‘The Late Show with Stephen Colbert’: Revisit 10 memorable moments

In July of last year, CBS announced that “The Late Show” would be ending after more than 30 years on air. It was an unexpected move that continues to raise questions about the motivations for the cancellation — CBS maintains it was a purely financial decision. Regardless, the show and host Stephen Colbert, who has been at the helm since 2015, are at the beginning of the end with the series slated to end Thursday.

Colbert has had a parade of boldface names appear in the final weeks, including former President Obama; Strike Force Five a.k.a. the other late-night hosts, Jimmy Fallon, Jimmy Kimmel, Seth Meyers and John Oliver; Jon Stewart; Sally Field; Julia Louis-Dreyfus; and, of course, former “Late Show” host David Letterman (while the interview is worth watching, the wanton destruction of CBS property might be the highlight).

It has been a memorable run of shows, but there were countless interviews and monologues over the years that made Colbert and “The Late Show” a must-watch. Here, our writers share their favorite moments.

Emotional conversations about grief and faith

Nick Cave, Aug. 13, 2024

Whatever gods of promotion and programming brought Colbert together with the Australian musician Nick Cave, it was indeed, in the host’s own words, “extraordinary.” Cave and his band the Bad Seeds had performed on “The Late Show” in 2017, but with an album (“Wild God”) about to release and a book of interviews (“Faith, Hope, and Carnage”), he was here this time to talk. The death of two of his sons in previous years formed the background, but Cave’s themes are hopefulness and the joy that lives at the far side of grief. He’s eloquent, and goes deep, and their talk has a late-night intimacy; it’s not in any sense entertainment. Colbert, for his part, is at his most authentic; he’s not pushing for laughs, here and there building on something Cave says, or quoting a verse of Leonard Cohen about Jesus and drowning men, asking real questions but mostly staying out of the way. He’s visibly moved at the end, announcing to the viewers at home that they’ve seen only a “scrap” of their talk, and the whole thing will be online as soon as possible. (It still is.) — Robert Lloyd

Andrew Garfield, Nov. 22, 2021

When Andrew Garfield stopped by “The Late Show” during its seventh season to promote the Netflix musical “Tick, Tick … Boom!,” he offered the usual talk show guest talking points — discussing his preparation for the role (in this case, the musicality required to play the late composer and playwright Jonathan Larson), told a funny story (about director Lin-Manuel Miranda) and engaged with the audience (by singing as they clapped along). Then things took an emotional turn as Colbert, in touching on Larson’s death, asked Garfield about his experience with grief with the recent passing of his mother and the healing nature of art in navigating it. The actor, his voice slightly shaky, gave a moving description of grief as “unexpressed love” that quickly activated tear ducts. It was a sweet, tender and beautiful reminder of a universal feeling. And it was proof that late night shows don’t always have to make you laugh — they can help you feel too. — Yvonne Villarreal

Keanu Reeves, May 10, 2019

“I know that the ones who love us will miss us.” That was Keanu Reeves’ answer to Colbert’s almost innocuous question: “What do you think happens to us when we die, Keanu Reeves?” It was as poignant and heart-wrenching as anything he said in the whole interview about “John Wick 3,” the film he was there to promote. Said at the end of the interview with nary a smirk, with thought behind it and eye contact with Colbert that seemed to connotate more than just a “here’s my answer” response, the host could only smile a knowing smile and shake Reeves’ hand as the audience reacted with an “awww” that rang through the internet with infinite memes and re-posts. — Jevon Phillips

Dua Lipa, Feb. 3, 2022

Colbert proved just how malleable he can make the late-night format during an interview with Dua Lipa. The pop star, coming off the massive success of her “Future Nostalgia” album, made an appearance to ostensibly plug her tour, lifestyle newsletter and book podcast, but viewers were treated to something more philosophical instead. The host gave her a platform to speak thoughtfully about the effects of the pandemic, her relationship to books and, at one point, allowed her to ask him whatever she liked. She asked if his comedy ever overlaps with his faith, something Colbert has been open about. “Does one ever win out?” she asked.

Colbert responded with a joke before expounding on the ideas of love and sacrifice, how they relate to fear and how comedy is used as an antidote. “If there’s some relationship between my faith and my comedy, it’s that no matter what happens you are never defeated. You must understand and see this in the light of eternity and find some way to love and laugh with each other,” he told Lipa. It’s a thoughtful conversation that could not exist on another late night program — or with any other TV personality, for that matter. — David Viramontes

Musicians and musicals

Bruce Springsteen, Oct. 25, 2021

Colbert had a warm and respectful connection with the musician, who appeared on the show several times. When the Rock and Roll Hall of Famer came on in 2021 to promote the live album and film release of “The Legendary 1979 No Nukes Concerts,” the host switched it up and grilled him with the Colbert Questionert, a series of offbeat questions that produced surprising and humorous responses. These included his favorite sandwich (“Peanut butter and jelly, 3 a.m. with a big glass of milk”), favorite action movie (“Vanishing Point”), the song he would pick if he only had one song to listen to for the rest of his life (“Summer Wind” by Frank Sinatra) and describing the rest of his life in five words (“Damn, what a f—ing ride!”). — Greg Braxton

A nod to ‘Fiddler on the Roof,’ March 1, 2016

During the show’s monologue, Colbert was riffing on Starbucks opening in Italy when a couple and their son sitting in the audience interrupted him. “When does the singing start?” asked the father. The “Kansas family” (wink wink) thought they were going to see the Broadway revival of “Fiddler on the Roof.” Colbert quipped that the beloved musical classic was playing across the street from the Ed Sullivan Theater. Guests often got in the wrong line, he said. As a consolation, Colbert offered to sing. While he stumbled over the lyrics to “Matchmaker,” “Fiddler” cast members suddenly appeared on stage, performing the song with him; they closed down the number with a rousing rendition of the show stopper “Tradition.” It was the kind of unexpected bit that viewers tuned into “The Late Show” for — it was delightful and joyful. And Colbert got to show off his musical chops. — Stacy Perman

Nicki Minaj, Aug. 13, 2018

Nicki Minaj has always been hailed as one of the best rappers of her time (male or female), and though she’s recently swerved into MAGA roadways, she visited “The Late Show” a couple of times. In probably one of the most-watched improvised rap segments ever on a late-night TV show, Minaj raps about how she would address people in public or on a song if she and Colbert were to have a relationship. Colbert was flustered, to say the least, during the interview afterward. She returned to the show in 2023 to battle rap, and again, did a bit about a possible relationship — but Colbert made sure to reference his wife, Evie, in his verse. — J.P.

Discussions about America and politics

Ocean Vuong, July 28, 2025

Authors often shine on the page but can be lackluster on camera. Then there’s poet and novelist Ocean Vuong, whose appearance on the show in 2025 was like a supernova. The MacArthur “genius grant” winner sparkled with sartorial edge as he strutted across the stage in a white tuxedo shirt to discuss his book “Emperor of Gladness.” His tiny black braid bounced and his single gold earring gleamed when Vuong delivered a hopeful soliloquy: “I’m not interested in the American dream as we know it so much as I am in Americans who dream.” Colbert often emits sarcasm, but in this moment, he let Vuong’s earnestness take the spotlight. Vuong shared a memory about watching talk shows while working at his mom’s nail salon. He delighted in seeing his immigrant mother and her co-workers, who sometimes worked 12-hour days, learn about culture and books from shows like Colbert’s. “You bring culture to working people,” he announced. And Colbert glowed, too. — Sophia Kercher

James Talarico, Feb. 16, 2026

Over the years, Colbert hosted a number of politicians and international leaders, including presidents and first ladies (Obama was the latest, in early May). But it was an up-and-coming politician who most recently made a big splash: James Talarico, the Texas Statehouse representative who is now the Democratic nominee for the U.S. Senate. However, this particular interview never made it to broadcast because Colbert said that CBS (read: its lawyers) told him the FCC’s equal time rule meant it couldn’t air. Traditionally, talk shows have been exempt from such rules, but that’s seemingly changed with the second Trump administration and the FCC led by Brendan Carr. That didn’t stop Colbert and “The Late Show” from posting it on YouTube, where the video has garnered more than 9 million views to date. The pair discussed Talarico’s grassroots campaign, the controversy involving former U.S. Rep. Colin Allred and confronting Christian nationalism. — Maira Garcia

The ‘big fat bribe’ monologue, July 14, 2025

We would be remiss in not mentioning the monologue that arguably led us to this moment. After taking some time off for vacation, Colbert returned to the show with a newly acquired mustache grown during a vacation in Turkey. The bit about the ‘stache goes on, garnering laughs from the audience, but then he begins to address current events, including Paramount’s settlement with Trump, over a “60 Minutes” interview, to the tune of $16 million, which the host calls it a “big fat bribe.” While CBS maintains that Colbert’s show was ultimately canceled for financial reasons, it has been hard not to make a connection between the timing of this joke, Trump’s feelings about the host and Skydance’s desire to get regulatory approval to acquire Paramount, the network’s parent company — which it eventually got. — M.G.