mid-introduction, tackles Colbert in a bear hug, and screams “I MISSED YOU, YOU GLORIOUS SON OF A BITCH!” while the audience loses its collective mind.
2018: Colbert “kidnaps” Oliver from HBO, drags him onstage in fake chains, and declares Thursday nights officially “John Oliver Night forever.”
2024’s legendary cold open: Oliver walks out dressed exactly like Colbert (same suit, same tie, same hair), sits in the host chair, and starts the monologue as if he owns the place. Colbert storms in four minutes later pretending to be furious. The clip has 42 million views and counting.

But it’s the off-camera moments that turned them into a cultural phenomenon in 2025.

March: When Colbert’s son Billy needed a third open-heart surgery, Oliver cancelled an entire week of Last Week Tonight tapings and flew to Los Angeles to sit with the family for five days straight. A photo of Oliver pushing Billy in a hospital wheelchair (posted by Colbert’s wife Evie) melted the internet.
August: Colbert secretly flew to London and crashed Oliver’s sold-out Last Week Tonight live show at Royal Albert Hall. Oliver cried (actual tears) when Colbert walked out unannounced.
November: They co-produced and co-starred in the crossover special The Big Orange Secret, the first time two competing network late-night shows ever joined forces for one broadcast. 18 million people watched live across CBS and HBO Max, a record that still stands.

Critics now call them “the Avengers of late-night television.” The New York Times wrote: “Colbert and Oliver aren’t just colleagues; they’re brothers. And when these two brothers share a stage, no politician on Earth is safe.”

The most human moment came at the end of the November special. After an hour of savage Trump satire, the jokes stopped. No music. No cue cards. Just the two of them on the couch.

Oliver looked at Colbert and said, quietly:

“Fifteen years ago we were two idiots writing dick jokes in a basement.”

Colbert, eyes visibly wet, replied:

“Yeah… and I still can’t write a dick joke as good as yours.”

They laughed, hugged (a real, long, tight hug), and the camera just let it breathe.

America said “awww” in unison.

In an era when everything on TV feels manufactured, the friendship between Stephen Colbert and John Oliver is one of the last things that still feels 100% real.

They’re not just two comedians. They’re living proof that in the fake-as-hell world of television, some relationships are still beautiful, honest, and so funny they make an entire country smile (and occasionally cry).

That’s why John Oliver will always be the most frequent guest on The Late Show… Because when they’re together, television doesn’t just feel fun.

It feels like home.