How Will Stephen Colbert End ‘The Late Show’? ‘It’s Going to Be Very Unusual’

TV finales often elicit weeks, if not years, of speculation about how they’re going to end. “The Late Show with Stephen Colbert” is slightly different, not only because it’s a late-night show — rather than a serialized story with character arcs to resolve and twists to land — but because much of the focus leading up to Thursday night’s final episode has dwelled on bigger questions.

What does losing a 33-year-old staple of television mean for the late-night format going forward? What do the circumstances surrounding its cancellation — in which CBS appeared to sacrifice Colbert at the alter of the Trump administration in order to ensure the Paramount-Skydance merger was approved — tell us about the public’s depleting trust in traditional media, as well as their declining faith in the First Amendment? Plus, what will Colbert do next — you know, besides write a new “Lord of the Rings” movie?

On Thursday, don’t expect the second and last host of “The Late Show” to look so far ahead. Instead, much of what happens when Colbert says goodbye could be rooted in the past, paying homage to those who came before him, as well as those who’ve toiled alongside him for nearly 11 years in the Ed Sullivan Theater.

One thing’s for sure: He’s not going to repeat himself.

Journalist, historian, and late-night expert Bill Carter confirmed as much Wednesday evening at a panel presented by the Paley Center for Media that revisited the best finales in late-night. Carter, who wrote the bible of late-night TV books, 1994’s “The Late Shift,” as well as its acclaimed 2010 follow-up, “The War for Late-Night,” was responding to a question about Colbert’s finale for “The Colbert Report,” when the in-character host invited an impossible number of guests onto his tiny studio stage for a closing sing-a-long set to Vera Lynn’s “We’ll Meet Again.”

“After seeing that, as we’re looking ahead to his exit,” curator Jason Lynch said, “do you think he’ll be able to top the number of cameos he had then?”

“No, he’s not going to attempt that,” Carter said. “I have a sort of idea of what he’s going to do. It’s going to be very unusual.”

When Lynch tried to move on, a member of the crowd shouted, “Oh, come on! You’ve got to tell us more than that.”

“Are you kidding?,” Carter said. “They would drum me out of the late-night brotherhood.”

Nevertheless, in their preceding presentation, Carter and Lynch provided plenty of ideas for what could be included in the last “Late Show,” as well as what those choices tell us about the hosts, their work, and their legacies.

“I want [the last episode] to be funny,” Carter said. “I really think that an effort should be made not just to say goodbye, but to do it in a creative way. And the best hosts have done that. They’ve found ways to have the emotion and the farewell aspect, but also to play with it and have some fun with it.”

Here are a few more highlights from the past that may resurface in our immediate future:

The “Poignant Goodbye Song”

On May 22, 1992, Johnny Carson invited guests to “The Tonight Show” for the last time. One of those guests was Bette Midler, who sat on a stool, accompanied only by a piano, and sang “One for My Baby” directly to Carson. With intimate framings from over her shoulder, isolating the singer and the host like they were the only two people in the room, the moment was instantly iconic and spawned many an homage when Carson’s successors had to craft their own goodbyes.

“Interestingly, the Bette Midler [performance] set the idea of this serenade to sing the person off,” Carter said.

As noted above, Colbert ended “The Colbert Report” with a group song. Martin Short spoofed what Carter called the “poignant goodbye song” during the finale of “Conan,” when he tried to sing the same tune to Conan O’Brien that he sang to Letterman on “The Late Show.” (It was all in jest — one of many jokey goodbyes O’Brien concocted to keep the tone light.) “The Larry Sanders Show,” one of the great scripted comedies and an exacting send-up of the genre, even included a goodbye song in its finale courtesy of Jim Carrey belting out “And I’m Telling You I’m Not Going” from “Dreamgirls” (before the comedian told Larry off-air that he didn’t give a shit about him or his show — he was only there to promote his movie).

On the actual last episode of Letterman’s “The Late Show,” the host was surprised with a montage of series’ highlights (secretly put together over multiple months by executive producer Barbara Gaines) and set to the Foo Fighters’ “Everlong,” his favorite song. (And one that was especially significant, per Carter, because the band played the same hit when Letterman returned from quintuple bypass surgery in 2000.)

“It’s an extraordinary piece of work, actually,” Carter said of the montage. “The antithesis of sitting on the stool.”

‘The Late Show with Stephen Colbert‘Courtesy of Scott Kowalchyk / CBS

Which brings us to Carson’s heartfelt goodbye. Midler’s song wasn’t his last moment on “The Tonight Show” (it wasn’t even the last episode, but let’s come back to that). For his parting words, the landmark late-night host sat on a stool and addressed the audience and his colleagues directly.

“And so it has come to this,” Carson said. “I am one of the lucky people in the world. I’ve found something I’ve always wanted to do, and I’ve enjoyed every single minute of it. … You people watching, I can only tell you it has been an honor and a privilege coming to your homes all these years to entertain you. … I bid you a very heartfelt goodnight.”

Carson’s earnestness and staging set the bar for future hosts, and many have followed his lead down to his choice of chair.

When O’Brien was forced out of his dream gig on “The Tonight Show” in 2010, without knowing what he’d do next, he pleaded with his audience to resist giving into cynicism. During his goodbye from “Conan” in 2021, O’Brien sat on a stool, alone on stage, and defined his comedy by saying he always sought out the “strange phantom intersection between smart and stupid” before choking up with one more request of his fans: “So my advice to anyone watching right now, and it’s not easy to do, but try and do what you love with people you love, and if you can manage that it’s the definition of heaven on earth.”

When Jon Stewart first left “The Daily Show,” the big moving moment came courtesy of Colbert. Knowing how uncomfortable Stewart was with sincere expressions of gratitude, Carter said Colbert was prompted to surprise the exiting host with exactly that. On the day of the show, Colbert got cold feet and went to Stewart’s wife, Tracey Lynn McShane, for advice. “He’ll hate it,” Carter said, paraphrasing McShane’s reaction to the speech. “You have to do it.”

When he did and the speech was over, the correspondents rushed the stage and surrounded Stewart in a group hug, chanting, “You made him cry!”

And, of course, when Larry Sanders ended his fictitious talk show, he did so with a direct address to the audience while sitting on a stool. When he was done and his producer Artie (Rip Torn) came over to congratulate him, Sanders told him, teary-eyed, “I can’t get off the stool.” Then, to get the laugh, he added, “I can’t move my legs.”

The Finale That’s Not Really the Finale

Stephen Colbert and David Letterman on ‘The Late Show’Courtesy of Scott Kowalchyk / CBS

Nods to late-night history and sincere thanks may be inevitable in Colbert’s final hour — no matter how “unusual” it gets — but perhaps the most important thing to remember from past late-night endings is that the finale is a moment in time, not the moment in time.

Take, for instance, Carson’s last show. If you type “Johnny Carson and Bette Midler” into YouTube’s search bar, it automatically fills in “last show.” But Midler’s performance wasn’t during Carson’s “Tonight Show” finale. It came the night before, in his penultimate episode. Our collective memory puts her at the end because the memorable scene provided such a perfect goodbye. It just fits, reflecting the powerful connection late-night hosts can share with viewers.

“One of the least talked-about aspects of these late-night shows is that they’re on late at night — or, at least, they used to be — so people often watch them in bed, and they develop a friendship, a connection with the host,” Carter said. “So when those people say farewell, it’s like they’re losing a friend. They’re not going to hang out anymore. It’s meaningful to them. Very often, it’s emotional for them. I think it really is a deeper connection that most television creates.”

Those kind of connections elicit memories that extend beyond one hour, one night, and one show. O’Brien’s “Tonight Show” exit ran for two weeks worth of shows before his last episode. Stewart and Letterman had even longer roads to the finish, and Carter argued Letterman’s recent visit to the old stomping grounds may end up being what we all remember about Colbert’s final days on “The Late Show” — a fitting final impression, given they were the only two men to sit behind the desk.

“He was fantastic on Colbert last week,” Carter said of Letterman. “That’ll be the Bette Midler episode. They’ll think that was the finale.”

Although the actual finale will certainly try to go out on top, there’s no telling what fans will think of when remembering “The Late Show’s” end. It’s been 10 months since CBS announced the cancellation, and Colbert has made 130 shows in the interim. Will those shows define his legacy? Was it already set before then? And what about what happens next?

“He’s a very, very talented guy, and a very deep and thoughtful guy — unusually philosophical and actually has a lot of faith in his life,” Carter said. “I know he wants to do more, I don’t think he perfectly has an idea of what it could be.”

Carter again looked to the past for insight into the future, pointing out Colbert’s origins before sliding behind a desk.

“He’s not really a stand-up comedian. He was an actor — he was a sketch actor, really, and that’s what he did: He did a sketch for nine years [on ‘The Colbert Report’], and it was amazing,” Carter said. “I would think he might do something more like that.”

And while his character from the Comedy Central series may be owned by a company unwilling to give it back to him (Paramount), there’s plenty more people he could bring to life in front of a live audience.

“He should do a one-man show on Broadway,” Carter said, before wrapping the panel with a nod to Colbert’s first highly anticipated adieu. “We’ll meet again some sunny day.”

We will. After one more night.

“The Late Show with Stephen Colbert” airs its final episode Thursday, May 21 at 11:35 p.m. ET on CBS and Paramount+.