As "The Late Show with Stephen Colbert" comes to a close on May 21, we look back at the 10 best moments from his career on the CBS show.Show Caption
It's almost time to say goodbye to Stephen Colbert and "The Late Show" on CBS. But while he may be gone from nightly episodes on our TV screens, there are some moments from his 11-year tenure at the program that we'll never forget.The comedian and host spent his time on "Late Show" casting off his Comedy Central "Colbert Report" persona and coming into his own as warm, thoughtful and respected host who repeatedly won in the ratings, with critics and with award show voters.All of that is coming to a close on May 21, when the host signs off for the last time from the Ed Sullivan Theater in New York City.While a parade of celebrities and politicians visit his desk one last time, and the internet and airwaves are filled with tributes to the effect Colbert has had on our society and culture, it's worth reflecting back over the past decade of comedy and commentary from the man himself.We've rounded up 10 of Colbert's best moments over his career as the host of "The Late Show." Maybe after the finale, there will be another clip to add to the list.10. Interview with James TalaricoThe 10 or so months between the announcement of Colbert's cancellation and the actual finale have been a fascinating game of tug-of-war between the comedian and the higher powers at CBS. No moment exemplifies this better than in a scheduled interview with Texas Rep. James Talarico on Feb. 16, 2026, who was on the campaign trail in the Democratic primary for the state's senate seat. However, the interview never aired on broadcast.Colbert says the network pulled it fearing the FCC's "equal time" rule, requiring broadcast networks and radio stations to give equal time to all candidates in an election. CBS denies the claim (which only sent Colbert into a further rage). On YouTube, however, the thoughtful and candid interview has become a viral sensation, garnering 9.5 million views, more than any other interview with a politician other than videos with the Obamas.9. Will Ferrell, Exotic Animal ExpertOn late night, there's nothing quite like two great comedians riffing off each other, which is what we got in this interview from February 2016. So early in Colbert's tenure − he was still wearing rimless glasses − the host was pitch perfect in his response to Ferrell's committed bit as an "exotic animal expert." Spoiler alert: That is a kitty cat.8. 'The Lord of the Rings' rapAfter years playing a character on "The Daily Show" and "The Colbert Report," one of the biggest joys of Colbert's "Late Show" was meeting the man himself and all his quirks and obsessions. And as his ardent fans know, Colbert has no greater obsession than his love for J.R.R. Tolkien's "Lord of the Rings" books (which he will be pursuing more officially soon).In 2021, he got to geek out to his heart's content to celebrate the 20th anniversary of the "The Fellowship of the Ring" movie with a ridiculously fun rap alongside Jon Batiste, Method Man, Killer Mike and "LOTR" cast members Elijah Wood, Sean Astin, Orlando Bloom, Hugo Weaving, Andy Serkis, Billy Boyd and Dominic Monaghan.7. Conversations about griefColbert is remembered more for his monologues than his interviews on "Late Show," but some of the most profound moments from his tenure are when he was having honest conversations with his guests − whether they were politicians, authors, musicians, actors or his fellow comedians.The host was particularly adept at engaging his guests in authentic conversations about grief, such as when Andrew Garfield spoke about the recent death of his mother, or Colbert appeared as the interviewee on CNN to discuss it with Anderson Cooper. But the most memorable conversation occurred in 2024 in conversation with Australian musician Nick Cave, who lost his two sons in the previous year. The conversation is intimate, deep and riveting.6. 'Stephen Colbert' returns to say 'farewell' to Bill O'ReillyAlthough Colbert worked hard to shed his "Stephen Colbert" character when he moved from Comedy Central to CBS, he wasn't afraid to bring back the rimless glasses and "truthiness" for special occasions. Such an occasion occurred when longtime Fox News host Bill O'Reilly was fired in 2017.5. 'A big fat bribe'Some onlookers still think this is the monologue that got Colbert canned, and it would go down in history just for that fact. In July of 2025, Colbert criticized CBS, his own network, for settling a lawsuit with President Donald Trump over a "60 Minutes" interview, calling the $16 million payment a "big fat bribe" and eviscerating his own corporate overlords.The fact that the announcement of his cancellation came soon after, for ostensibly "financial reasons," raised eyebrows − but regardless of its effect on his contract, it remains a quintessentially Colbert moment. He was fearless in his opinions and jokes, no matter who or what they were about.4. Nicki Minaj uncutColbert is known for his political humor and grandstands, but late night has always been a celebrity- and Hollywood-focused genre of television. Colbert struggled initially to define his style of celebrity interview, but none of his couch guests ever made more of an impact than Nicki Minaj on Aug. 13, 2018.The over 13-minute uncut interview shows the rapper thoroughly unsettling Colbert, in an improvised rap about, among other things, a romantic relationship between the pair of them. Colbert was flustered and adorable, and game enough to have the rapper back in 2023.3. An empty pandemic theaterThe entire world was thrown through a loop when the COVID-19 pandemic hit in March of 2020, shutting down schools and businesses and sending the world home to stop the spread of the deadly virus. Before everyone went home for months, and before we knew all the facts about the spread of COVID, TV networks started by removing audiences from talk shows like "Late Show" as a social distancing measure.Colbert's first night in a nearly-empty theater is a historical artifact, a perfect encapsulation of a terrifying moment in our culture when disinformation was rampant, fear was gripping the world and even our most steadfast public figures, like late-night comedians, couldn't contain their own emotions. It is one of Colbert's rawest and realest moments in his career.2. 'The gloves are off'You can point to a plethora of moments over the past year in which Colbert, knowing the clock was ticking down to his last show, spoke his mind with greater freedom than ever before. In his monologue a week after he announced his cancellation, his monologue was fast, furious and funny. It was an instantaneous reminder of everything his audience (and our culture at large) was about to lose.1. Election night 2016 monologueMany pundits and talking heads were surprised by Donald Trump's electoral victory in 2016, and Colbert, known for his political humor, was chief among them. The comedian struggled to find his rhythm for the first year of his "Late Show" tenure as he shrugged off his "Stephen Colbert" persona to become just regular old Stephen Colbert. This monologue, somewhat off-the-cuff and emotional, is one of the moments where the former disappeared and the latter became beloved.
