Stephen Colbert's Best-Ever 'Late Show' Interviews Are Why We'll Miss Him So Much

By Jessica Sager Parade - Entertainment Stories

Updated May 21, 2026 6:30 AM

When The Late Show with Stephen Colbert takes its final bow on May 21, 2026, leaving behind an indelible mark on not just comedy and pop culture, but also the fight to preserve democracy.

CBS announced that the staple show would end not long after the network settled a lawsuit from President Donald Trump, and the coincidental timing wasn't lost on anyone-least of all Stephen Colbert himself, who was more diplomatic than he needed to be about it.

"I do not dispute their rationale. I do make jokes about it. But I also completely understand why people would say (A) that doesn't make sense to me and (B) that seems fishy to me, because the network did it to themselves by bending the knee to the Trump administration over a $20 billion, settled for $16 million, completely frivolous lawsuit," Colbert explained to the New York Times in April. "It's possible that two things can be true. Broadcast can be in trouble. They cannot monetize because of things like YouTube, because of the competition of streaming. They've got the books, and I do not have any desire to debate them over what they say their business model is and how it does not work for them anymore. But less than two years before they called to say it's over, they were very eager for me to be signed for a long time. So, something changed."

Hosted by The Daily Show and The Colbert Report alum since 2015, The Late Show's interviews often transcended other late night chat shows, striking strong emotional chords as much as tickling audiences' funny bones.

Colbert's sitdowns have touched on heavy topics including grief, trauma, government censorship and more. Of course, he also made us laugh a lot-and sometimes cry, sing and nerd out, too.

Here are the best Late Show with Stephen Colbert interviews, ranked.

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Stephen Colbert's Best Late Show Interviews

21. James Talarico

What made Colbert's February 2016 interview with Rep. James Talarico (D-Tx.) so remarkable is simply that it ticked off the Federal Communications Commission (FCC) and the CBS suits so much that they refused to air it. Thankfully, YouTube exists, because it was a particularly poignant conversation that couldn't have come at a more crucial time-and Colbert addressed the manufactured controversy head-on.

20. Conan O'Brien

Conan O'Brien appeared on The Late Show With Stephen Colbert on Nov. 1, 2019, where he turned the tables (er, desk) and interviewed Colbert himself-and learned that Colbert was rejected as a writer for O'Brien's show!

19. Tiffany Haddish

Colbert clearly had a (very innocent and adorable) crush! He couldn't stop giggling and beaming at Girls Trip star Tiffany Haddish during her first appearance on The Late Show in August 2017.

"I think I have a Tiffany Haddish problem now," he said. "You're amazing. You're extraordinary ... What a joy, just to sit next to you."

Haddish knew what was up, telling Colbert that on her list of goals was to someday be on his show and "have you googly-eye me, like, yes."

18. Christine Baranski

Christine Baranski and Colbert had a truly delightful singalong to Steven Sondheim's "Side by Side" when the Good Fight star stopped by in 2021.

17. Dominic Monaghan, Billy Boyd and Peter Jackson

Colbert is a huge Lord of the Rings fan, and stars Dominic Monaghan and Billy Boyd joined forces with director Peter Jackson to quiz the host (and future LOTR franchise screenwriter!) about his knowledge of the J.R.R. Tolkien books and films.

16. BTS

C'mon, don't act like this wasn't, well, "Dynamite."

15. Andrew Garfield

Andrew Garfield, whose mother died just before filming his Oscar-nominated turn in Tick, Tick ... Boom!, reflected on grief when he appeared on The Late Show in 2021-and Colbert, ever the pro, knew better than to interrupt or go to a commercial during something so profound.

14. Anderson Cooper

Similarly to Garfield, Anderson Cooper had a tear-jerking chat with Colbert in October 2025 about mourning the people you love most. Colbert, who lost his father and two older brothers in a plane crash when he was a child, was visibly and deeply moved.

"Listening to others has changed my life," Cooper said of coping with grief. "It has saved my life."

13. Donald Trump

While Colbert's fellow late night host Jimmy Fallon got flak for giving Donald Trump a softball interview in 2016, Colbert took the opposite approach, grilling the then-presidential hopeful on his rhetoric and policy positions instead of his hair. It may explain why he's held such a grudge for over a decade, with Paramount effectively ending the show so Trump would approve of their merger with Warner Bros. Discovery.

12. Malala Yousafzai

Colbert chatted with Malala Yousafzai about human rights and global unrest-and added levity with card tricks.

11. Greta Thunberg

Greta Thunberg, climate and human rights activist, chatted about protecting the planet and activism. Colbert strikes a balance of admiring her youth without treating her like a child, while also reminding the world that we can tackle serious problems and still appreciate levity at the same time.

10. Barack Obama

During a December 2020 appearance on The Late Show, Obama got to answer questions he'd never been asked in an interview before, leading to some genuine revelations (including one each about Elton John and Dolly Parton) as well as some pretty hilarious moments.

9. Jon Stewart

Jon Stewart helped Colbert get his start, first on The Daily Show, then on The Colbert Report, and seeing them reunite in July 2016 amid a world full of even more extreme "truthiness" than before-and to celebrate the resignation of Roger Ailes from Fox News following allegations of sexual harassment, misconduct and assault-was magical.

8. Helen Mirren

During a 2018 visit to The Late Show, Oscar-winning Dame Helen Mirren brought Colbert to tears with a reading of the poem "Ulysses" by Alfred Lord Tennyson.

"You got me," he said, his eyes welled up.

Mirren replied, "It made me cry, too!"

7. Bernie Sanders

Colbert featured beloved mitten enthusiast Sen. Bernie Sanders (I-Vt.) and afforded him the rare opportunity to respond to critical passages in Hillary Clinton's memoir, What Happened, in which she pointed the finger at the Vermont Independent for her loss to Trump.

A quick a refresher: Sanders held 38 campaign rallies for Clinton after she won the 2016 nomination-more than Clinton herself did in her entire run-and more Sanders supporters voted for Clinton in 2016 than 2008 Clinton supporters voted forBarack Obama. Despite all of this, and the Democratic National Committee stacking the deck in her favor, she still blames him for loss, perhaps because it's easier on the ego than self-reflection would be.

Sanders became a regular guest on The Late Show, often to promote increasingly popular progressive ideals, including a higher minimum wage and Medicare for All, as well as the fight against fascism during Trump's second term.

6. Joe Biden

Then-Vice President Joe Biden appeared on The Late Show with Stephen Colbert in September 2015, where they shared laughs as well as a moving exchange about living through grief.

5. Jimmy Fallon, Jimmy Kimmel, Seth Meyers and John Oliver

Strike Force Five-Jimmy Kimmel Live!host Jimmy Kimmel, The Tonight Show host Fallon, Last Week Tonight host and fellow Daily Show alum John Oliver and Late Night host Seth Meyers' name for their WGA/SAG-AFTRA strike podcast-was in full effect for one of Colbert's final episodes of The Late Show on May 11, 2026, showing their support for and solidarity with their longtime friend and late night comrade amid his (likely) politically motivated cancellation. Further putting their money where their mouths are, each host's shows will go dark for the Late Show finale.

4. Lady Gaga

Lady Gaga appeared on The Late Show with Stephen Colbert in October 2018 to promote A Star Is Born, but her discussion about Supreme Court Justice Brett Kavanaugh was one of the most memorable moments, not just of the episode, but of Colbert's Late Show's tenure. The "Die With a Smile" singer's somber, serious and thoughtful explanation of the trauma associated with the sexual assault Dr. Christine Blasey Ford described suffering at the hands of Kavanaugh (which he denied) is a must-watch-not just in the context of Ford's allegations, but of all abuse survivors.

3. Ian McKellen

In a lengthy sitdown, Sir Ian McKellen chatted with Colbert about theater and his illustrious career-but it was his moving monologue about the plight of immigrants from Sir Thomas More. (While many attribute the piece to William Shakespeare, the writer is actually unknown.)

2. David Letterman

Colbert's predecessor, David Letterman, joined him for one of Colbert's final Late Show episodes. Letterman excoriated CBS and Paramount and called them "lying weasels" for canceling the late night staple.

"I will say-and I have every right to be pissed off, so I'll be pissed off here a little bit," Letterman fumed. "You can take a man's show, but you can't take a man's voice."

1. Keanu Reeves

Keanu Reeves appeared on The Late Show with Stephen Colbert on May 10, 2019, and gave such a moving (and "breathtaking") response to a question about death that he inspired the host to create "The Colbert Questionert". Yes, he really is perfect.

This story was originally published May 21, 2026 at 6:23 AM.