Stephen Colbert’s Best ‘Late Show’ Moments
Now that CBS' long-running late night franchise has wrapped, take a look back at the memorable comedic bits, interviews and raw emotional reactions to historic events from the past decade.
Stephen Colbert’s final episode as host of The Late Show brought an end to the long-running CBS late night franchise and placed a cap on 11 years of comedic takes on current events.
While Colbert famously struggled in his first few months after taking over the series from David Letterman, he hit his stride around the time of the 2016 political conventions and later provided sharp comedic commentary on the first Trump administration with the show soaring to become the most watched show in late-night TV starting in 2017.
But Colbert didn’t delight in his success amid that political climate.
“I would trade good ratings for a better president,” Colbert told The Hollywood Reporter in 2017. “We were ready for something that galvanized people’s attention and changed their priorities. The thank-you note is to my staff for being ready — that’s the thank-you note. Because if it’s not Donald Trump, it’s something else. There will be something else that we care about, hopefully happy, possibly tragic. But we’re ready to talk about what just happened, whenever it happens now. And that’s what we’ve learned.”
He guided viewers through the early days of the COVID-19 pandemic, shifting alongside his audience to working from home, and shared raw, emotional reactions to President Trump challenging the results of the 2020 election and the Jan. 6 Capitol riot, going live at the end of the historic day in 2021.
Through it all, Colbert sat down for memorable interviews with such figures as Christopher Nolan, Keanu Reeves, Barack and Michelle Obama and then-Vice President Joe Biden in 2015 just as his Late Show was getting started.
Looking back at his Late Show legacy, Colbert recently told THR in an exit interview cover story, “I want to be remembered as a comedy show. We harvest laughter for a living, and ultimately that’s the thing I want more than anything else. I just want to make the audience laugh.”
And he’s continued to minimize his political impact from his decades in late night, first with The Daily Show, then The Colbert Report and now The Late Show.
“We’re not changing the damn world,” he said. “Have you seen the world? I promise you, if you think that I’m on some kind of agenda, then I’m really shitty at it because nothing has gone in the direction that I had hoped. I mean, nothing for 25 years.”
In honor of Colbert’s final bow, take a look back at the most memorable moments from his Late Show tenure, presented in chronological order.
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.”
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.”
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.
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.”
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.
