Stephen Colbert bid farewell to his talk show, The Late Show with Stephen Colbert, in a memorable fashion during its penultimate episode on 20 May. In a heartwarming segment known as “Colbert Questionert,” the 62-year-old host was subjected to a series of personal questions from an array of celebrity guests, including the likes of Billy Crystal, Robert De Niro, and Mark Hamill.
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The celebrated comedian received well-wishes and questions from a star-studded line-up featuring Martha Stewart, Josh Brolin, Jim Gaffigan, Tiffany Haddish, Evie McGee Colbert, Amy Sedaris, Ben Stiller, Aubrey Plaza, “Weird Al” Yankovic, and James Taylor, all facilitated by journalist John Dickerson. In a reversal of roles, Colbert found himself in the hot seat as his friends posed questions designed to delve deeper into his personal preferences and experiences.
Kicking things off, Billy Crystal asked Colbert about his ideal sandwich, to which the host declared Katz’s Deli’s hot pastrami as his top choice. The light-hearted banter continued, with Brolin inquiring about the scariest animal the host had ever encountered. The actor surprising Colbert with a ship in a bottle, wishing him well on life’s journey.
Stewart took a moment to reflect on the bittersweet occasion, expressing her happiness of being on the show but also sadness at its approaching end. When she asked Colbert whether he preferred apples or oranges, he leaned towards apples without hesitation, showcasing his preference in a charmingly straightforward manner.
As the segment progressed, Mark Hamill posed a playful query, asking if Colbert had ever sought a celebrity’s autograph. The host reminisced about a moment with Steve Martin, a figure whom he deeply admires. Colbert recounted how Martin signed a painting from his previous show, The Colbert Report, now prominently displayed in his office—a cherished keepsake he humorously dubbed “Steve Martin O’Clock”.
As the curious questions continued, guests prompted Colbert on topics ranging from the afterlife to his cinematic tastes. He identified “Raiders of the Lost Ark” as his favourite action film, showcasing his affinity for classic cinema. Plaza, in her typical comedic fashion, joked about being in a precarious situation but still managed to pose a significant question, asking Colbert whether he preferred cats or dogs; he revealed his allegiance lay with dogs.
The segment culminated with Dickerson’s poignant final question, asking Colbert to summarise the rest of his life in five words. The host responded with “My family, my friends, fun,” to which Dickerson responded warmly, “God bless you, Stephen Colbert,” encapsulating the camaraderie shared between the host and his illustrious guests.
This gathering of stars occurred just one day before Colbert was scheduled to conclude his show, which he had hosted since taking over from David Letterman in 2015. CBS announced the show’s cancellation earlier in July 2025, following Colbert’s outspoken criticism of the network’s parent company, Paramount, regarding a controversial settlement involving former President Donald Trump.
Reflecting on his long tenure, Colbert shared his thoughts with PEOPLE, acknowledging the challenges of maintaining such a demanding role. “You have to think about, well, when is the right time to end your tenure? I didn’t think this soon, but who knows? Maybe CBS saved my life,” he said. He expressed gratitude that stepping down would allow him to reserve energy for future endeavours.
As the curtain closes on The Late Show, Colbert leaves behind a significant legacy, marked by his distinctive humour and ability to connect with both guests and audiences alike. His impact on late-night television, characterised by sharp wit and heartfelt moments, will undoubtedly be felt for years to come.