Stephen Colbert’s Best ‘Late Show’ Moments

• “That Nice Old Man Just Gave Me My Show”

  

  Just three days into Colbert’s then-rocky tenure as Late Show host, he interviewed then-Vice President Joe Biden in a moving two-part discussion about loss (Biden’s son Beau had recently died and Colbert’s father and two brothers famously died in a plane crash in 1974), grief and faith. The sit-down helped Colbert, still trying to adjust to hosting a show as himself after nine years of playing a self-proclaimed “high-class idiot” on The Colbert Report, recognize that he could have memorable conversations as himself. After the interview was over, Colbert, as he’s recalled multiple times since including to Jon Stewart in one of the latter’s many appearances on The Late Show (see below), told his executive producer Tom Purcell, “that nice old man just gave me my show.”

  “And what I meant was how you actually talked to someone as myself, because what he was sharing with me in that moment was so intimate and speaking so specifically to my own experience that the only way to receive it was really as the real me,” Colbert told NPR in 2021.

  He told CBS News’ John Dickerson in 2015, “It was one of … the most sublime moments I’ve ever had onstage, was to be there and have the ability, or to have the responsibility and the privilege to receive that from him.”

• Jon Stewart’s Many Appearances

  

  Before returning to The Daily Show, Jon Stewart, as a Late Show executive producer, would make occasional appearances on his longtime friend and Daily Show alum’s CBS show, often popping up from behind Colbert’s desk where, it was joked, Stewart was living. One memorable cameo came towards the end of the 2016 Republican National Convention, where Stewart, largely absent during the 2016 election after leaving his nightly gig hosting The Daily Show in 2015, delivered a scorching takedown of Fox News, arguing that the GOP’s chosen candidate of Donald Trump “clearly embodies all the things that they have for years said that they have hated about Barack Obama.” Stewart then aired footage of people on Fox News calling Obama inexperienced, divisive, thin-skinned and a raging narcissist. “A thin-skinned narcissist with no government experience. Yes, that sounds exactly like Barack Obama,” Stewart said as a picture of Trump popped up on the left side of the screen. Stewart later added, after airing clips of Sean Hannity criticizing Obama for divisiveness, being too elite and not Christian, “Either [Hannity] and his friends are lying about being bothered by thin-skinned, authoritarian, less-than-Christian readers-of-prompters being president or they don’t care as long as it’s their thin-skinned, prompter, authoritarian, tyrant narcissist,” Stewart summarized. He then called out those who felt they “owned” the U.S. and want their country back. “This country isn’t yours. You don’t own it,” he said. “You don’t own patriotism; you don’t own Christianity. … I see you and I see your bullshit.”

• Trying to Get Onstage at the 2016 DNC

  

  For his first presidential campaign season as host of The Late Show, the 2016 contest between Hillary Clinton and Donald Trump, Colbert transformed himself into the Hunger Games-inspired character Julius Flickerman, blue wig and all. As part of the bit, Colbert attended both the Republican and Democratic National Conventions in character. At the RNC, he was seemingly able to easily take to the stage before the event began and deliver a few lines of a speech before security removed him. “I know I’m not supposed to be up here, but let’s be honest, neither is Donald Trump,” Colbert memorably quipped.

  But at the DNC the following week, he had more difficulty reaching the podium, all of which was documented, amid his jokes about the battle between Clinton and Bernie Sanders for the nomination and how RNC attendees had chanted “lock her up,” in his pre-taped segment from the Wells Fargo Center in Philadelphia. Bearing a podium pass, Colbert is shown pleading with officials, enlisting Nancy Pelosi to help (“I’m with her,” he says at one point, to no avail) and even pacing back and forth in front of the stage (to the sounds of “The Star-Spangled Banner”) and trying to outrun security. It’s only when he tapes a promo for the affiliates that he realizes he has an unobstructed path to glory and makes a break for it, rolling onto the stage. Victory! “God bless podiums,” Colbert says as security tries to remove him from the stage. “I’m not one to gloat, but I won!” Back at his desk, the host insists “none of that was staged.” It’s a reminder of Colbert’s silliness and risk-taking in a simpler political time.

• President Obama’s Job Interview

  

  The Obamas made multiple appearances on Colbert’s Late Show, with both former President Barack Obama and former first lady Michelle Obama taking the signature Colbert Questionert. Barack Obama even joined Colbert for a multi-part sit-down interview and preview of his upcoming Obama Presidential Center just days before the end of The Late Show and participated in an extended, socially distanced interview when he released the first of his two-part presidential memoir in late 2020. But arguably one of the most memorable moments came shortly before the 2016 election when Colbert, in character as office manager Randy, conducted a mock job interview with the outgoing commander-in-chief. While Colbert said he wasn’t allowed to ask about a presidential endorsement, he did get him to weigh in on some snack options. The president picked an “extra-fiber nutrient bar” that “has traveled to more than 100 countries” over a “shriveled tangerine covered in Golden Retriever hair, filled with bile that I wouldn’t leave alone with the woman I love.”

• Russia Week

  

  During Trump’s first term, Colbert responded to the investigation into Russia’s possible interference in the 2016 election, not to mention various salacious headlines about the president’s connections to the country, by traveling to Moscow where he spent a week quizzing Russians on U.S. news and snack foods, interviewing oligarch Mikhail Prokhorov and, as he later shared, being “followed.” The week features a number of memorable moments, including Colbert identifying Hillary Clinton, as he held up her picture, by saying she “used to be the next president of the United States.” When the person he’s talking to says “God” prevented that from happening, there’s a clap of thunder.

  But the centerpiece of the week was Colbert booking the presidential suite at the Ritz-Carlton where Trump, according to unsubstantiated claims in a dossier compiled by former British intelligence agent Christopher Steele, publicized by Buzzfeed in 2017, allegedly watched prostitutes urinate on the bed. The moment was also said to have been recorded, leading Colbert to refer to it as “the pee pee tape.” After asking random people in Russia for the tape proved fruitless, he checked into the hotel to see the site of the action for himself.

  “It’s soaked in history, it just washes over you. It’s not even like it’s in the past, you’re in history,” he joked. “You know when you’ve imagined something for so long and then when you see it, it just doesn’t match what you’ve pictured in your head? That’s not this feeling at all. This is right on the money.” He even jumped on the bed chanting “pee pee tape.”

  After noticing the Kremlin is clearly visible from the window across from the bed and checking the room for listening devices, breaking a piece of pottery, he pulled out a black light to check the sheets and found “fake news never happened sad” on the wall. 

• Giving Hillary Clinton Her Victory Jokes

  

  Stephen Colbert hosted a grim, live election night special on Showtime in 2016, one that proceeded in a way that even the host himself admitted he wasn’t prepared for. Still, that special isn’t on this list because it wasn’t technically an episode of The Late Show. But less than a year later, 2016 Democratic presidential candidate Hillary Clinton appeared on The Late Show to promote her book What Happened about her campaign and loss. And Colbert used the occasion to give her “a whole packet of unused Clinton victory jokes.”

  “This was a whole other script we wrote in case you won,” Colbert said, explaining that the bits included a video from Katy Perry about the “Femetariat” taking over and naked men with the words “I’m with her” on their rear ends, taking advantage of the special’s Showtime placement.

  Handing her a manila envelope, Colbert instructed, “Put that in a secure vault; no one will ever see it.”

  He added, in closing, “I wish we could have told those jokes. I wish you were our president.”

  Just weeks after the election special, Colbert explained that while they prepared for multiple outcomes, he didn’t prepare as much comedic material for the scenario that actually unfolded live on Showtime.

  “There was not a bear big enough in the world that we weren’t loaded for. We were so loaded for every possible eventuality,” Colbert said. “We had so many guests. We had so many pre-taped pieces, all based on a different eventuality. We had three shows: Hillary Clinton wins and we know; Hillary Clinton wins and we don’t know, because it’s not called before the show’s over; Donald Trump’s going to win and we don’t know, because everyone said he had such a narrow path to victory. That’s not wishful thinking, that’s what everyone was saying. And then there was the last show, which is the show we did, which is Donald Trump is going to win and we know he’s going to win. My execs and my writers were like, ‘You don’t want to write something for that?’ and I’m like, ‘No! There is nothing you can write. You don’t understand. I have 400 people in my theater. If we know Donald Trump is going to win, it’s going to be like doing stand-up comedy for one of those Chilean soccer stadiums where the villagers watch you execute one of the natives. There will be no laughter!’ We only did about 20 minutes of material before we went, ‘Fuck it, it’s going to be him, let’s just talk for another hour.’ So I think we have two and a half whole shows that you will never see of material that we had to kill that night.”

  As for the naked men, who he planned to bring out if Clinton won, Colbert recalled, “very early on [in] the evening, we were like, ‘You can let those guys go.’”

• Keanu Reeves’ Thoughts on Death Inspire The Colbert Questionert

  

  Stephen Colbert has asked numerous bold-faced names important questions such as “What is the best sandwich?” “Apples or oranges?” “What number am I thinking of” and “What do you think happens when we die?” as part of his Colbert Questionert series. (The host himself even took the quiz, finally revealing what number he was thinking of, in the final week of The Late Show.)

  But he may have Keanu Reeves to thank for the recurring segment. During a discussion about the apocalyptic stakes of Bill and Ted 3 in 2019, Colbert asked Reeves, “What do you think happens when we die?”

  Reeves took a deep breath and then said, “I know that the ones who love us will miss us.” Colbert took a beat and then shook Reeves’ hand.

  A few years later, on the Late Show podcast, Colbert recalled that Reeves’ answer and the fact that it went viral got him thinking about a different series of questions for the segment.

  “We kind of owe it to Keanu Reeves for taking a moment and giving a thoughtful, simple, heartfelt answer that moved people,” Colbert said on the podcast, recalling that he wondered, “Can we build something around that?”

  When Reeves himself took the Questionert in 2022, Colbert acknowledged his contribution and profound original answer, which the actor said he didn’t want to amend.

• The Bathtub Monologue During the COVID-19 Pandemic

  

  Viewers watched the late night hosts respond to the COVID-19 pandemic in real time in 2020. After a couple of weeks of jokes, in early March, the situation grew serious in the U.S. and led the shows to tape without audiences. Though initially production was shut down, with the series planning to go on hiatus, the late night staffers, like many people, soon found that they could work from home, and Colbert was among the first of the hosts to take viewers inside his house, more specifically his bathtub. Ahead of a rerun on Monday, March 16, 2020, The Late Show aired a surprise monologue from Colbert, singing the show’s theme song and popping up from a bubble bath. Though for this “very special social distancing edition of The Late Show,” Colbert joked it should be called “The Lather Show” with guest musical duo “Head and Shoulders,” he said, brandishing a shampoo bottle.

  Colbert said it was a “freaky, freaky time” and tried to assure viewers, “If you’re watching this from home right now, know that you’re doing the right thing.”

  The host continued to broadcast from South Carolina, with his family’s help, conducting virtual interviews with talent, before returning to New York to resume taping shows from a replica of his office (read: former storage closet) within the Ed Sullivan Theater, with the host still welcoming guests via video. In June 2021, he returned to the main Ed Sullivan Theater stage for shows with vaccinated audiences. And he swore he’d never go back to the storage closet

• An Angry Colbert Goes Live on Jan. 6, 2021 and Bashes Trump for Claiming Voter Fraud

  

  The COVID-19 pandemic kept Colbert in his mini studio at the Ed Sullivan Theater through the 2020 election, the announcement of Joe Biden’s victory and the Jan. 6, 2021 insurrection. On two key occasions in which then-President Trump challenged the election results, a visibly angry Colbert was quick to respond. On Nov. 5, 2020, as votes were still being counted, Trump delivered a speech in which he claimed there were fraudulent votes and that the election was rigged. “If you did not know that Joe Biden was getting close to 270 [electoral votes], Donald Trump just provided all the proof you will ever need,” Colbert said, sporting an all-black outfit that he said was him being “dressed for a funeral” because the president “tried really hard to kill something.” Though Colbert conceded that Trump’s lying about voter fraud was predictable, he said, “What I didn’t know is that it would hurt so much. I didn’t expect this to break my heart. For him to cast a dark shadow on our most sacred right from the briefing room in the White House — our house, not his — that is devastating.”

  Saying the president “should have some shred of decency,” Colbert urged Republicans who had supported him to speak up. “For evil to succeed, all that is necessary is for good men to do nothing,” he said.

  “Donald Trump is a fascist and when it comes to democracy versus fascism, I’m sorry, there are not fine people on both sides,” Colbert said, referencing Trump’s controversial comments after the 2017 Charlottesville tragedy. “So you need to choose: Donald Trump or the American people. This is the time to get off the Trump train, because he told you where the train is going and it’s not a passenger train and he’ll load you on it someday, too.”

  After the attack on the Capitol on Jan. 6, Colbert went live and furiously reacted to what had unfolded, saying he had “rarely been as upset as I am tonight.” He went on to call out Republicans like Senators Josh Hawley and Ted Cruz and Fox News for enabling Trump.

  “Have you had enough? After five years of coddling this president’s fascist rhetoric, guess whose followers want to burn down the Reichstag,” Colbert said. “Who could have seen this coming? Everyone. Even dummies like me. This is the most shocking, most tragic, least surprising thing I’ve ever seen. For years now, people have been telling you cowards that if you let this president lie and lie over again and then join him in that lie and say he’s right when you know for a fact he’s not, there will be a terrible price to pay. But you just thought you’d never have to pay it, too. I really do hope you’re enjoying those tax cuts. And those judges! Because they’re going to be busy throwing these idiots in jail.”

  On the first day of his second term in office, Trump pardoned or dismissed the charges against all of the nearly 1,600 people indicted in connection with Jan. 6.

  Senator Amy Klobuchar, who appeared as a guest on that episode, referenced Colbert’s Jan. 6 episode in a social media post about the end of The Late Show.

• David Letterman Returns to the Ed Sullivan Theater

  

  Colbert’s final Late Show episode also marked the end of the franchise launched by former host David Letterman in 1993. Letterman, who himself weighed in on the Late Show cancellation, calling it “pure cowardice” on CBS’ part, previously stopped by Colbert’s show as a guest in 2023 in his first time on The Late Show since he retired in 2015. During their conversation, they compared notes on their respective experiences hosting the CBS late night program. And Colbert recalled how he’d asked for Letterman’s advice, which led to the current host’s desk being on the other side of the stage, and made a specific request.

  “I asked if there was a place to hide … from my producers,” Colbert said. “You said, ‘Yes … it’s great because it’s close enough you can hear the producers calling for you, and they won’t know where you are.”

  “They’ve never found me,” Colbert continued. “But the secret might be they’re not looking. They might not care if I show up.”

  “My problem was I couldn’t hide from anybody, and it shortened my life” Letterman said. “I don’t know about you but I couldn’t leave the building until it was dark — and really, really dark. I’d be so embarrassed.”

  Letterman also marveled at how nice the theater, which was renovated before Colbert took over, had become.

  “Ladies and gentlemen, this is television of the future,” Letterman said. “I think it’s delightful. I was in the dressing room — and by the way, the dressing room is nicer than the nicest hotel I’ve ever stayed in in my life. I’ll be here through Christmas. … They have snacks in the dressing room — and a menu.”

  “We’ve fixed it up a bit,” Colbert said.

  Letterman, who’s recently lashed out at CBS execs, calling them “lying weasels,” for their decision to cancel The Late Show, returned a week before Colbert’s final episode aired, where the two threw some set furniture off of the roof and onto the CBS eye logo on the street below.

  During the interview segment, Letterman again complimented Colbert’s revamp of the studio, likening it to “the Bellagio.”

  “I will say, and I have every right to be pissed off, so I’ll pissed off here a little bit, because this theater, you folks wouldn’t be in this theater if it weren’t for me, and Stephen wouldn’t be here if it weren’t for me, and we rebuilt this theater, and then Stephen came in and look at this, it’s like the Bellagio,” Letterman said. “As we all understand, you can take a man’s show, you can’t take a man’s voice, so that’s the good news in this.”

• Christopher Nolan Spoofs ‘Oppenheimer,’ Talks Fan Theories and Rumors

  

  During the 2024 awards season, when Oppenheimer was an Oscar hopeful, director Christopher Nolan sat down with Colbert for a wide-ranging multi-part interview in which they not only discussed his acclaimed star-studded film about the father of the atomic bomb but they also delved into theories about some of Nolan’s other projects and rumors about the director himself. But before all of that, Colbert got Nolan to spoof his own film, having the director participate in a black-and-white cold open in which Colbert played Oppenheimer before his dramatic moment of reflection was cut short by Nolan spraying him with a hose and Colbert chasing him down in a comedic sequence.

  During the Princeton sit-down, Colbert asked Nolan about various Tenet fan theories and “what happens to the spinning top in Inception.” In response, Nolan revealed his approach to his sometimes enigmatic work. “You’re not meant to understand everything in Tenet. It’s not all comprehensible. … I have to have my idea of it for it to be a valid, productive ambiguity, but the point is it’s an ambiguity.”

  Nolan also addressed reports he doesn’t use email or have a cellphone (“I will carry a pay-as-you-go dumb phone”) and his dislike of Uggs, as Emily Blunt had suggested, explaining that it was more about the modern boots taking people out of the fictional world of the film. And he talked about his love of the Fast & Furious franchise and accepted the Late Show host’s offer to watch the films together.

  Returning to The Late Show just days before its series finale, Nolan joked that he rode the “Colbert bump” from that appearance all the way to the Oscars.

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