After more than a decade behind the desk, The Late Show with Stephen Colbert is set to take its final bow on May 21, 2026, marking the end of one of late-night television’s most influential eras. When Stephen Colbert stepped into the spotlight in 2015, succeeding David Letterman, he transformed the iconic late-night institution into a cultural phenomenon of its own, and across 11 years, the show became a go-to destination for unforgettable celebrity interviews and razor-sharp political satire.

Despite remaining one of the biggest names in late-night, CBS chose to bring the show to an end, closing the curtain on The Late Show franchise. So, as the lights dim at the Ed Sullivan Theater, here are 10 unforgettable The Late Show with Stephen Colbert moments that will live on long after the final sign-off.

On February 3, 2022, Dua Lipa appeared on The Late Show with Stephen Colbert, and what began as a relaxed conversation about her music, tour, and upcoming projects soon took an unexpected turn when Colbert invited her to switch roles and try interviewing him to practice for her upcoming podcast. That is when she surprised him with a deeply reflective question: “Does your faith and comedy ever overlap, and does one ever win out?”

What followed was a complete tonal shift. Colbert opened up about his Catholic faith, grief, mortality, and the way humor helps people sit with sadness and fear instead of being overwhelmed by it, and the whole conversation resonated very strongly with viewers, gaining millions of views online, becoming one of those rare late-night moments.

On March 12, 2020, The Late Show with Stephen Colbert became one of the first major late-night shows to suspend its live studio audience as COVID-19 began reshaping television production around the world. Colbert initially broadcast from his home in South Carolina before returning to the Ed Sullivan Theater in a stripped-down, audience-free setup that completely changed the rhythm of the show.

This era reached one of its most intense and memorable points after the January 6, 2021, Capitol riot, when Colbert delivered a live monologue that carried a sharper, more emotional edge than usual. Without an audience to react or soften the moment, his anger and frustration came through unfiltered, making the segment feel even more grounded in the reality of the time.

When Liv Tyler appeared on The Late Show with Stephen Colbert while promoting her series Harlots, the interview quickly drifted into unexpected Lord of the Rings territory, thanks to Colbert’s famously deep obsession with the franchise. The real magic kicked in when Tyler revealed she had brought along Arwen’s sword from the films, knowing exactly how much it would mean to him.

From there, the segment completely blurred the line between interview and fantasy. Liv Tyler slipped back into her role as Arwen, sword raised, delivering the iconic line, “If you want him, come and claim him,” while Colbert eagerly jumped into the scene, fully living out his Middle-earth dream on national television, making it a wholesome, unforgettable moment for fans of both The Late Show and The Lord of the Rings.

Conan O’Brien appeared on The Late Show with Stephen Colbert in a special segment filmed in November 2019, where the two late-night veterans reflected on their shared history in comedy and the evolving world of television. But the interview did not stay traditional for long. O’Brien quickly moved beyond the guest seat and stepped into Colbert’s world, taking over parts of the desk and flipping the usual host–guest dynamic on its head.

What made the moment iconic was how it leaned into the larger “late-night family” energy, blending rivalry, respect, and friendship into one playful exchange. It turned into a “what if” scenario of Conan briefly hosting The Late Show himself, with both comedians feeding off sharp chemistry and quick improvisation, that uniquely stood out for fans of late-night television.

In one of Stephen Colbert’s earliest and most acclaimed interviews, then–Vice President Joe Biden appeared on The Late Show with Stephen Colbert on September 10, 2015, for a conversation that began with politics but shifted into a more personal and reflective. The talk focused on election headlines, gently moved into deeply emotional territory, as Biden spoke with striking honesty about loss, grief, and family.

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The segment became a defining early moment for Colbert’s Late Show, showing how the program could balance humor with genuine human depth. As Biden opened up about the devastating loss of his son Beau, Colbert allowed the conversation to breathe, stepping back from comedy and creating space for sincerity, resulting in a rare late-night television moment.

During The Late Show with Stephen Colbert’s special post–Super Bowl broadcast on February 7, 2016, Will Ferrell delivered one of his most chaotic and memorable appearances. Known for his over-the-top comedic style, Ferrell stormed onto the stage in full safari gear, introducing himself as a “world-class exotic animal expert” and instantly hijacking the segment. Instead of promoting Zoolander 2, he insisted the show was missing a resident animal specialist and appointed himself to the role on the spot.

As Ferrell showcased a series of wildly fabricated creatures, including a “short-spined Peruvian mongoose” that resembled a house cat and a “Mongolian bush tiger” that behaved nothing like a tiger at all, Colbert played the perfect straight man throughout, questioning Ferrell’s outrageous claims while trying to keep the segment grounded, which remains one of the show’s most iconic sketches.

While promoting her album Queen, Nicki Minaj appeared on The Late Show with Stephen Colbert, turning what was meant to be a promotional interview into an unpredictable, chaotic exchange that fans still keep coming back to. What started as a regular conversation spiraled into a more spontaneous and unfiltered moment between her and Colbert.

During the segment, Minaj leaned into her Barbie Dreams–style humor and suddenly began freestyling a playful, flirtatious rap about Colbert himself, catching him completely off guard. He became visibly flustered, laughing uncontrollably as the audience erupted around them. At one point, the moment got so unexpected and funny that Colbert literally covered his face and broke character, while Minaj kept going with effortless momentum, fully owning the chaos and turning the interview into one of those wildly memorable Late Show moments.

A recurring-style stunt from David Letterman’s CBS era (1993–2015) was brought back on The Late Show with Stephen Colbert when Letterman himself returned as a guest. What started as a nostalgic appearance quickly turned into full-blown chaos, as Letterman slipped right back into his trademark absurd, destructive comedy, treating the studio like a playground for unpolished television energy. Colbert joined in, and together they leaned into the bit, throwing and dropping CBS props and set pieces with deliberate, over-the-top abandon.

The most iconic moment is the rooftop destruction sequence itself, where the two comedians escalated the gag into a symbolic act of comedic “farewell.” It wasn’t just about breaking furniture. It carried the weight of satire, rebellion, nostalgia, and pure absurdity all at once. With the show’s end already announced, the moment felt like a final, chaotic salute to decades of late-night legacy.

Right after CBS announced the cancellation of The Late Show with Stephen Colbert, Colbert opened his monologue by addressing the end of his show. Speaking in a sharp, unfiltered tone, Colbert questioned CBS’ explanation that the cancellation was purely “financial,” saying he was not fully convinced, and made it clear that with the show coming to an end, he was no longer going to play it safe or cautious. 

He then delivered the now-iconic line, “For the next 10 months, the gloves are off,” signaling a shift into more direct, unapologetic satire. He responded bluntly with “Go f--- yourself,” delivered in his usual calm late-night cadence, which, along with the “gloves are off” declaration, quickly went viral and became one of the most discussed moments of the segment.

One of the most surprising moments came when Stephen Colbert brought together his late-night peers, Jimmy Fallon, Jimmy Kimmel, Seth Meyers, and John Oliver, the same group that originally formed the Strike Force Five podcast during the 2023 writers’ strike, on The Late Show with Stephen Colbert, during the final stretch of his run before the show’s official end.

They reunited to reflect on their shared late-night careers, joke about the chaos of the industry, and support Colbert as he prepared to leave CBS. Though often positioned as rivals in the ratings race, they appeared together like a comedic supergroup, openly acknowledging the shifting landscape of late-night television. The moment carried a strong sense of camaraderie and finality, feeling like one last encore before the stage lights dimmed on an era.

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Which moment stood out to you the most? Let us know in the comments.