The Defining Moments That Made ‘The Late Show With Stephen Colbert’ Television History

When Stephen Colbert took over the Ed Sullivan Theater from David Letterman in September 2015, expectations were mixed and the late-night landscape was unforgiving. The comedian struggled to find his rhythm during his first year at ‘The Late Show’, as he tried to shed his ‘Colbert Report’ persona for something better suited for a late-night talk show. What followed over the next decade was nothing short of a reinvention, not just of a format, but of a man.

As his ‘Late Show’ ends an 11-year run, canceled by CBS despite top ratings in a move some suspect was rooted in silencing a high-profile critic of President Trump, it seems Colbert may have been felled by his very willingness to stand firm. Before the curtain falls, these are the moments that cemented his place in the pantheon of late-night greatness.

Colbert’s Most Iconic Monologues and the Night He Found His Voice

Nothing transformed ‘The Late Show’ more dramatically than the 2016 presidential election. Colbert finally found his voice the night after Donald Trump’s surprise ascent to the presidency, delivering an opening monologue that was equal parts hilarious, somber, and inspirational, and he never lost it. It was the precise moment the audience at home realized this show was something genuinely different.

Colbert’s ratings took off following Trump’s first election win, with his show becoming the highest-rated late-night talk show for the 2016 to 2017 season. The political temperature of the country had found its late-night thermometer, and Colbert was holding it.

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 payment a “big fat bribe” and eviscerating his own corporate overlords. For many viewers, that monologue stands as his most courageous broadcast moment, a comedian willing to bite the hand that signed his checks in defense of the press.

The Late Show Emotional Interviews That Stopped the Room

Away from the political firepower, it is Colbert’s capacity for genuine human connection that defines his most enduring segments.

Then-Vice President Joe Biden appeared on the third episode, barely two months after the death of his son Beau Biden from cancer, and Colbert gently asked him to tell a story about Beau, sharing his own debilitating grief at the loss of his father and two older brothers in a plane crash when Colbert was just ten years old. Television rarely offers that kind of unscripted emotional honesty, and audiences have never forgotten it.

When Nick Cave visited ‘The Late Show’ in 2024 with an album about to release and the death of two of his sons forming the background, the resulting conversation had a late-night intimacy that was not in any sense entertainment in the traditional meaning. Colbert was at his most authentic throughout, not pushing for laughs, but asking real questions and mostly staying out of the way as Cave explored hopefulness and the joy that lives on the far side of grief.

When Andrew Garfield appeared on ‘The Late Show’ to promote the Netflix musical ‘Tick, Tick… Boom!’, the conversation took an emotional turn as Colbert asked Garfield about the recent passing of his mother, and the actor gave a moving description of grief as “unexpressed love” that quickly activated tear ducts across the studio. These interviews collectively built ‘The Late Show’ into a space where vulnerability was not weakness, but the whole point.

Stephen Colbert’s Political Commentary and the Moments That Made Headlines

Beyond the grief conversations, Colbert’s sharpest weapon was always political satire. Although he left his ‘Colbert Report’ persona behind for ‘The Late Show’, he reprised the character one last time to comment on the firing of longtime Fox News host Bill O’Reilly, who had in fact appeared as a guest on the program. The bit worked precisely because it felt earned, a throwback that carried years of accumulated meaning.

Colbert channeled his inner POTUS in a monologue directed at Donald Trump after Trump attacked journalist John Dickerson, and when controversy followed, Colbert responded in a subsequent episode saying “I don’t regret that. I believe he can take care of himself. I have jokes; he has the launch codes.” That particular line became one of the most quoted of his entire tenure.

On one of Season 1’s final episodes, civil rights leader Rep. John Lewis visited ‘The Late Show’ to discuss gun control regulation in the wake of the Pulse nightclub shooting in Orlando, and the segment ended with Lewis and Colbert walking over to the studio audience, where Lewis crowd-surfed through the theater. It remains one of the most joyful and symbolically resonant moments the show ever produced.

The Unforgettable Celebrity Encounters That Showed His Range

For all his reputation as a political commentator, Colbert proved repeatedly that he could hold his own in pure entertainment territory. On August 13, 2018, Nicki Minaj delivered an over-13-minute uncut interview that showed the rapper thoroughly unsettling Colbert, including an improvised rap about a romantic relationship between the pair, leaving Colbert flustered, adorable, and game enough to have her back in 2023.

Helen Mirren left Colbert speechless in March 2016 when she gave him a hello kiss on the lips, and almost exactly two years later the Oscar winner left him in tears when she recited part of Alfred Lord Tennyson’s poem “Ulysses,” with Colbert listening with his head bowed before telling her “You got me.” That exchange captured the full tonal spectrum ‘The Late Show’ could occupy in any given week.

Gordon Ramsay reviewed Colbert’s peanut butter and jelly sandwich during a memorable 2017 segment, and he was not gentle. It sounds trivial next to political monologues and grief interviews, yet moments like that reminded audiences why they tuned in every night, because anything could happen at that desk.

The Legacy of a Late-Night Era Now Closing

The final chapter of ‘The Late Show’ arrived with a bittersweet flourish. In 2025, ‘The Late Show With Stephen Colbert’ earned its first Emmy Award for Outstanding Variety Talk Series, and at the time of its cancellation it remained the most-watched late-night show, averaging 2.7 million viewers according to Nielsen ratings data.

Accepting the Emmy to rapturous applause and cheers from the audience inside Los Angeles’ Peacock Theater, Colbert reflected on ‘The Late Show’ legacy, saying he originally set out to do a late-night comedy series about “love” and then realized it was actually about “loss,” adding that he had never loved his country more desperately.

Colbert’s final weeks doubled as a victory lap, welcoming Oprah Winfrey, former President Barack Obama, and David Letterman, and reuniting with Jon Stewart, who used his appearance to rib CBS pointedly over its decision.

“One of his lasting impacts was his ability to be an absolute brilliant master of both satire and sincerity,” comedian Hasan Minhaj noted in tribute. Eleven years, one desk, and a body of work that will be argued over, rewatched, and referenced for decades to come. Which of these moments hit you hardest, and is there a segment from Colbert’s run that you think deserves to be on this list?