As part of the introduction to a Sunday-night conversation between Stephen Colbert and Conan O’Brien, New Jersey governor-elect Mikie Sherrill promised attendees “the entertainment event of a lifetime”—and the oftentimes-hilarious 90 minutes that followed kinda came close.
At Montclair Film’s “An Evening With Conan O’Brien and Stephen Colbert,” which was held at the Performing Arts Center (NJPAC) in downtown Newark, N.J., Colbert as interviewer invited O’Brien to revisit his early days as a comedy writer (including his time running The Harvard Lampoon as a mere sophomore), as well as his 28-year run across NBC’s Late Night and TBS’ Conan.
The late-night vets— who’d conversed as recently as a late-September edition of CBS’ The Late Show—engaged in electric banter fraught with faux, friendly friction, starting with Colbert clarifying that O’Brien is not from “Boston” per se but Brookline. “This is like a rectal exam!” groused O’Brien early into the back-and-forth. “What is this, 60 Minutes?!”
“You’re not even listening to me…,” O’Brien moments later sniffed. “This is a job interview that’s not going well!”
When Colbert at one point didn’t play off of O’Brien’s funny observation about the cavernous hall they were playing at NJPAC, the latter quipped, “You have no joy.” Colbert responded by rising from his chair on the well-dressed stage and sauntering over to a nearby bar set to pour drinks for him and his guest. O’Brien in turn got up and, turning his back to Colbert, launched into an improv’d stage play.
“I know that you have your eyes on Rebecca!” O’Brien dramatically huffed.
Colbert peered up from the bar set to join in, “Or is it that Rebecca has her eyes on me?” Their on-the-fly play went on for a minute or so, eliciting much applause from attendees.
In addition to the funny moments created by the longtime friends and peers—including dueling versions of why O’Brien didn’t hire Colbert as a writer for Late Night, and a rather detailed pitch for a Hallmark Christmas movie starring them as rivals for a woman’s heart—moving anecdotes were also shared.
O’Brien recalled how upon meeting the late John Candy, who’d been lured to Harvard to accept a made-up honor from the Lampoon, he was delighted to discover that his idol was “everything you wanted him to be, and 30% more.”
Colbert shared a story about how he and guest Steve Martin collaborated on a Late Show bit that culminated in the actor reprising the famous, “Well, excuuuse me!” line from his standup days of yore. Martin, though, genuinely worried it wouldn’t land. “What if it was never funny?” the comedy legend reportedly fretted.
Colbert and O’Brien also surveyed the state of the late-night space that the latter once called home and the former will involuntarily vacate in May 2026, due to Late Show’s cancellation.
“[I] am sad about this form,” O’Brien said. “[But] I am a 52% optimist and I believe that humans find a way, and really fine people who are 15, 16, 17, 20, 25 right now are going to use what’s available to make beautiful, hilarious, funny things…. I have to believe that.
“It will not look the same way as our path, it will not be the same path,” he told his host, “but it will be more or less the same idea.”
As for Colbert’s future specifically, O’Brien is already on record as believing that his peer is destined to “shine brighter” than ever before. But he reiterated his stance on multiple occasions during their Sunday-night sit-down.
“One of the first things I said to you when this [Late Show cancellation] news broke is there isn’t a person on this planet who’s worried about Stephen Colbert,” O’Brien shared. “These shows are a way for Stephen Colbert to relate to people but they are not the way.
“There are so many different things that you can do, and you’re going to do that are they going to give you enormous amounts of pleasure, and you’re going to be great at it,” he avowed. “You’re just not there yet, you haven’t begun that yet.”
The event closed with a round of audience questions, one of which led O’Brien to tell Colbert this: “There’s no better person I could be sharing the stage with right now. The world is your f**king oyster” and what Colbert does next “is going to be amazing.”
Please go back & edit this. The volume of typos makes it difficult to read. Please also update if we will be able to watch the event somewhere.
I am told that video will likely not be released, seeing as it was a fundraising event. Sorry!