Stephen Colbert's rise to the top: The Late Show host reflects on almost a decade in his dream job

Stephen Colbert is running out of wall space.

High above Manhattan on a warm April day, the Late Show host is giving Entertainment Weekly an impromptu tour of his office, spotlighting a few of his favorite oddities. The room itself overlooks Broadway from a top floor of the Ed Sullivan Theater, but with its wood paneling and mountains of memorabilia, it feels more like the cozy basement of your coolest (and nerdiest) uncle. Since inheriting the space from previous Late Show host David Letterman, Colbert has covered almost every inch of the walls with posters, historical ephemera, and his kids’ old art projects: There is Donald Trump’s impeachment resolution, signed by various congressmen and hanging right next to Richard Nixon’s. There’s a poster from the Philip Glass premiere where he first met his wife, Evie. And a pennant his mother brought back from the 1963 March on Washington, which she attended while pregnant with him. At the top of a bookshelf, he points out one of his prized possessions, a piece of the original Grey Havens model from The Lord of the Rings, given to him by director Peter Jackson and now lovingly protected under a glass dome. Near the door hangs one of his favorite images from the early days of The Late Show, a scientific drawing of two mating frogs that CBS forced him to blur on air. (The network later relented, as long as he captioned it as two frogs “tandem skydiving.”)

At one point, Colbert clambers onto the couch to access a high shelf, knocking pillows onto the floor. He reaches past an Emmy to grab what he was looking for: a golden trophy given to him by Olivia Wilde. “We had an ‘Act Off,’ and she said I acted harder than she did,” he says with pride. “So, she sent me an award.” It now resides in a place of honor, near the expired can of sausage his mother mailed him after he graduated college, a Bob Mackie sketch of Carol Burnett, and a cardboard Galactus helmet from Burger King (which he’d wear at The Colbert Report whenever he had writer’s block). 

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Back at his desk, he pulls out a framed photo of an early-career Walter Cronkite, from when the legendary news anchor used to discuss the day’s headlines with a Muppet-like lion named Charlemagne. “This is my reminder that Walter Cronkite started off as a morning anchor who had a puppet lion, so let’s not hear about the dignity of CBS News,” Colbert says with a grin. “F--- you.”

The Late Show With Stephen Colbert may not exactly be big on dignity, but boy, is it big. Since launching in 2015, Colbert has catapulted the series to record ratings, transforming it into the most-watched show in late-night for eight consecutive seasons. Much of the show’s success stems from Colbert’s signature blend of silliness and satire. The 60-year-old comedian built his career first as a correspondent on Comedy Central’s The Daily Show starting in 1997 and then graduating to host of the beloved Colbert Report in 2005, before conquering network TV. Coming from the high-concept parody of his cable series, he says he initially bristled against the traditional late-night format, assuming he had to completely rethink and deconstruct one of the oldest forms of TV entertainment. But he quickly discovered that not only did he like hosting a late-night show, it felt like home. “I was determined to not do a monologue,” he admits of his initial approach to the show. “I thought, ‘I’m not a stand-up. I’m an actor.’ And then I fell in love with the monologue. You just need to relax, have a good time, and follow your instincts in terms of the stories you’re interested in.”

So far, those instincts have served him well. Over the past nine years, Colbert has seemingly perfected the ratio of absurdist political humor, insightful celebrity conversations, and dumb gags. At a recent episode taping in April, he kicked off the evening by poking fun at Trump’s Manhattan criminal trial, breaking down the convoluted legal process and describing the former president as “basically a hunk of beef jerky with a layer of bronzer.” But then, he pivoted to a much stupider topic: a group of Floridian monkeys that had recently tested positive for herpes. As he warned viewers not to “touch macaque,” his bottom lip quivered and he bit back giggles. “I love puns,” he tells EW with a shrug and a smile. “I love stupid jokes and stupid, stupid puns.”

Blending the stupid and the smart isn’t exactly new territory, but few comedians do it quite as well — or as seamlessly — as Colbert. That tonal flexibility is what’s helped cement him as one of the best interviewers in late-night, often leading his guests into thoughtful discussions on loss, faith, or politics. (It’s hard to imagine another late-night host reciting Shakespeare from memory with Denzel Washington or having a poignant conversation about grief with a teary Andrew Garfield.) 

He particularly loves asking his guests about their early jobs — whatever they did to survive before finding success. “There are some young people who got very successful very early, and obviously I wish them ill,” he deadpans. “But I love the people who had to suffer.” After all, he can relate. After studying theater at Northwestern University, he lived in a friend’s basement in Evanston, Ill., sleeping on a concrete floor. He paid his $50 rent by building cheap futon frames out of two-by-fours and drywall screws and selling them to broke college students. “They would fall apart in the middle of the night,” he recalls. “People would call me furious, and I would put a handful of screws in my pocket and [grab] a cordless Makita drill. I would ride my bike across Evanston, and I would fix their bed and go home.”

Eventually he scored a job answering phones and selling souvenirs at the legendary comedy institution Second City. A perk of the job? Free classes. And maybe it’s that improv background that makes him such a good listener who’s generally willing to let his guests take conversations in unexpected directions. “I’m not setting the tone,” he explains. “My interests are eclectic, and my tone is malleable. There’s almost nothing that we could talk about that I’m not going to find some interest in. I’m willing to ride your pony wherever.” The only exception is when he has politicians on his couch. “With politicians, I feel a different obligation to ask the questions that I want to ask, not the questions they want to be asked,” he explains. “It’s not like I want to be adversarial, but when you interview a politician, you can’t edit anything they want you to edit.”

Politics has been on his mind, especially with another election season looming. He notes that since starting with The Daily Show, this will be his seventh time covering a presidential race — and “it’s unlike any other presidential election year before.” Back with The Colbert Report and in the early days of The Late Show, he would gather his staff at the beginning of the primaries, telling them to enjoy the inherent comedic opportunities: “When the election’s going on, there’s this news story every day. Everyone pretty much knows what the story is. You don’t have to explain much to them. Everybody cares, and nobody dies.” But with the 2020 election, that changed.

“Everybody cared, but people did die — not just in the attacks on Jan. 6, but a million people died because of the negligence in the response to COVID,” he says. “So, this time around, the stakes are very high, and we’re having trouble agreeing on what the story is.”

If there’s one thing he’s learned from multiple election cycles, it’s to embrace live television. Live specials have become a staple of The Late Show’s election coverage, and for a week in August, the show will move production to Chicago, covering the Democratic National Convention. Colbert says he and his staff have come to relish the ticking clock. “That sense of urgency gets into the whole building, and it makes everybody get on their toes,” he explains. “The jokes are decidedly sharper.” Still, the stress is real. After filming a live show, the host often finds himself so wired that he can’t fall asleep for hours afterward, pacing around until 3 or 4 in the morning.

As the presidential election creeps closer, Colbert says he feels like most Americans: mainly a sense of uncertainty and apprehension about what the next few months will hold. “The polls all say that America’s looking at these two candidates and going, ‘Oh well. I wish I had other options,’ ” he says. “I’m not saying I wish I had other options, but fresh meat is always fun. But we’re going to do our best to braise these two tough old chickens until they’re tender enough to carve.” He’s also looking forward to an election season with his longtime friend Jon Stewart back on TV, and he’s been obsessively watching The Daily Show each Monday. Still, he’ll miss the long-running gag that Stewart spent his retirement living under Colbert’s Late Show desk. “If you know anybody who’s looking for a place to live, it’s fantastic,” Colbert offers. “It’s a one-bedroom. There are no windows, but it’s quite lovely.”  

At that April episode taping, Colbert takes the stage with a bouncing energy, locking arms with bandleader Louis Cato and skipping around like the Scarecrow traveling the yellow brick road. Each night, he warms up by chatting with the audience, and after the furious chants of “Stephen! Stephen! Stephen!” die down, he takes questions. How’s your wife, Evie? a woman asks. “She is just delightful,” Colbert responds, beaming. What’s your dream role? He’s always loved Judas in Jesus Christ Superstar, even if he readily admits that he’s wrong for the part. Who’s your dream guest? This is the question he gets the most, and right now, it’s probably Pope Francis. (Colbert, a lifelong Catholic, was recently invited to narrate the pontiff’s audiobook.)

As for other side projects? Throughout our conversation, Colbert continues to repeat his mantra that he’s an actor, not a stand-up comedian. Hosting hundreds of shows a year doesn’t exactly leave room for other endeavors, but might we see him on stage or screen anytime soon?  

“It’s not like I want to drop the hammer on this woodshed that we work in here and go run off back to the footlights,” he admits. “But if there’s something that I used to do that I don’t do anymore, it’s acting. I miss that.”

In the meantime, he plans to stay at the Ed Sullivan for as long as they’ll let him. One of the biggest joys of hosting The Late Show is how much he loves going to work on Broadway every day. The more time he’s spent there, the more he’s felt the building’s legacy. Now he can rattle off the theater’s history like a particularly knowledgeable CBS tour guide.

“I used to think one space is much like another space, and it’s what you fill it with,” he says, leaning back in his desk chair. “Which is true, because I’ve worked in other places, and I’ve had a good time in what are not-beautiful surroundings and not-historic locations. But I love the fact that this was built in 1927 by Hammerstein as a cathedral of culture. I love the fact that Archie Leach — [better known by his stage name,] Cary Grant — had his American debut on that stage in 1927. Or that The Honeymooners was shot here when it first started as part of The Jackie Gleason Show. I know where Elvis was standing when he sang, and I know where the girls were sitting when the Beatles played. I love it. It’s an honor to be in this space, and I try not to take that for granted.”

He loves every inch of the Ed Sullivan, from his wood-paneled office to the brass-handled elevator he takes to access the stage every day. The elevator has been there since the building’s construction, and Letterman taught Colbert how to operate it when he inherited the space. To this day, he can usually tell if it’ll be a good show based on whether he can perfectly land the elevator, lining up flush with the floor outside. “First time I landed it, I thought I did a pretty good job,” he says. “And Dave looked at it and he goes, ‘It’s not up to my standards.’ So every time I land the elevator on the floor, I think, ‘I wonder if that’s up to his standards.’ ”

He’s gotten pretty good, but even after years of practice, nailing it can be tricky: The cable tightens and loosens with the weather, and the speed depends on how many people are on board. There’s no exact science, he notes, just a gut feeling — making it not all that dissimilar to performing. “There’s a little bit of ‘Use the Force, Luke,’ ” he says with a laugh. “Except the Obi-Wan in my head is Dave.”