As The Late Show with Stephen Colbert approaches its final episode on May 21, CBS is turning the show’s closing stretch into something far bigger than a routine sign-off. What initially began as the winding down of another late-night institution is now starting to feel like a celebration of an entire era of television.

Over the next few episodes, Colbert’s stage will become home to a rare gathering of comedy personalities, longtime collaborators, Hollywood stars, and figures who helped define the show across its decade-long run. The final few weeks are being structured less like a farewell tour and more like a retrospective journey of modern late-night television itself. That emotional weight has only intensified because of the circumstances of the show’s cancellation, which has remained heavily debated across the entertainment industry, especially given Colbert’s status as one of television’s most outspoken political comedians.

And now, as the finale is inching closer, the names joining Colbert during these final episodes are making the sendoff feel even bigger.

Among the biggest names that are set to appear before the finale are Jimmy Fallon, Jimmy Kimmel, Seth Meyers, John Oliver, and David Letterman himself. All of them are scheduled to appear together on May 11 as per Paramount's official press release, reuniting with Colbert after the group famously collaborated on the podcast Strike Force Five during the 2023 Hollywood strikes. The podcast raised money for crew members affected by the Writers Guild and SAG-AFTRA shutdowns.

Meanwhile, David Letterman’s appearance on May 14 carries even greater emotional resonance for the fans, as Letterman was the one who originally launched The Late Show on CBS in 1993 before handing the franchise to Colbert in 2015, following his retirement. This reunion feels like a full-circle moment for one of television’s most recognizable late-night brands.

The final weeks will also feature appearances from stars including Tom Hanks, Pedro Pascal, Julia Louis-Dreyfus, and John Krasinski, alongside musical performances and special segments involving Barack Obama, Broadway performers, and rock band The Strokes.

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While audiences online have already begun treating the upcoming episodes like an event, the farewell run also arrives amid continued debate surrounding CBS’s controversial cancellation of the show last year.

Since taking over The Late Show in 2015, Stephen Colbert has transformed the program into one of the defining voices in modern late-night television. During his tenure, the show earned more than 50 Emmy nominations, multiple wins, including Outstanding Talk Series in 2025, and consistently remained among the highest-rated programs in the format.

The show’s cancellation sparked backlash almost immediately after CBS described it as a financial decision. Critics, including David Letterman, publicly questioned the reasoning behind the move, especially as Paramount pursued regulatory approval tied to its Skydance merger.

For Colbert himself, the ending has also become unexpectedly personal. Speaking to The Hollywood Reporter, he admitted that after learning about the cancellation, some of the only people he spoke with for days were Fallon, Kimmel, Meyers, and Oliver — a reminder of how closely connected the late-night world remains behind the scenes.

And as The Late Show heads into its final episode, these upcoming reunions feel less like standard guest appearances and more like late-night television gathering together for one last curtain call.

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Which guest appearance are you most excited to see during Stephen Colbert’s final weeks on The Late Show? Let us know in the comments.