This week marks the end of two distinctive eras of network television, as CBS’s The Late Show With Stephen Colbert will air its final episode. The show was created in 1993 by David Letterman after his controversial exit from NBC, and he held the reins for 22 years before retiring and turning the show over to Colbert, who had risen to prominence on Comedy Central as a member of The Daily Show, and then later host of his own political talkshow, The Colbert Report.

Colbert’s run on the Late Show would last 11 years. Last July, CBS shocked everyone by announcing the show’s cancellation, with the final episode to air on 21 May. Although executives claimed the decision was purely financial – even with Late Show holding the best ratings for any late-night talkshow for nine years running – many saw it as a political gesture towards Donald Trump ahead of an $8bn merger between CBS’s parent company, Paramount, and Skydance.

An ignominious end to a modern television institution to be sure, but in its way, a fitting one, considering how so many of the most memorable moments of the show over the last 11 years are tied directly to Trump. At the same time, the show’s viewers also cherished the human moments that Colbert – undoubtedly the sincerest of all late-night talkshow hosts – prioritized.

Here are the 10 greatest Late Show With Stephen Colbert moments of the last 11 years:

The Hungry for Power Games Recap, 2016

In his second year as host of Late Show, Colbert undertook an ambitious project, covering both the 2016 Republican and Democratic conventions. Accompanied by his pet ferret Caligula and donning a purple wig a la Stanley Tucci’s flamboyant television host from the Hunger Games movies, he gave us a glimpse into the even more dystopian inner workings of both parties. There are too many moments throughout The Hungry for Power Games to choose just one, but the wrap-up that aired after the conventions’ end does a good job collecting the highlights. Plus, it features an appearance from early fan favorite character Cajun Pope.

Saying Goodbye to Bill O’Reilly and ‘Stephen Colbert’, 2017

The buffoonish conservative persona that Colbert adopted on The Daily Show and The Colbert Report was heavily based on the former Fox News pundit Bill O’Reilly, the king of rightwing media cranks until accusations of sexual harassment and racism led to his network firing him. After taking some gleeful potshots at O’Reilly – with whom Colbert shared a tense on-and-off air acquaintanceship (having once stolen his toaster) – he decides to eulogize him by bringing his alter ego out of retirement for one last hurrah. An irate “Stephen Colbert” berates the American people for failing his hero, before tearfully telling “Papa Bear” to stay strong. A deserved send-off for all involved.

Alex Jones calls out Colbert in court, 2019

One of the Late Show’s best running gags revolved around the former InfoWars owner and far-right conspiracy theorist Alex Jones. In 2019, Jones was engaged in a bitter custody battle with his ex-wife and attempted to win the court’s favor by claiming his on-air antics were just an act. Colbert made a meal out of this, playing samples of Jones’s most unhinged rants and introducing his own version of him by way of Tuck Buckford, the gravel-voiced host of Brain Fight. This segment – which sees Buckford ramble about the Founding Fathers’ bowel issues, chow down on a zebra steak and rip his pants off – is particularly memorable, because it follows Jones actually namechecking Colbert in court testimony.

Sending a message to Trump, 2017

Colbert had some harsh words for Donald Trump on Day 102 of his first term in office, following the president’s interview with Face the Nation’s host and fellow CBS family member John Dickerson. Trump insulted Dickerson to his face various times (this was still something of a novelty back then), telling the respected journalist that he referred to his show as “Deface the Nation”. Colbert noted that while Dickerson was too dignified to trade insults with the president of the US, “I, sir, am no John Dickerson.” The barbs that followed were generally groan-inducing (“You’re not the Potus, you’re Bloat-us”) right up until they end, when he landed this blow: “The only thing your mouth is good for is being Vladmir Putin’s cock-holster.” The network bleeped out the curse before broadcast, but that didn’t ease the backlash, which saw #FireColbert trend across social media. Although Colbert slightly walked back his comments (mostly out of deference to those who found the joke homophobic), he didn’t apologize for it, and was eventually cleared of violating FCC standards.

Liv Tyler indulges a Lord of the Rings fantasy, 2019

Outside comedy and politics, Colbert is best known as a massive Lord of the Rings fan. Indeed, he recently announced he’ll be co-writing the next instalment of the film franchise, The Lord of the Rings: Shadow of the Past. Over the course of his Late Show run, Colbert brought up JRR Tolkien’s fantastical tales countless times and invited on numerous people involved in the film adaptations of the Lord of the Rings and Hobbit trilogies (the latter of which he appeared in a cameo role). Perhaps most memorable was his very sweet segment with Liv Tyler, who played the Elven princess Arwen in the LOTR. Knowing how much Colbert loves those movies, she brought the sword her character wielded and “indulged in a fantasy” of Colbert’s by joining with him to recreate one of her most iconic scenes.

Conan takes over, 2019

Conan O’Brien appeared on the Late Show a number of times, which was no surprise given their relationship dates back decades (when Colbert unsuccessfully applied for a writing job on Late Night with Conan O’Brien). They had previously and famously crossed over way back during the Writer’s Guild strike of 2008, when, along with Jon Stewart, they engaged in a pretend rivalry (over Mike Huckabee of all people) that resulted in a three-way fist fight on O’Brien’s show. The two carried said rivalry into 2019, when O’Brien swapped places with Colbert for a night, taking position behind the host’s desk while Colbert found himself in the hot seat. A hilarious back-and-forth ensues, giving us a glimpse of what might have been had Conan made the jump over to CBS back in the day.

Discussing grief with Joe Biden, 2020

When the Covid pandemic hit in 2020, the Late Show With Stephen Colbert became A Late Show With Stephen Colbert at Home. Filmed from inside Colbert’s actual home (with his wife, Evelyn McGee Colbert, often filling in for the studio audience), he conducted interviews via Skype. The most notable of these was his 50-minute episode with Joe Biden, then the presumptive Democratic nominee. Biden delivered a message of perseverance to Americans during this trying time, particularly those grieving loved ones lost to the virus. He and Colbert – no stranger to grief, having lost his father and brothers to a plane accident when he was only 10 years old – discussed Biden losing his own son, Beau, just a few years earlier. Biden’s show of resilience and empathy struck a chord with many a viewer, putting him in sharp contrast with Trump during this pivotal moment of the 2020 election.

Talking faith and comedy with Dua Lipa, 2022

What starts out as a by the numbers interview with pop star Dua Lipa takes a surprisingly spiritual turn when the two swap roles so that Lipa, who is prepping for a podcast, can get some interview practice. Rather than lob a softball question, Lipa asks Colbert, “Does your faith and your comedy ever overlap? And does one ever win out?” A proud Catholic, Colbert sinks his teeth into the question, discussing the way comedy helps him deal with fear and sadness, before quoting the American poet and essayist Robert Hayden: “We must not be frightened or controlled into accepting evil as our deliverance from evil. We must keep struggling to maintain our humanity, though monsters of abstraction threaten and police us.”

Strike Force Five reunite, 2026

During the battle over the Tonight Show and the subsequent late-night ratings war of the 90s, it was unthinkable that David Letterman and Jay Leno would ever appear on one another’s shows. Things have changed a lot over the years, with Colbert and four of his fellow talkshow hosts – the Tonight Show’s Jimmy Fallon, Live!’s Jimmy Kimmel, Last Week Tonight’s John Oliver and Late Night’s Seth Meyers – teaming up for the Strike Force Five podcast during the 2023 Writers Guild of America strike as a way to support their colleagues on the picket lines. The five recently reunited to lend support to Colbert ahead of his departure. They discussed their TV origins, the wrath they’ve faced from Trump, the guests they’ve made out with and the future of late-night. A testament to the respect Colbert enjoys among his peers and an inspiring show of solidarity in the face political overreach and corporate cowardice.

Colbert and Letterman destroy CBS property, 2026

Back in his Late Show era, David Letterman loved to wreak havoc by tossing CBS property off the roof of the Ed Sullivan Theater, something which Colbert was explicitly forbidden from replicating when he took over. But now, with nothing left to lose, he and Letterman enjoyed some last-minute payback, bringing back the tradition and destroying several expensive pieces of CBS-owned furniture – including Colbert’s chair. Letterman signs off by slightly misquoting the late television journalist Edward Murrow, wishing CBS “Goodnight and good luck – motherfuckers.”