As Stephen Colbert signs off for the last time on May 21 from the Ed Sullivan Theater, a new question hangs in the air: what replaces late night’s shared cultural rhythm. MISRYOUM looks back at 10 defining moments from Colbert’s 11-year CBS run—moments that mi
When Stephen Colbert walks out for the final time on May 21, he won’t just leave a TV slot. He’ll leave behind an entire nightly habit—an American ritual—built on monologues, interviews, and the sense that the room could still laugh its way through the news.
Colbert’s last broadcast comes from the Ed Sullivan Theater in New York City. capping an 11-year tenure on CBS that reshaped “The Late Show” from the sharp edge of his Comedy Central “Colbert Report” persona into something broader: a warm. thoughtful host who repeatedly won in the ratings. with critics. and with award show voters.
His final week has brought tributes from the internet and airwaves alike. Still. the bigger change may be what happens after the last sign-off—especially in a fragmented media era where fewer things feel shared. Before that future fully arrives, here are 10 moments that have defined Colbert’s run as host.
10. Interview with James Talarico
On Feb. 16, 2026, Colbert had a scheduled interview with Texas Rep. James Talarico, who was on the campaign trail in the Democratic primary for the state’s senate seat. The interview never aired on broadcast.
Colbert said the network pulled it over fears of the FCC’s “equal time” rule. which requires broadcast networks and radio stations to give equal time to all candidates in an election. CBS denied Colbert’s claim, which escalated his frustration. Even without a broadcast airing. the interview found an audience online; on YouTube. it became a viral sensation with 9.5 million views—more than any other interview with a politician other than videos with the Obamas.
9. Will Ferrell. Exotic Animal Expert
In February 2016. while Colbert was still early in his CBS era and wearing rimless glasses. he delivered a razor-sharp response to Will Ferrell’s committed bit as an “exotic animal expert.” The exchange was comic on the surface and quick in its timing—until the “expert” turned out to be a kitty cat.
8. ‘The Lord of the Rings’ rap
Fans of Colbert’s on-screen life know one obsession stands out: his love for J.R.R. Tolkien’s “Lord of the Rings” books. In 2021, he leaned into that passion to celebrate the 20th anniversary of “The Fellowship of the Ring” movie.
Colbert joined Jon Batiste, Method Man, Killer Mike, and “LOTR” cast members—including Elijah Wood, Sean Astin, Orlando Bloom, Hugo Weaving, Andy Serkis, Billy Boyd, and Dominic Monaghan—for a rap built around the films and the fandom.
7. Conversations about grief
Colbert is often remembered for his monologues, but the most profound moments of his tenure sometimes came in conversations—when he engaged guests in authentic talk about grief.
Those moments included Andrew Garfield speaking about the recent death of his mother. and Colbert appearing as an interviewee on CNN to discuss it with Anderson Cooper. The most memorable conversation. though. came in 2024. when Colbert sat with Australian musician Nick Cave. whose two sons died in the previous year. The conversation is described as intimate, deep, and riveting.
6. ‘Stephen Colbert’ returns to say ‘farewell’ to Bill O’Reilly
Even as he worked to shed the “Stephen Colbert” character after moving from Comedy Central to CBS, Colbert wasn’t afraid to bring back the rimless glasses and “truthiness” for special occasions.
One of them came in 2017, when longtime Fox News host Bill O’Reilly was fired. The moment framed Colbert’s willingness to shift modes—comic and combative—when the news demanded it.
5. ‘A big fat bribe’
Some viewers still associate a particular Colbert monologue with his alleged cancellation. In July 2025, Colbert criticized CBS for settling a lawsuit with President Donald Trump over a “60 Minutes” interview.
He called the $16 million payment a “big fat bribe” and attacked his own corporate overlords in the process. The fact that news of his cancellation arrived soon after—described as coming for “financial reasons”—added fuel to the debate. Either way. the moment remains one of the clearest examples of Colbert delivering fearless jokes and opinions. regardless of who might be affected.
4. Nicki Minaj uncut
Celebrity interviews have always carried risk on late-night television, and Colbert spent time figuring out his approach. Still, none made more impact than Nicki Minaj.
On Aug. 13, 2018, the rapper sat for an over 13-minute uncut interview that left Colbert visibly unsettled. The segment included an improvised rap about, among other topics, a romantic relationship between the pair. Colbert was flustered and playful, and the chemistry was strong enough that Minaj returned in 2023.
3. An empty pandemic theater
In March 2020, as the COVID-19 pandemic struck and the world shut down—schools and businesses included—TV networks quickly adapted. One measure was removing audiences from talk shows like “Late Show” as a social distancing step.
Colbert’s first night in a nearly-empty theater became a historical artifact: a snapshot of a terrifying cultural moment marked by disinformation, gripping fear, and a reminder that even public figures who anchor the country through comedy couldn’t contain their own emotions.
2. ‘The gloves are off’
As the clock ticked down toward his last show, Colbert spoke with more freedom than ever before. In a monologue a week after he announced his cancellation, his tone was described as fast, furious, and funny.
The delivery worked like a signal—an instantaneous reminder of what the audience, and wider culture, was about to lose.
1. Election night 2016 monologue
A year into his CBS run, Colbert was still finding his rhythm. Many pundits were surprised by Donald Trump’s electoral victory in 2016, and Colbert—known for political humor—struggled through the emotional shift.
The monologue is described as somewhat off-the-cuff and emotional, capturing a moment where the older Colbert persona seemed to recede and “regular old Stephen Colbert” moved forward into something audiences came to love.
The moments line up with a single throughline: Colbert’s show rarely treated the news as background noise. Whether it was politics and the reach of rules. celebrity interviews that got uncomfortably real. or grief carried into the studio. the format kept dragging viewers toward the same uneasy question—what can a nightly comedy actually hold?.
On May 21, the curtain falls at the Ed Sullivan Theater. For years, “The Late Show” served as a shared place to land after the day. What replaces it won’t just be a new host. It will be a new test of how Americans fill the silence after the laughter stops.
Stephen Colbert The Late Show CBS Ed Sullivan Theater late night Donald Trump FCC equal time rule James Talarico Bill O’Reilly Nicki Minaj Nick Cave COVID-19 election night 2016
So what show takes his place??
I swear Colbert was on forever. Like how can they just replace a guy who basically explained the news every night. Also does Ed Sullivan Theater still even matter or is that just branding?
Wait, his last week ends an era but it says May 21? Is that already happened? I saw a clip where he was talking about the ratings and I thought they canceled the show bc of low views or something. Maybe I’m mixing it up with another late-night host.
Honestly late night feels different now, like everybody’s doing their own thing online and nobody agrees on anything, so it’s like the room doesn’t laugh together anymore. But I’m not sure why they act like he was the last shared thing… wasn’t he just doing jokes and interviewing people? Idk, I’ll miss the monologue though even if I fast forward half the time.