The Newark venue was electric Sunday night, packed to the rafters of a grand, sold-out performing arts center, and the audience clearly felt the influence of a family-first moment. Stephen Colbert of The Late Show sat with Conan O’Brien, a longtime late-night staple, as part of Montclair Film’s charity event—an evening that also highlighted Colbert’s wife Evelyn Colbert, who leads the film organization's board.
Colbert opened up about his childhood, describing himself as the youngest of 11 children who always found his siblings hilarious, even if his storytelling fell flat. He recalled a memory of his mother defending his stories to the groaning crowd, saying, “You listen to his stories; it matters to him.” The takeaway, Colbert adds, is a simple one: when someone enjoys your storytelling, it’s a sign that your mom’s influence has left a lasting mark.
For two decades, Colbert, now 61, has been behind a desk weaving narratives that have entertained millions. But the next chapter unfolds in May 2026 when Colbert’s current run ends. The announcement that The Late Show would go off the air followed a broader controversy: CBS’s parent company Paramount settled for $16 million in connection with a dispute tied to Donald Trump amid its $8 billion merger with Skydance. Though the onstage discussion didn’t name the president, the undercurrent of change loomed over the night. Even New Jersey Governor Phil Murphy acknowledged the moment, joking that he wanted to be there to compare notes with Colbert as both faced transitions.
O’Brien, who spent years hosting Late Night, The Tonight Show, and Conan, offered Colbert some candid guidance—incisively wrapped in his characteristic mix of humor and humility. Since leaving his show in 2021, O’Brien has often reflected on the fact that television hosting is not the sole measure of impact; it’s a platform, not the only path. He urged Colbert to recognize that many other avenues exist to create joy and meaningful work, and that Colbert’s future projects could be equally rewarding even if they look different from his late-night persona.
The duo even teased a playful, tongue-in-cheek idea: a gloriously self-serious Hallmark-style Christmas film in which O’Brien portrays an ambitious figure who initially mocks the idea of a holiday miracle, only for life to lead him to a candy-cane factory run by Colbert and his three daughters—Tinsel, Holly, and Popcorn String—injecting a bit of whimsy into the fantasy.
As Colbert reflected on leaving late-night TV after more than 20 years, he mourned the loss of a longstanding American entertainment staple. He and O’Brien agreed that what they miss most are shows that evoke the vaudeville-era flavor of early television—where performance, wit, and live audience energy came together in a distinctly intimate, communal experience. Colbert emphasized his affection for the people he collaborates with and the work he loves, while also acknowledging a sense of sadness for a format that seems to be dwindling, leaving fewer venues for that particular kind of shared moment.
But the conversation wasn’t just about endings. The overarching message was one of possibility: a future rich with diverse creative outlets that can bring just as much pleasure and success as late-night television. And with that, the question remains: what new forms of storytelling will rise to fill the gap, and which path will Colbert choose next to keep connecting with audiences in surprising, innovative ways?
