As “The Late Show with Stephen Colbert” comes to an end on May 21, we look back at 10 of the best moments of his career on the CBS show.
Stephen Colbert’s final week marks the end of The Late Show
Stephen Colbert concluded, but questions remain about what will replace late night as a common cultural ritual in an age of media fragmentation.
It’s almost time to say goodbye to Stephen Colbert and CBS’s “The Late Show.” But even though he disappears from our television screens from nightly episodes, there are some moments from his 11-year tenure on the show that will never be forgotten.
The comedian and host shed his Comedy Central’s “The Colbert Report” persona and spent time on “The Late Show,” resuming his true form as a warm, thoughtful and respected host, winning over and over again in the ratings with critics and award show voters.
It all comes to an end on May 21st, when the host makes his final exit at the Ed Sullivan Theater in New York City.
As celebrities and politicians visit his desk one last time, and the internet and broadcasts are filled with tributes to Colbert’s influence on our society and culture, it’s worth taking a look back at the past decade of comedy and commentary from Colbert himself.
Here are 10 of the best moments from Colbert’s career as host of “The Late Show.” Perhaps after the finale another clip will be added to the list.
10. Interview with James Talarico
The 10 months or so between Colbert’s announcement of his cancellation and the actual final episode were a fascinating tug-of-war between Colbert and the upper management at CBS. Nowhere is this better illustrated than in an interview scheduled for February 16, 2026, with Texas Congressman James Talarico. He was campaigning in the Democratic primary for a state Senate seat. However, this interview was not broadcast on the air.
Colbert said the station went off the air in fear of the FCC’s “equal time” rule, which requires broadcast networks and radio stations to give equal time to all candidates in elections. CBS denies this claim (which only infuriated Colbert even more). But on YouTube, the thoughtful and candid interview has become a viral sensation, garnering 9.5 million views, more than any other political interview other than the Obamas’ videos.
9. Will Ferrell, exotic animal expert
There’s nothing better than two great comedians gushing over each other late at night. That’s what we got from this February 2016 interview. Early in Colbert’s tenure, when he still wore rimless glasses, the host had the perfect response to Ferrell’s dedication as an “exotic animal expert.” Spoiler alert: That’s a kitten.
8. “Lord of the Rings” rap
After years of roles on “The Daily Show” and “The Colbert Report,” one of the best parts of Colbert’s “Late Show” was getting to know Colbert himself and all his quirks and obsessions. And as his die-hard fans know, there’s nothing Colbert is more obsessed with than his love for JRR Tolkien’s Lord of the Rings books (which he plans to officially pursue in the near future).
In 2021, he joined Jon Batiste, Method Man, Killer Mike, and LOTR cast members Elijah Wood, Sean Astin, Orlando Bloom, Hugo Weaving, Andy Serkis, Billy Boyd, Dominic Monaghan, and more to get all geeky to celebrate the 20th anniversary of The Fellowship of the Ring.
7. Conversations about grief
Colbert is remembered more for his monologues than his interviews on “The Late Show,” but some of the most profound moments of his tenure were when he had honest conversations with guests, whether they were politicians, writers, musicians, actors or fellow comedians.
The hosts were especially skilled at drawing guests into genuine conversations about grief, such as when Andrew Garfield spoke about his mother’s recent death, and when Colbert appeared as an interviewee on CNN and discussed it with Anderson Cooper. But the most memorable conversation happened in 2024 with Nick Cave, an Australian musician who lost two of his sons in the previous year. The conversations are intimate, deep, and engaging.
6. “Stephen Colbert” returns to say “goodbye” to Bill O’Reilly
Colbert worked hard to shed his “Stephen Colbert” character when he moved from Comedy Central to CBS, but he wasn’t afraid to bring back his rimless glasses and “truth” for special occasions. Such happened in 2017 when longtime Fox News host Bill O’Reilly was fired.
5. “Large bribe”
Some onlookers still think this was the monologue that put Colbert in jail, and will go down in history for that fact alone. In July 2025, Colbert criticized his network, CBS, for settling a lawsuit with President Donald Trump over the “60 Minutes” interview, calling the $16 million payment “a massive bribe” and eviscerating his corporate bosses.
The fact that the cancellation was announced so soon after, ostensibly for “financial reasons,” raised some eyebrows, but regardless of the impact on the contract, it remains a classic Colbert moment. He was not afraid to share his opinions and jokes, no matter who or what they were about.
4. Nicki Minaj Uncut
Although Colbert is known for his political humor and grandstanding, late night has always been a television genre focused on celebrities and Hollywood. Colbert initially struggled to define his celebrity interview style, but none of his August 13, 2018 couch guests had a bigger influence than Nicki Minaj.
The uncut interview, which lasts more than 13 minutes, shows the rapper performing an impromptu rap about, among other things, their relationship, which thoroughly unnerves Colbert. Colbert was flustered and endearing, and there was enough charm to bring the rapper back in 2023.
3. Empty pandemic theater
When the coronavirus disease (COVID-19) pandemic struck in March 2020, the entire world was thrown for a loop, schools and businesses closed and the entire world sent home to stop the spread of the deadly virus. Months before everyone went home and before we knew all the facts about the spread of the coronavirus, television networks began removing viewers from talk shows like “The Late Show” as a social distancing measure.
Colbert’s first night in a near-empty theater was a historic achievement, a perfect encapsulation of a terrifying moment in our culture when misinformation ran rampant, fear gripped the world, and even the most staid public figures, like late-night comedians, were unable to contain their emotions. It’s one of the rawest, most real moments of Colbert’s career.
2. “The gloves are off.”
You can point to a number of moments over the past year where Colbert spoke his mind more freely than ever before, knowing that time was running out until his final show. His monologue a week after the cancellation was announced was fast-paced, intense, and funny. It was an instant reminder of everything his audience (and our culture as a whole) is losing.
1. 2016 Election Night Monologue
Many pundits and celebrities were surprised by Donald Trump’s victory in the 2016 election, but Colbert, known for his political humor, was among the top. The comedian struggled to find his rhythm during his first year on “The Late Show,” struggling to shed his “Stephen Colbert” persona and become just plain old Stephen Colbert. This monologue is somewhat outlandish and emotional, but it is one of those moments when the former disappears and the latter becomes beloved.
