Top 10 Most Emotional Moments on The Late Show with Stephen Colbert

#10: Switching Seats with Oprah (2026)

The likes of Conan O’Brien, Amy Sedaris and Jon Stewart have sat behind the host’s desk on “The Late Show.” These “Flipped” interviews usually give Stephen Colbert a fun feel for the hot seat, but Oprah Winfrey rarely does light interviews. When the empathetic personality appeared in 2026, she guided Colbert through his feelings about his show’s impending cancellation. He admitted to being heartbroken about letting go of the friends and colleagues he's made over a decade. He and Winfrey also praised the audience as the heart of a successful talk show. As the two hosts held hands, the audience showed their appreciation, recognizing both Colbert’s immense legacy and candid vulnerability.

#9: Keanu Reeves on Death (2019)

While promoting “John Wick: Chapter 3,” Keanu Reeves confirmed “Bill & Ted Face the Music.” He was so passionate about its cosmic premise that Colbert threw his guest a philosophical curve ball. Reeves’ sincerity stunned the audience, but the actor knows about grief better than most, having lost a daughter and his partner Jennifer Syme within a 16-month span. His viral perspective inspired the “Colbert Questionert,” a 12-point survey of “Late Show” guests that includes “What do you think happens when we die?”. When Reeves returned three years later, he stood by his poignant answer.

#8: Steve Burns’s Wellness Check

Millennials were moved by Steve Burns’s video commemorating the 25th anniversary of “Blue’s Clues.” Colbert claimed to have no emotional investment in the family show beyond his own children growing up with it. Of course, he hammed up trying to keep it together while watching the original host’s touching video. Colbert gave audiences a laugh after a loss, until Burns himself made a surprise appearance. This unexpected emotional rollercoaster of a skit wound up being one of “The Late Show’s” most popular clips online. We should never forget Steve and Stephen’s lesson that there's nothing wrong about grown-ups sharing their feelings.

#7: Political Violence (2024)

On July 13, 2024, Donald Trump survived an assassination attempt while campaigning in Pennsylvania. Corey Comperatore died in the rally shooting. As fiercely as Stephen Colbert disagrees with the former and future President, he is adamant in his disdain for political violence. He opened his subsequent monologue with a solemn plea for viewers to respect one another’s humanity and that violence only results in more violence. He also expressed sorrow for what this said about the direction of the United States. This message would sadly have to be renewed following the assassination of conservative commentator and activist Charlie Kirk the following year. After all, a call for peace over irrational anger always bears repeating.

#6: Remembering John Prine (2020)

America's grief during the early days of the COVID-19 pandemic was deepened when it claimed the life of John Prine. Colbert reflected on the country-folk legend’s cultural impact and altogether decent character in a monologue filmed at home. He then presented a clip produced as an online exclusive in 2016, in which Colbert joined Prine in a performance of “That’s the Way the World Goes ‘Round.” This minimalist ballad about the ephemeral nature of life spoke volumes in this context. It affirmed that Prine left us with so much deep music to contemplate. Certainly, Colbert’s tribute to an old friend reminded us to sing along through difficult times.

#5: Colbert and Jon Batiste Discuss a Tragedy (2020)

Everyone was talking about the deaths of basketball legend Kobe Bryant and his daughter Gianna in a helicopter crash in January 2020. Colbert opened his report by naming them among the six other passengers and pilot who died in the accident. Showing respect for all of these lives was particularly important to him since he lost his father and two brothers in an aviation disaster. Colbert and bandleader Jon Batiste then discussed their personal connection with Bryant. It felt less like they were prioritizing the death of a celebrity than they were further humanizing several families’ personal tragedy. They all had difficult journeys ahead of them, but Colbert brought them more support than most public figures.

#4: A Musical (Hello,) Goodbye (2026)

“The Late Show’s” final skit starts as a mix of tragedy and hilarity, as a literal black hole in late-night comedy sucks up the entire studio. Colbert lands in a void with Elvis Costello, Jon Batiste and Louis Cato, with whom he performs Costello’s “Jump Up.” This satire of campaign fantasy and harsh reality in politics is the satirist’s final note about staying vigilant in uncertain times. Then comes the uplifting encore. Colbert, his staff, the audience and final guest Paul McCartney return to the studio to end the night with The Beatles’ "Hello, Goodbye." The black hole turning the Ed Sullivan Theatre into a snow globe may be a fantastical farewell, but the reality of Colbert’s impact is here to stay.

#3: "Love is a Victory" (2016)

The mass shooting at the Orlando nightclub Pulse on June 12, 2016, was more than a tragedy. It instilled dread in a community that continues to experience cruelty. One of Colbert’s first serious monologues could offer no answers, and lamented that these terrorist attacks have become common enough for responses to be formulaic. What he could do, however, was assert that accepting this as the way of the world is precisely what the hateful want to spread. Joy and love in defiance of despair are where true power lies. Colbert’s thoughtful, solemn tone set his statement apart from the usual script. He was sincere in the belief that only by belief in a better world could we see it.

#2: Shared Grief (2015)

Then-Vice President Joe Biden was a very special guest for the third episode of “The Late Show with Stephen Colbert.” The interview itself became very special when Colbert extended his condolences for the recent death of Biden’s son Beau to cancer. Biden had already lost his first wife Neilia and their daughter Naomi to a car accident in 1972. He himself pointed out that Colbert understood such tragedy, as his father and two brothers died in a plane crash when he was a child. It was certainly unusual for a comedic talk show to feature two people contemplating the universal experience of grief. That is, such a moment established Colbert’s unique willingness to put aside differences and gimmicks for empathy.

#1: Andrew Garfield Wants to Keep His Grief (2021)

Future Golden Globe winner Andrew Garfield turned promotion of the film “Tick, Tick… Boom!” into a historic moment in late-night. He revealed that his powerful portrayal of Jonathan Larson was influenced by the composer-playwright’s untimely death, as well as the recent passing of Lynn Garfield. Colbert then allowed the actor the opportunity to share his views on grief as a virtue. Garfield explained that it was a sign of how deeply he loves his late mother, and that art can help put such complicated feelings into perspective. His monologue soon went viral for its articulate, life-affirming philosophy. And Colbert’s encouragement of it is a lesson in how colorful personalities should know when to grant raw feeling to audiences.

What are some other “Late Night” moments that brought you to tears, and not just of laughter? Open up in the comments below.