As soon as Stephen Colbert arrived on the set of his PEOPLE cover shoot at the historic Prince George Ballroom in New York City, he excitedly added a few funny ideas to the shot list: “What if I put my feet in the cake, not next to the cake?”

Colbert’s spirits were high, especially when he walked out in boxers for another set-up. “A little something for the ladies,” he quipped with the same humor and relaxed confidence he exudes every night as the host of The Late Show with Stephen Colbert.

After 11 seasons at the helm of the program (created in 1993 and originally hosted by David Letterman until 2015), Colbert, 62, will tape its last episode on May 21. In July 2025, CBS cancelled The Late Show just days after Colbert criticized the network’s parent company, Paramount, for its $16 million settlement with President Donald Trump. (Trump sued CBS’ 60 Minutes, accusing them of deceptively editing an interview with former Vice President Kamala Harris. At the time, Paramount was in the middle of a merger with the entertainment company Skydance, which required approval from the Trump administration.)

Despite leading the late-night ratings, CBS said cancelling The Late Show was “purely a financial decision” and “not related in any way to the show’s performance, content or other matters happening at Paramount.” When Colbert heard the news from his manager, he says he was lying down with a sock over his eyes, resting before the show: “I sat up and I said, ‘I’m sorry, I’m awake. Could you say that one more time?’”

Nine months later, Colbert is reflective and filled with gratitude as he describes his experience. “I tried never to take for granted filming in the Ed Sullivan Broadway theater, having that tremendous audience, or having the ability to work with the funniest people I know every day and make jokes about the things that make me most anxious.”

Now, he wonders if CBS “saved my life” because “it takes a lot of bone marrow to do the show every day, and now I’ll be stepping down with enough time, enough energy to do other things that I want to do,” says the empty nester, who has three adult children, Madeleine, 30, Peter, 28, and John, 24, with his wife of 32 years, Evelyn McGee Colbert.

Aside from writing a new Lord of the Rings movie with his son Peter, which the superfan says has been in the works for years, Colbert isn’t quite sure what he’ll do next. “The show’s like a flaming toboggan ride every day and the trick is to not hit any trees on your way down the mountain before 12:30,” he says during his PEOPLE interview in early April.

Continuing, “There’s so much to think about to do the show. So I don’t have much better of an answer than most college seniors do, which is I’ve got to finish this first, because it takes almost the entirety of my brain to do this show. So we’ll land this plane and we’ll check out the view from there.”

With a laugh, he adds, “But I’m available. Yes.”

Growing up the youngest of 11 children to Lorna, a homemaker turned businesswoman, and James, a doctor and medical school vice president, Colbert “got the bug of wanting to perform” from his mother, who studied acting. “She taught us how to faint without hurting yourself,” he says. “The trick is go, ankle, knee, hip, rib, shoulder. The arm gets thrown out last.”

Colbert had “a great time” acting in a high school production, but couldn’t envision how he could make comedy a career. “I grew up on a dirt road in South Carolina. With acting, you can go to acting school or take acting classes, you audition. How do you go into comedy? That’s so vague and so strange.” He majored in theater at Northwestern University, but once he saw the Harold improv in Chicago, he had a “deep feeling” that improv was what he “had to do,” he says, “It wasn’t just that I was lazy and you didn’t have to learn lines — but that was attractive. I loved it.”

He picked up lunch shifts as a waiter so he could perform at night. Around that time, he fell in love with Evelyn, who was raised in his hometown. After asking her on a date, he says he couldn’t believe “Evie McGee’s going out with me!”

Colbert later toured with Second City as Steve Carell’s understudy and worked on sketch comedy shows like Exit 57 and Saturday Night Live as a freelance writer. The only time he had a “deep panic” about his career choice was after he and Evelyn married in 1993.

“I thought, ‘Oh, wait, I kind of want to have children and was this going to work out? I’ll never be able to afford a house or a family or a car. Am I good enough to do this?’” He was medicated for a “short time” to “put out the fire in my gearbox,” he says.

Ultimately, his friend Stephen Conley helped him shake that “inexplicable panic,” he says. “He called me up and goes, ‘I hear you’re freaking out. Just lie down and give up if you feel like you have to give up because we all love you. We’ll take care of you.’ I don’t know why, but it was exactly the right thing to say. This isn’t going to kill you.”

He began appearing on The Daily Show in 1997, and in 2000, with Jon Stewart as the host, his air time increased. Colbert says he “flew back” to work with Stewart after he finished his writing, starring and producing a TV series with Amy Sedaris, Strangers with Candy.

“Here’s the thing, The Daily Show with Craig Kilborn was good. It really made a name for itself,” says Colbert. “But when Jon came in, it turned into a totally different beast. He turned it into something where he invited us to do satire, which is not quite the same thing as jokes about current events. He invited us to do satire, and that was really attractive to me.”

Five years and three Emmys later, Colbert landed his own spinoff, The Colbert Report, playing a fictional conservative political pundit. It ran for nine seasons and, in 2013, broke The Daily Show’s winning streak at the Emmys for Outstanding Variety Series. When Colbert decided to end the show in 2014, it was never his intention to host another one. In fact, when he was offered the job to take over The Late Show from Letterman, he spent four months in therapy before accepting it.

“I’m an actor and a writer. I became a writer because nobody would cast me in anything and I had to write for myself. I always imagined that’s what I’d be doing after The Colbert Report because that was an acting job. When I got this, at first I was like, ‘No, I can’t do that job. I’m not a standup. I’ve never been myself,’” he recalls.

But it was Colbert’s ability to show his true self that endeared him to fans. During his time on The Late Show, he opened up about grief and faith in a way that earned him viral recognition. In 2019, he spoke with CNN’s Anderson Cooper about the death of his father and two brothers, Peter and Paul, who died in an plane crash in 1974.

“Ten million people had seen [the interview] in the first 24 hours or something,” Colbert says. “I was very surprised because it’s not something that I had talked about publicly and it felt innate to my view of the world, but I didn’t realize that that experience would be so meaningful to other people, because so many other people experienced it. It seems obvious and a very simple thing to realize, but it did take me by surprise.”

Two years later, his interview with actor Andrew Garfield, in which they discussed Garfield’s late mother, also gained online attention. “I try not to lead with grief or faith because that’s not my gig,” Colbert says. “But if that’s on someone’s mind or if that’s part of the story that they want to tell, I’m open to that, and that’s an important distinction to me.”

Colbert is also known for his political commentary. When asked if he’ll miss being a part of that daily conversation, he’s quick to say, “I’ll never stop caring about my country. I’m a perfectly fine fan of me, but I am not of the opinion that if my voice is missing from the national conversation, the republic will turn awry.”

Off air, Colbert enjoys fishing, cooking, building boats and spending time with his family. This stage of fatherhood, he says, is “the best.”

“To lose an argument with an adult child over something you thought you knew about. I mean, if you can take it, it’s pretty great,” he says.

And his final week of shows will be filled with family celebrations:  his son John’s college graduation and his brother Tommy’s wedding. “I’m glad a lot of the week is not about me,” he says. “It’s about the people I love more.”

Colbert’s final signoff on The Late Show on May 21 will be “something simple,” he says, much like his wish for how the show will be remembered by fans.

“I hope they laughed. I hope they felt better at the end of the day,” he says. “I mean, that’s it. We’re there. We’re the last thing you see. A lot of things happen in a day, but we bat last, and so we get the last take that people hear before they go to bed, and I hope it made their day better.”

The last episode of The Late Show with Stephen Colbert will air on Thursday, May 21 at 11:35 p.m. ET on CBS.

For more on Stephen Colbert, pick up the new issue of PEOPLE.