Stephen Colbert has lined up David Letterman for Thursday during the penultimate week of The Late Show, setting up a farewell stretch that starts tonight and leans hard on familiar names. The Strike Force Five will also appear Monday night as Colbert moves toward the end of his run.
Letterman is not just another guest. He created The Late Show, and his return gives Colbert’s final weeks a kind of full-circle feel that fits the scale of the moment. For a host who has spent years calling the Pope and his predecessors his dream booking, the booking of Letterman is the rare one that actually landed.
That missed holy grail has been part of Colbert’s late-night identity for years. He has repeatedly called the Pope his dream booking, and he has implied that he has made the big ask without success. No positive smoke signals from the Vatican have ever emerged, leaving the request in the realm of a running joke as much as a serious ambition.
For now, though, Colbert has something concrete to work with. The penultimate week on The Late Show begins tonight, Monday brings the Strike Force Five, and Thursday brings Letterman, the man whose show Colbert is helping carry to its finish. It is the kind of guest list that turns a goodbye into an event, even before the final broadcast date in 2028 comes into view.
The contrast is hard to miss. Colbert can secure the creator of the show for a farewell appearance, but not the Pope he has chased for years. That leaves his closing run with a sharp and oddly fitting shape: the host gets one of late night’s defining figures, while the one booking he has treated as a joke, a wish and a challenge remains out of reach.
