Top 20 Most Iconic Moments from Late Show with Stephen Colbert

#20: Friendly Competition (2015)

David Letterman launched his CBS talk show in 1993 partly to get back at NBC’s “The Tonight Show” for picking Jay Leno as Johnny Carson’s successor. Letterman's own successor kicked off his tenure with a different attitude. During a tour of the Ed Sullivan Theater, an unexpected guest appeared on a monitor to wish Stephen Colbert luck as the new host of “The Late Show.” Colbert in turn wished Jimmy Fallon luck as the new host of “The Tonight Show.” This shocking promotion for NBC affirmed that Colbert cares more about uplifting entertainment than network politics. A little over 10 years later, Fallon formally visited the Ed Sullivan Studio to bid his old foe and friend farewell.

#19: Our Cartoon Candidate (2016)

For better or worse, Trump dumping has been a hallmark of “The Late Show” since before Donald Trump first became President of the United States. The campaign was heating up in March of 2016 when Colbert analyzed a montage of bombastic public statements. Unable to get the candidate to sit down and address this, Colbert instead interviewed “Cartoon Trump.” The animation and writer Brian Stack’s voice acting were so hysterically absurd that the character became a running gag on “The Late Show.” Finally, Colbert co-created the satirical sitcom “Our Cartoon President,” which ran on Showtime from 2018 to 2020. Though controversial, the Cartoon Trump character made an undeniable pop culture impact and some big laughs.

#18: Kristen Stewart on the Cover of the Rolling Stone (2024)

Colbert has had the honor of regularly debuting People magazine’s annual photoshoot for Sexiest Man Alive. So why should he devalue Kristen Stewart’s honor of gracing the cover of Rolling Stone magazine? That’s just what he asked the actress when he unveiled both the stunning image and CBS’s recommendation that he avoid the subject due to social media controversy. Stewart pointed out the hypocrisy in her facing backlash for showing imposing sex appeal, while men face no such scrutiny for going even steamier. Colbert agreed with this levelheaded observation, as well as Stewart’s much more crass punctuation for her critics. They were soon eclipsed by the public praise for this empowering moment.

#17: “The Lord of the Rings” Trivia (2021)

Colbert loves to talk about how Peter Jackson’s adaptation of J. R. R. Tolkien’s “The Lord of the Rings” is his favorite film franchise. But is it all just talk? When actors Billy Boyd and Dominic Monaghan appeared on “The Late Show” to commemorate the trilogy’s 20th anniversary, they hit the host with esoteric trivia questions. Unfortunately, they stumped him on the exact location of the Entmoot in Fangorn Forest. Colbert then found redemption by besting Boyd and Monaghan at a question about their own characters, sent in by Jackson himself. As the victor was gleefully awarded a pair of Monaghan’s prosthetic Hobbit ears, the fanboy inside the suave comic came out in the most lovable way.

#16: “The Lather Show” (2020)

In March 2020, most Americans’ daily lives were disrupted by the COVID-19 pandemic. But “The Late Show” was both responsibly and charmingly defiant. After the U.S. declared social distancing orders, a rerun episode was edited to feature a new monologue that Colbert taped at his home. No less surprising was that he was wearing his signature suit while chilling in a bubble bath. Behind this hilariously absurd visual was the same cutting commentary on a world ever in motion. What might have been another dated monologue became a viral time capsule. “The Lather Show with Scrubbin’ Colbath” set the standard for respecting the importance of social distancing in 2020, while assuring fans that they can still relax.

#15: “Hey Stephen” (2021)

Taylor Swift fans have wondered about the inspiration for “Hey Stephen” since 2008. Stephen Colbert seemed pretty confident about the answer back when he hosted “The Colbert Report.” As the discussion was revived by the “Taylor's Version” re-release of the album “Fearless,” the pop star made a surprise appearance on “The Late Show” to address the theory. Swift’s Colbert knowledge was indeed impressive, but she claimed to be singing about the King of Horror. Of course, she was joking. Stephen Barker Liles of Love and Theft is the most likely crush behind “Hey Stephen.” Swift at least confirming who it's not about was still a more delightful surprise to fans than it was to Colbert.

#14: Dolly Parton Moves Colbert to Tears (2020)

Colbert breaking down as Helen Mirren read Tennyson’s “Ulysses” is remembered for showing off the charismatic host’s sentimental side. Never mind when Dolly Parton shared classic poetry from the Smoky Mountains. During a virtual interview, the country icon discussed how her storytelling was inspired by her mother singing traditional folk songs like “Bury Me Beneath the Willow.” She then broke out into a soft, a cappella performance of the melancholy ballad that overwhelmed Colbert with emotion. While he laughed it off as an unexpected product of COVID-19 era stress, he also asserted that “sometimes, there's nothing happier than a cry.” This disarmingly poignant moment reminded a sensitive world of the importance in emotional catharsis, as well as in valuing traditional art.

#13: Unscripted Election Monologue (2020)

Stephen Colbert closed his 2016 presidential election coverage for Showtime with a speech calling for unity, not “politicking all the time.” He then spent the next four years basically politicking all the time. Even Joe Biden’s election in 2020 was soured for the supporter by President Trump’s refusal to concede. Votes were still being counted when Colbert opened “The Late Show” by delaying his monologue for a somber plea with Republicans to denounce Trump’s fascistic actions. However one felt about Biden’s eventual victory, Colbert’s disruptive defense of the sanctity of the democratic process was undoubtedly meaningful. Though he was very upset about Trump’s re-election in 2024, he seemed to accept that it was part of that process.

#12: “Side by Side by Side” (2021)

Colbert and stage icon Christine Baranski found that one of the many challenges in virtual interviews is performing a musical duet. Thus, it would be the perfect way to celebrate “The Late Show’s” first episode in the studio since social distancing ordinances during the COVID-19 pandemic. Colbert ended his interview with Baranski by joining her in serenading the Ed Sullivan Theater with “Side by Side by Side,” from the musical “Company.” Baranski observed that this was the first performance of Stephen Sondheim on New York’s Broadway since it went dark. They finished to a roar from the studio audience they deeply missed. And it echoed across a nation moved by this joyous expression of reunion among friends.

#11: Bill Hader’s Impressions (2019)

Naturally, one of “The Late Show’s” most viral celebrity interviews involved multiple celebrities in one. When Bill Hader appeared to promote the second season of the acclaimed HBO dramedy “Barry,” the conversation turned to his time on “Saturday Night Live.” His casual transition into celebrity impressions was so charming that Colbert joined in. The whole studio was in stitches by the time the host and the guest exchanged the distinctive mannerisms of actor James Mason. The bit wound up being an unexpected hit online. Now it’s seen as a quintessential testament to Colbert’s chemistry with his guests and Hader’s capacity to pull people into his comedic acting method. Never mind the dramatic method found on “Barry.”

#10: Kendrick Lamar’s Medley (2015)

By the second episode of his tenure on “The Late Show,” Stephen Colbert had the commentary and interview chops for a must-see talk show. It was Kendrick Lamar who turned it into must-see entertainment. His medley of four tracks from 2015’s “To Pimp a Butterfly” was backed by a band and light show that barely kept up with the skilled rapper’s powerful stage presence. Like the album itself, this almost seven-minute-long performance was massively acclaimed by critics and audiences. Not only an affirmation of Lamar’s musical prowess, the medley elevated “The Late Show” to a worthy platform for the hottest performances on TV. There was 10 years worth where that came from.

#9: Accountability (2018)

It's been difficult for the public to accept the wrongdoings of beloved entertainment figures in the wake of the #MeToo movement. It was surely no small feat for Colbert to do that with CBS CEO Les Moonves amid sexual misconduct allegations in 2018. Colbert followed a jokey monologue on the matter with a serious discussion about not only holding ideological opponents accountable. He recognized Moonves as a friend and significant supporter of “The Late Show,” but also that the punishment should fit whatever crime he's guilty of. It was a courageous example of separating personal feelings for someone from reasonable scrutiny to ensure true justice. Colbert gave a cheekier monologue after Moonves was fired from CBS shortly thereafter.

#8: Keanu Reeves Gets Philosophical (2019)

A disarmingly deep hallmark of “The Late Show” goes back to Keanu Reeves teasing “Bill & Ted Face the Music” after the project was announced. His excited ravings about the premise of saving the universe with a song piqued Colbert’s interest in the actor’s philosophical perspective. He asked his guest what he believes happens when we die, and Reeves responded, [“I know that the ones who love us will miss us.”] This loaded question became part of a 15-point survey that Colbert would regularly spring on guests. When Reeves returned to “The Late Show” in 2022, it was confirmed that his poignant statement helped inspire “The Colbert Questionair.” Leave it to someone who has to contemplate the question “What is the best sandwich?”.

#7: Andrew Garfield on Grief (2021)

Before winning a Golden Globe for “Tick, Tick… Boom!”, Andrew Garfield talked with Colbert about a devastating source of inspiration in his portrayal of Jonathan Larson. The existential dread felt by this young, ill-fated musical legend was fueled by the recent death of Garfield’s mother Lynn. The actor was in fact eager to discuss this loss, as he took comfort in the idea that grief is evidence of how deeply we love someone. Colbert gave him plenty of time to weave this moving monologue about the preciousness of legacy and the healing nature of art. The result was a viral sensation that earned Garfield further praise for his courageous and important message in Lynn’s honor.

#6: “First Drafts” Returns to the Studio (2022)

Valentine’s Day 2016 kicked off a “Late Show” holiday tradition of sharing with an audience member hilarious, fictional “first drafts” for real greeting cards. When the host was housebound by the COVID-19 pandemic, the only audience member was Evelyn McGee Colbert. Stephen Colbert’s chemistry with his wife was so endearing that after he returned to the studio, she became the permanent face of “First Drafts.” The week before Valentine’s 2022 still stands out for showing that Evie is a natural in the guest seat. Never mind that Stephen is an affectionate and fun husband to banter with. Audiences have since spent many holidays laughing and swooning with the first lady of “The Late Show.”

#5: BTS-Mania (2019)

The K-pop invasion of the 2020s can be traced back to groups like BTS. Colbert may not have been the South Korean boy band’s first host on American TV, but he cleverly signaled the cultural shift. BTS’s fab rendition of “Boy with Luv” was slickly dressed, staged like a ‘60s music show, and shot in black-and-white. Colbert’s impression of Ed Sullivan rounded out this bold homage to The Beatles’ historic American TV debut in 1964. Sure enough, BTS would become one of the biggest music acts in the world, announcing a new era in global pop culture. Fifty-five years after the British Invasion exploded, the Ed Sullivan Theater witnessed history being made yet again.

#4: Bonding with Biden (2015)

“The Late Show” welcomed a very special guest for its third episode. Then-Vice President Joe Biden wound up spending much of his interview discussing grief in the wake of his son Beau’s death from cancer. He had already lost his first wife Neilia and their daughter Naomi in a car accident in 1972. This resonated with Stephen Colbert, who lost his father and two brothers in a plane crash when he was just 10 years old. It was a moving way to start this exploration of the humanity of the future President of the United States. It was also a remarkable display of the capacity for empathy that would distinguish Colbert as a late-night talk show host.

#3: “The Daily Show” Reunion (2017)

Stephen Colbert became a household name after joining Comedy Central’s “The Daily Show” as a correspondent in 1997. He celebrated 20 years since then by gathering his old colleagues for a “Late Show” skit about how he left to host “The Colbert Report.” Jon Stewart, Samantha Bee, Rob Corddry, Ed Helms and John Oliver then sat down for a group interview. The riotous reunion put into perspective how far these comedians have come since helping to popularize modern satirical news. Colbert was eager to remind fans that he would have no nightly network talk show without “The Daily Show.” If nothing else, it was great to witness banter built on two decades of professional and friendly correspondence.

#2: The Big Fat Bribe (2025)

“The Late Show” became a major political scandal itself in 2025. Paramount Global donated $16 million to Donald Trump’s presidential library to settle a lawsuit over alleged news distortion on CBS’s “60 Minutes.” Critics suspected that this was done on threat of the FCC blocking the conglomerate’s merger with Skydance Media. Considering this a violation of freedom of press, Stephen Colbert called the settlement a “big fat bribe” in a monologue. Three days later, he announced that CBS had canceled “The Late Show.” Some believe this was an act of political censorship, while others pointed to the decline in ratings and the greater talk show industry. Either way, Colbert’s risky confrontation with his parent company showed a noble dedication to free speech.

#1: Into the Late-Night Void (2026)

The series finale of “The Late Show” goes wrong in just the right way. The surprise final guest turns out to be Sir Paul McCartney, whose interview in the studio that made him an American icon in 1964 is disrupted by technical difficulties. The cause, Neil deGrasse Tyson explains, is a literal void in late-night comedy. Colbert’s fellow hosts arrive to encourage him to stand firm to the moment that black hole engulfs the studio. It’s a surreal metaphor for what this comedy institution leaves behind in an unstable world. But performances of Elvis Costello’s “Jump Up” and The Beatles’ “Hello, Goodbye,” followed by the Ed Sullivan Theatre turning into a snow globe, make a stronger statement about “The Late Show’s” lasting spirit.

What are some other Colbert classics on “The Late Show?” Be our guest in the comments below.