Stephen Colbert’s Best & Worst Moments on ‘The Late Show’

After 32 years, thousands of episodes, a few controversies, but many more laughs, CBS’s Late Show franchise is coming to an end with the conclusion of The Late Show With Stephen Colbert next month. And that loss is no one’s gain (aside from, perhaps, Byron Allen).

Stephen Colbert’s Late Show track record has not been spotless — he had his share of growing pains and missteps, including some listed below. However, Colbert has been, by all accounts, an upstanding steward of a venerable TV institution, even amid intense upheaval in Hollywood, the United States, and the world at large.

We’re presenting our selections for his Late Show run’s biggest highlights and lowlights below, in chronological order.

Worst: Post-Super Bowl episode

Less than half a year into his Late Show run, Colbert scored the coveted post-Super Bowl time slot. But critics considered that special February 2016 episode a fumble. Time’s Daniel D’Addario said the host seemed “stiff and uncomfortable” in his sports coverage, Variety’s David Lowry said the post-game show “felt mostly like a wasted opportunity.” And GQ’s Rohan Nadkarni called the episode “shockingly boilerplate.”

Best: Colbert’s 2016 election monologue

In November 2016, Colbert aired a live presidential-election edition of The Late Show on Showtime, titling the program Stephen Colbert’s Live Election Night Democracy’s Series Finale: Who’s Going To Clean Up This Sh**? And after the results came in, Colbert turned serious and offered his thoughts, apparently off the cuff. “In the face of something that might strike you as horrible, I think laughter is the best medicine,” he told the audience. “You cannot laugh and be afraid at the same time, and the devil cannot stand mockery.”

Worst: An offensive Trump-Putin joke

For many, Colbert went beyond the pale in May 2017 when he told President Donald Trump, “The only thing your mouth is good for is being Vladimir Putin’s c*** holster.” Viewers responded with #FireColbert tweets and accusations of homophobia, and Colbert later said on air that he would do the monologue again but would “change a few words that were cruder than they needed to be,” per Politico.

Best: Helen Mirren’s Tennyson reading

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 the Alfred Lord Tennyson poem “Ulysses.” As Mirren read Tennyson’s musings on mortality, Colbert listened close with head bowed, and at the end, he told her, “You got me.”

Best: Colbert family’s #StephenAtHome involvement

During the days of Covid-19 lockdown, Colbert and his late-night contemporaries started broadcasting from home. And Colbert’s #StephenAtHome episodes got a boost from his family members — especially wife Evie, who even got production manager and cinematographer credits. “Every member of my family has been terrific,” Colbert told viewers in April 2020. “Which, statistically, means I’m the bad roommate.”

Worst: CBS’s cancellation of the franchise

In July 2025, Colbert announced on air what many viewers had already read in the press: that CBS was bringing the Late Show franchise to an end in what the network swore wasn’t a political decision. Though Colbert graciously thanked CBS for hosting him for a decade, the comedian did rue the end of the era. “I’m not being replaced,” he said. “This is all just going away. … I wish someone else was getting it.”

Best: Colbert & Jimmy Kimmel commiserate about their shows going off the air

In contrast to the Leno-Letterman years, today’s late-night rivalry seems nothing but friendly. For example, Colbert hosted both Jimmy Fallon and Jimmy Kimmel recently, and when the latter sat down for a Late Show interview in October 2026, he and Colbert shared stories about their shows being taken off the air. Colbert said that after his show’s cancellation, he got outreaches from his high school girlfriend, George R.R. Martin, and James Taylor. And Kimmel said that during his suspension, he also “got a beautiful note” from Taylor. “I’d love to compare those [notes] because … I wanna see if J.T. did a copy-paste on us,” he quipped.

Worst: CBS’s cancellation of James Talarico interview

If CBS didn’t bow to political pressure when it cancelled The Late Show, it seemed to do so when it called off Colbert’s interview with Texas State Representative James Talarico in February 2026. As Colbert told viewers, CBS felt compelled to hold the show to equal-time rules. Colbert and Talarico seem to have gotten the last laugh, though, since the controversy over the interview has only resulted in more views and web searches, as AS USA reports.

The Late Show With Stephen Colbert, Weeknights, 11:35/10:35c, CBS