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Late Show Five Reunite For Stephen Colbert Goodbye

Originally posted on Total Apex Entertainment
By David Gilbert | Last updated May 9, 2026 7:21 PM ET

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Stephen Colbert has assembled an all-star lineup of late-night hosts as some of his final guests on “The Late Show,” which wraps up on May twenty first after CBS canceled it last year. Jimmy Fallon, Jimmy Kimmel, Seth Meyers, and John Oliver will all appear on May eleventh for what promises to be a reunion filled with jokes, memories, and probably a few inside jabs at the network.

David Letterman Built Late Night Institution First

The four hosts previously joined Colbert in 2023 to co-host a podcast called Strike Force Five during the writers and actors’ strikes. Have you ever seen so many late-night personalities in one room that you wondered if the studio could contain all that ego?

“The Late Show” brought these five together before for a good cause, raising money for crew members who went without pay during the work stoppage. Now they return to say goodbye to Colbert, who has held the desk since 2015 after taking over from the legendary David Letterman. “The Late Show” originally launched with Letterman at the helm, and he will stop by on May fourteenth to chat with the man who replaced him.

David Letterman hosted Late Night on NBC from 1982 to 1993 before moving to CBS and building “The Late Show” into a late-night institution. Letterman handed the reins to Colbert upon retiring in 2015, and now he returns to watch his successor sign off for the final time. “The Late Show” will also welcome other famous faces during its final weeks, including John Krasinski, Julia Louis Dreyfus, Pedro Pascal, and Tom Hanks.

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A person has to wonder whether Tom Hanks will cry during his appearance, because that man tears up at everything from “Toy Story” endings to late-night goodbyes. “The Late Show” has packed its remaining episodes with special segments, including a Kids Pitch segment featuring Jenny Slate, Liam Neeson, John Oliver, and several others. A Broadway performance will showcase Annaleigh Ashford, Christopher Jackson, Bernadette Peters, Ben Platt, and Patrick Wilson, because nothing says farewell like show tunes.

“The Late Show” will also air a Colbert Questionnaire taken by Barack Obama, which should provide plenty of thoughtful answers mixed with the former president’s signature dry wit. The Strokes will perform, giving the show a rock and roll send-off that feels appropriate for a host who loves music almost as much as politics. “The Late Show” cancellation news broke back in July 2025, with CBS citing a financial decision that many people still do not buy.

Trump Celebrated, Fans Smelled Censorship

Stephen Colbert in an episode from “The Colbert Report”, Courtesy of Paramount Media Networks/Comedy Central

Prominent voices have called the cancellation an act of censorship because the move came during a period when parent company Paramount sought approval from Donald Trump’s FCC for its sale to Skydance. “The Late Show” hosted a host who frequently criticized Trump, and Trump repeatedly celebrated the show’s cancellation, which made the financial excuse feel flimsy at best. David Letterman, never one to hold back, recently called CBS executives lying weasels in an interview with a New York Times journalist.

Letterman went further, claiming that Colbert got dumped because the people selling the network said they would take care of the show and throw it into the deal. “The Late Show” cancellation looks less like a business decision and more like a political one, according to Letterman and many other observers. A person has to ask whether CBS will ever admit the real reason they ended one of the most popular late-night shows on television.

“The Late Show” concludes on May twenty first after a decade of monologues, sketches, and interviews that defined late night for a generation. Stephen Colbert brought a unique blend of satire, earnestness, and intelligence to a format that sometimes favors easy jokes over meaningful conversation. “The Late Show” will be missed by fans who appreciated a host willing to call out hypocrisy and silliness in equal measure.

Late Night Feels Different Forever Now

So that leaves late-night fans with a bittersweet farewell and a stellar lineup of guests saying goodbye. Stephen Colbert welcomes Jimmy Fallon, Jimmy Kimmel, Seth Meyers, and John Oliver on May eleventh, then David Letterman on May fourteenth. “The Late Show” packs its final episodes with celebrities, musical performances, special segments, and probably a few tears from the host himself.

CBS called it a financial decision, but most people see it as something else entirely. “The Late Show” ends not because it failed, but because the people in charge wanted it gone. Stephen Colbert walks away with his head held high, and the viewers walk away wondering what might have been. “The Late Show” signs off on May twenty first, and late night will never feel quite the same.

This article first appeared on Total Apex Entertainment and was syndicated with permission.

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