Late-night hosts like to play games with their guests in order to uncover a different side of them (see: Seth Meyers’ Day Drinking segment). And on January 9, 2021, The Late Show With Stephen Colbert launched “The Colbert Questionert,” during which Colbert asks A-list celebrities a series of 15 questions to get to know them on a deeper level.
Tom Hanks and Meryl Streep were the first two names to participate, via Zoom. Hanks surprised Colbert with an impromptu rendition of The Go-Go’s “Our Lips Are Sealed,” which was the Oscar winner’s choice for the one song he’d listen to for the rest of his life.
Since then, Colbert has given the Questionert to dozens of guests including George Clooney, Jane Fonda, Arnold Schwarzenegger, Barbra Streisand, Cate Blanchett—who lied supine on Colbert’s desk—Carol Burnett, Ringo Starr, Daniel Craig, and fellow late-night stars Jon Stewart, John Oliver, and David Letterman. On Thursday night, Billie Eilish became the latest Questionert inductee.
On a March episode of The Late Show Pod Show podcast, Colbert admitted that he doesn’t remember exactly who came up with the idea for the Questionert, but that guests seem to enjoy it.
Colbert referred to the segment as “a metaphysical rollercoaster… Only four questions later you’re asking what happens when we die,” he told his podcast producer Becca Winer. It was, in fact, that very question that partly led to the creation of The Colbert Questionert in the first place.
In 2019, Keanu Reeves was guesting on The Late Show when Colbert asked the John Wick actor: “What do you think happens when we die?” After taking a beat, Reeves delivered a very thoughtful response: “I know that the ones who love us will miss us.” The exchange went viral, and got Colbert thinking about ways to regularly play with a more spontaneous line of questioning.
“We kind of owe it to Keanu Reeves for taking a moment and giving a thoughtful, simple, heartfelt answer that moved people,” Colbert said of the segment’s genesis. Because it was the reaction to Reeves’ answer that got the host wondering: “Can we build something around that?”
Three years later, during Reeves’ January 13, 2022 Late Show appearance, the actor officially took The Colbert Questionert. When it came to the death question, Colbert reminded Reeves of his original answer and asked the actor if he wanted to amend his earlier response in any way; he did not.
Not all the questions are that deep (or dark). The first question, for example, is always: “What’s your favorite sandwich?”
When Ryan Gosling took The Colbert Questionert on May 10, 2024, he made waves by declaring an ice cream sandwich as his favorite sandwich. “Do you lick around the edges?” Colbert asked him. “That’s none of your business,” Gosling responded.
Even though the guests know what the questions will be, they sometimes give wild responses. For instance, in response to whether Streep had ever asked for someone’s autograph, she shared that when she was 12, Richard Nixon autographed her Milky Way wrapper.
During Matt Damon’s Questionert, Colbert asked about his earliest memory, and Damon talked about a dream he had about his dead father and how he felt his love and protection. He also told an amazing story about adopting a jungle cat in Costa Rica and how, despite a brain tumor, the cat has survived on steroids.
For the most part, the 15 questions—ranging from whether the guest prefers a window or aisle seat on a plane to describing the rest of your life in five words—have stayed the same, though they dropped “the most used app on your phone” query. The one question every single guest gets wrong is: “What number am I thinking of?” (Colbert told Winer he won’t reveal what number he’s thinking of.)
As for whether Colbert would ever take his own Questionert, he says he would—but only once he has decided to end his time behind The Late Show desk. “That’s my tell,” he said.
