For more than five years, Stephen Colbert has been asking a set of 15 questions to some of the biggest names in entertainment—Tom Hanks, Meryl Streep, George Clooney, Barbra Streisand, and about 80 others.
He’s gotten answers about sandwiches and smells, action movies, and the afterlife. He’s heard guests sing, stall, confess, and occasionally spiral. And he’s gotten an answer—almost every time—to The Colbert Questionert’s most mysterious prompt: “What number am I thinking of?”
Some of the guesses have been tossed off quickly, others offered with mock seriousness, and a few have come after visible calculation.
Colbert has never confirmed that anyone’s got it right. But he has long promised that when his time on The Late Show ends, not only will he take the Questionert himself, but he’ll reveal the answer he’s been holding back all these years.
Now the payoff has a date. This Wednesday, May 20—the night before his final Late Show—Colbert is scheduled to take the Questionert himself, in a segment the show says will feature “special guests.” Colbert has previously said he’d have a friend administer the questions.
When The Late Show introduced the Questionert in 2021, it was, at least on its face, a simple concept designed to loosen up A-list guests and reveal something a little more personal than the usual press-tour anecdotes—with Tom Hanks as its first participant. Colbert described it as a way to get to know people on a more universal level, sidestepping the familiar rhythms of plugging projects in favor of questions anyone might have an opinion on.
But the structure is what made it stick. The same 15 questions—more or less (four have been retired and replaced over the years)—asked in the same order, over and over again. A best sandwich. A least favorite smell. Apples or oranges. Then, without much warning, a turn toward the existential: “What do you think happens when we die?”
Colbert has called it a “metaphysical roller coaster,” and the description fits. What begins as a parlor game gradually reveals itself as something closer to a ritual—one that invites comparison and rewards spontaneity, even as guests have grown more prepared for it.
Over time, the Questionert has become a kind of late-night badge of honor, reserved for guests of a certain stature and designed to produce moments that travel beyond the broadcast. Its origin story only reinforces that idea: the segment was inspired, in part, by a 2019 Late Show exchange with Keanu Reeves, whose brief, thoughtful answer to a question about death went viral and stuck with Colbert as something worth building on.
As for the only question on the list with a right or wrong answer, Colbert has given a few hints over the years.
He confirmed to Billie Eilish that it’s been the same number all along. He told Nicki Minaj that the number is between 1 and 100, and he told Josh Brolin that it’s a whole number. He revealed to Barbra Streisand that it’s an odd number, and told Sting that the answer divides into 18. Perhaps most tellingly, he’s responded “no” to every number guessed but one—to which he’s repeatedly responded “interesting.”
That’s left some observers convinced that they know the answer—and they very well may—but there’s also reason to believe Colbert has been enjoying the misdirection.
After all, a mystery only works if it lasts.
On Wednesday night, the Questionert’s one lingering question will finally meet the only person who can settle it.
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