For over a decade, Stephen Colbert has been a nightly staple for millions of viewers, his sharp wit and signature blend of political satire and celebrity banter helping to define CBS’s late-night landscape. But as the clock ticks toward May 21, 2026, Colbert’s tenure as host of The Late Show with Stephen Colbert is drawing to a close, marking not just the end of an era for him, but for late-night television as a whole. The final weeks behind the iconic desk are shaping up to be nothing short of a celebration—a gathering of comedy’s brightest, a reunion of old friends, and a nostalgic nod to the show’s storied past.
Colbert’s farewell run is packed with symbolism and star power. According to Variety and Entertainment Weekly, the last episodes will feature a parade of guests who have shaped both his career and the wider late-night universe. Perhaps the most anticipated moment is the appearance of David Letterman, the legendary host Colbert succeeded in 2015. Letterman, who helmed the show for an impressive 23 seasons, is set to return to the Ed Sullivan Theater—often affectionately called the “Letterman Theater”—on May 14, nearly 11 years after he passed the torch. As TV Guide’s Matt Roush put it, "David Letterman is going to drop by the theater where he reigned by something like 23 seasons. And so, that will be another moment of history when Letterman comes back to what we used to call the ‘Letterman Theater.’"
But Letterman’s return is just one highlight in a week brimming with late-night camaraderie. Colbert’s fellow hosts—Jimmy Fallon, Jimmy Kimmel, Seth Meyers, and John Oliver—will join him for what’s been described as a show of solidarity and a bit of late-night history. This group, dubbed the “Strike Force Five,” famously came together during the 2023 Hollywood writers’ strike, launching a podcast to support their out-of-work crews. Their reunion on Colbert’s stage is both a nod to that moment of unity and a testament to the tight-knit nature of the late-night community. As Roush noted, "They were all part of the ‘Strike Force 5’ podcast that they formed during COVID when the shows were shut down, and they all got together bonding on this podcast and raising money for their crews who were out of work."
The guest list for Colbert’s final weeks reads like a who’s who of Hollywood and beyond. Tom Hanks, Pedro Pascal, Julia Louis-Dreyfus, John Krasinski, Billy Crystal, and Ina Garten are all slated to make appearances, ensuring the show’s send-off is as star-studded as it is sentimental. Musical performances from The Strokes and Broadway icons Bernadette Peters and Ben Platt will add a celebratory note to the proceedings. In a particularly personal touch, Colbert will also feature a “Colbert Questionert” segment with former President Barack Obama—a fitting bookend for a host whose tenure has often intertwined with the nation’s political and cultural pulse.
Colbert’s journey to the desk began on September 8, 2015, when he stepped in following Letterman’s retirement. Before that, he’d carved out a unique space in comedy with The Colbert Report, where his satirical take on conservative punditry became a cultural phenomenon. Over 11 seasons at CBS, Colbert evolved The Late Show into his own, blending incisive political commentary with celebrity interviews and candid storytelling. He wasn’t afraid to break the mold—broadcasting remotely during the COVID-19 pandemic, poking fun at politicians from across the spectrum, and, of course, riffing on the quirks of American life.
One city that found itself in Colbert’s comedic crosshairs more than once was Sheboygan, Wisconsin. As reported by the Sheboygan Press, the city became a recurring punchline on The Late Show, whether as part of a “funny name towns” bit or in jokes about presidential campaign stops and crowd reactions. In December 2024, Colbert quipped about the arrest of Luigi Mangione in Altoona, Pennsylvania, lumping Sheboygan in with other humorously named towns. “Classic bad guy mistake,” he joked. “Fleeing to one of America’s funny name towns. Police will always find you right away, whether it’s Altoona, Pennsylvania, Rancho Cucamonga, California, or Sheboygan, Wisconsin.” He even playfully addressed his audience: "We have some native She-boingers here tonight."
Colbert’s jests didn’t stop at geography. During the 2024 presidential campaign, he poked fun at Donald Trump’s “horrible city” remark about Milwaukee, cheekily warning against dissing the city and joking, “The Paris of Wisconsin. Suck it, Sheboygan.” In another bit, he referenced Trump’s rally in Racine and the movie Jaws, with a shark attack scene dubbed, “I should’ve moved to Sheboygan!” Colbert’s humor even extended to President Joe Biden’s “Bidenomics” speech in Philadelphia, drawing a laugh by comparing the tepid crowd response to a tough room in Sheboygan and riffing on travel times from Sheboygan to Milwaukee. The city’s frequent mentions were so notable that Sheboygan’s mayor sent Colbert a care package and invited him to visit—a testament to the show’s cultural reach and Colbert’s knack for weaving local color into national conversation.
Yet, as the final curtain falls, the reasons for The Late Show’s end are as much a part of the story as the farewell itself. CBS has cited financial pressures as the primary cause for the show’s cancellation after an impressive 33-year run. Reports from Entertainment Weekly suggest the network was losing upwards of $40 million a year on the production, a staggering figure even by big-network standards. However, the decision has not been without controversy. Some industry watchers have speculated about the influence of Skydance Media’s acquisition of Paramount Global, CBS’s parent company, and whether new leadership sought to avoid political entanglements—especially with Colbert’s pointed takes on figures like Donald Trump.
David Letterman, never one to mince words, called out CBS’s official explanation in a recent New York Times interview: “I’m just going to go on record as saying: They’re lying,” he said. “Let me just add one other thing... They’re lying weasels.” His comments have fueled debate over whether Colbert’s departure is truly about dollars and cents or something more complex.
The end of The Late Show with Stephen Colbert leaves a question mark hanging over the future of the Ed Sullivan Theater, a venue steeped in television history. As Matt Roush put it, “It’s such a historic venue. I can’t imagine they won’t use it for something.” From Beatles performances to decades of late-night laughter, the theater has seen it all—and it’s hard to picture Broadway without its glow.
As May 21 approaches, viewers are bracing themselves for Colbert’s final bow. The host’s blend of humor, heart, and cultural commentary has left an indelible mark on late-night TV. While the lights may soon dim on Colbert’s run, the laughter—and the legacy—will echo for years to come.