Stephen Colbert has assembled a string of marquee guests — including a Strike Force Five reunion and David Letterman — as The Late Show nears its May 21 finale
The final stretch of The Late Show on CBS has become a countdown filled with high-profile appearances. As the program approaches its scheduled finale on May 21, producers have lined up a roster of celebrated hosts and actors to appear across the remaining episodes. Among the most talked-about events is a one-night reunion of the late-night collective known as Strike Force Five, while another milestone visit will bring the show’s founding host, David Letterman, back to the Ed Sullivan Theater stage on May 14. These planned bookings underscore both the camaraderie of current hosts and the network’s high-profile sendoff for Colbert.
In the week leading up to the finale, Stephen Colbert is expected to welcome multiple heavy hitters. Reports indicate that on May 11 Colbert will host a rare in-person gathering of Strike Force Five — the group made up of Jimmy Fallon, Jimmy Kimmel, Seth Meyers and John Oliver — marking the first occasion the five have shared the same late-night stage. That same week, David Letterman is scheduled to appear on the Thursday episode. In addition to these reunions, the lineup features acclaimed performers such as Julia Louis-Dreyfus and Tom Hanks, and recent appearances have included former President Barack Obama. The network’s plan seems aimed at balancing nostalgia, star power and the bonds that have defined this era of late-night television.
The Strike Force Five reunion carries significance beyond celebrity spectacle. Originally formed during the 2026 writers strike as a charitable podcast to support out-of-work staffers, the series began as informal Zoom check-ins that evolved into a top-charting listening experience. That improvised chemistry showcased how this generation of hosts often prioritizes mutual support over old-school rivalry. Bringing all five to the Ed Sullivan Theater on the same night not only serves as a reunion but also highlights how late-night production has been reshaped by shared causes and collaborative projects in recent years.
Because several late-night programs have adjusted their schedules around these guest appearances, the Monday night episode with Strike Force Five could leave The Late Show as the only new network late-night broadcast that evening. Sources note that both Jimmy Fallon and Seth Meyers modified their taping plans for the week, while Jimmy Kimmel — who records in Los Angeles — was already expected in New York for Disney’s upfront presentation. These timing choices amplify the sense that Colbert’s final weeks are being treated as a moment for the entire late-night community.
As the series winds down, Colbert has been candid about his reaction to the network decision. He discussed the cancellation and the emotional aftermath in interviews and in a cover story conversation, describing a small circle of fellow hosts as the people he reached out to first. He relayed texts and reactions from peers — including quips about award campaigns and stunned messages from longtime colleagues — that capture how personal and industry-wide the moment felt. Meanwhile, the decision by CBS to end the show last summer remains a focal point of discussion, with public remarks from figures such as David Letterman — who has criticized the network’s handling of the cancellation — keeping the conversation in the headlines.
The final episode on May 21 will serve a dual purpose: it’s both a farewell to a single program and a snapshot of a transitional moment in broadcast late-night television. The careful curation of guests — blending iconic alumni, activist-driven reunions and A-list visitors — is intended to honor the show’s legacy while acknowledging the shifting economic and creative landscape that led to its end. Whether viewers tune in for a sense of closure, for a rare onstage gathering of late-night peers, or simply to see how Colbert signs off, the closing week is framed as a communal and consequential event.
In short, the closing chapter of The Late Show is being treated as more than a single-host goodbye. It has been constructed as a communal moment that highlights the friendships, industry upheavals and cultural rituals that define contemporary Late night. With appearances from the likes of Strike Force Five, David Letterman, and numerous headline guests, the remaining episodes preceding May 21 promise to be both reflective and talk-show theatrical — a staged conclusion designed to underscore how this era of television supported one another through uncertain times.